[ CAS No. 69-78-3 ] {[proInfo.proName]}

Name: 69-78-3|5,5'-Disulfanediylbis(2-nitrobenzoic acid)|98%
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SKU: A146608
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Quality Control of [ 69-78-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 69-78-3 ]

SDS Specification

Alternatived Products of [ 69-78-3 ]

Product Details of [ 69-78-3 ]

CAS No. :	69-78-3	MDL No. :	MFCD00007140
Formula :	C₁₄H₈N₂O₈S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KIUMMUBSPKGMOY-UHFFFAOYSA-N
M.W :	396.35	Pubchem ID :	6254
Synonyms :	Ellman’s Reagent	Chemical Name :	5,5'-Disulfanediylbis(2-nitrobenzoic acid)

Calculated chemistry of [ 69-78-3 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	7
Num. H-bond acceptors :	8.0
Num. H-bond donors :	2.0
Molar Refractivity :	96.16
TPSA :	216.84 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.04
Log Po/w (XLOGP3) :	2.74
Log Po/w (WLOGP) :	3.7
Log Po/w (MLOGP) :	1.13
Log Po/w (SILICOS-IT) :	-1.73
Consensus Log Po/w :	1.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.11

Water Solubility

Log S (ESOL) :	-3.9
Solubility :	0.0495 mg/ml ; 0.000125 mol/l
Class :	Soluble
Log S (Ali) :	-6.95
Solubility :	0.0000447 mg/ml ; 0.000000113 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-2.57
Solubility :	1.07 mg/ml ; 0.0027 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.69

Safety of [ 69-78-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 69-78-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 69-78-3 ]
Downstream synthetic route of [ 69-78-3 ]

[ 69-78-3 ] Synthesis Path-Upstream 1~5

1
[ 15139-21-6 ]
[ 69-78-3 ]

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, # 23, p. 7059 - 7065
[2] Journal of the American Chemical Society, 1985, vol. 107, # 23, p. 6634 - 6639
[3] Journal of Organic Chemistry, 1999, vol. 64, # 3, p. 832 - 835
[4] Journal of the American Chemical Society, 2005, vol. 127, # 33, p. 11588 - 11589
[5] Catalysis Letters, 2010, vol. 138, # 1-2, p. 62 - 67
[6] Macromolecular Bioscience, 2010, vol. 10, # 12, p. 1505 - 1516
[7] Soft Matter, 2011, vol. 7, # 6, p. 2521 - 2529
[8] Soft Matter, 2014, vol. 10, # 19, p. 3374 - 3385
[9] Asian Journal of Chemistry, 2015, vol. 27, # 10, p. 3799 - 3802
[10] Journal of the American Chemical Society, 2004, vol. 126, # 50, p. 16395 - 16404
[11] Journal of the American Chemical Society, 2017, vol. 139, # 4, p. 1472 - 1484

2
[ 80-15-9 ]
[ 15139-21-6 ]
[ 69-78-3 ]
[ 617-94-7 ]

Reference： [1] RSC Advances, 2014, vol. 4, # 48, p. 25040 - 25050
[2] Asian Journal of Chemistry, 2015, vol. 27, # 7, p. 2665 - 2668

3
[ 77874-90-9 ]
[ 69-78-3 ]

Reference： [1] Journal of the American Chemical Society, 1988, vol. 110, # 9, p. 2914 - 2919

4
[ 75-91-2 ]
[ 15139-21-6 ]
[ 69-78-3 ]
[ 75-65-0 ]

Reference： [1] Journal of the American Chemical Society, 1990, vol. 112, # 14, p. 5647 - 5648

5
[ 2516-95-2 ]
[ 69-78-3 ]

Reference： [1] Archives of Biochemistry, 1959, vol. 82, p. 70,71

[ 69-78-3 ] Synthesis Path-Downstream 1~89

1
[ 2516-95-2 ]
[ 69-78-3 ]

Reference： [1]Archives of Biochemistry,1959,vol. 82,p. 70,71

2
[ 109-99-9 ]
[ 69-78-3 ]
[ 105728-35-6 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

3
[ 75-91-2 ]
[ 15139-21-6 ]
[ 69-78-3 ]
[ 75-65-0 ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 5647 - 5648

4
[ 79-24-3 ]
[ 69-78-3 ]
[ 18430-02-9 ]
2-Nitro-5-(1-nitro-ethylsulfanyl)-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

5
[ 75-52-5 ]
[ 69-78-3 ]
[ 18430-02-9 ]
2-Nitro-5-nitromethylsulfanyl-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

6
[ 74-90-8 ]
[ 69-78-3 ]
[ 30211-77-9 ]
[ 18430-02-9 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

7
[ 921-01-7 ]
[ 69-78-3 ]
[ 15139-21-6 ]
5-(2-Amino-2-carboxy-ethyldisulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1101 - 1105

8
[ 1001-58-7 ]
[ 69-78-3 ]
[ 149997-68-2 ]

Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 506 - 512

9
[ 79-46-9 ]
[ 69-78-3 ]
[ 18430-02-9 ]
5-(1-Methyl-1-nitro-ethylsulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

10
[ 3075-23-8 ]
[ 69-78-3 ]
[ 18430-02-9 ]
5-(1-Ethylsulfanylcarbonyl-2-oxo-propylsulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

11
[ 815-68-9 ]
[ 69-78-3 ]
[ 18430-02-9 ]
5-(1,1-Diacetyl-2-oxo-propylsulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

12
[ 6186-89-6 ]
[ 69-78-3 ]
[ 18430-02-9 ]
2-(3-Carboxy-4-nitro-phenylsulfanyl)-malonic acid ethyl ester methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

13
[ 2885-00-9 ]
[ 69-78-3 ]
[ 136860-97-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2019 - 2021

14
[ 13133-62-5 ]
[ 69-78-3 ]
[ 18430-02-9 ]
[ 882-33-7 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5860 - 5866

15
[ 7218-04-4 ]
[ 69-78-3 ]
[ 15139-21-6 ]
5-(2-Acetylamino-2-carboxy-ethyldisulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1101 - 1105

16
[ 69-78-3 ]
[ 20733-16-8 ]
[ 629-45-8 ]
[ 18430-02-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5860 - 5866

17
[ 52-66-4 ]
[ 69-78-3 ]
[ 15139-21-6 ]
5-(2-Amino-2-carboxy-1,1-dimethyl-ethyldisulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1101 - 1105

18
[ 69-78-3 ]
[ 597-82-0 ]
5,5'-Dithiobis(2-nitrobenzoesaeure) [ No CAS ]
[ 18430-02-9 ]

Reference： [1]Phosphorus, Sulfur and Silicon and the Related Elements,1989,vol. 44,p. 39 - 52

19
[ 69-78-3 ]
[ 134257-67-3 ]
[ 822-27-5 ]
[ 18430-02-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5860 - 5866

20
[ 69-78-3 ]
[ 29869-27-0 ]
[ 5586-15-2 ]
[ 18430-02-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5860 - 5866

21
[ 69-78-3 ]
[ 7161-73-1 ]
[ 77874-90-9 ]
C₁₂H₁₆N₂O₄S₂*I^(1-) [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1987,vol. 35,p. 1491 - 1496

22
[ 69-78-3 ]
[ 79246-00-7 ]
[ 85908-82-3 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 2598 - 2600

23
[ 69-78-3 ]
(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3-thiol anion [ No CAS ]
[ 39879-87-3 ]
[ 18430-02-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5860 - 5866

24
[ 69-78-3 ]
[ 40055-99-0 ]
[ 40055-98-9 ]
[ 18430-02-9 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5860 - 5866

25
[ 69-78-3 ]
[ 118599-21-6 ]
6-nitro-3-<(4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenyldisulfamyl> benzoic acid [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 17 - 23

26
[ 69-78-3 ]
[ 152540-05-1 ]
3-(4-(((4-Nitro-3-carboxyphenyl)dithio)methyl)phenyl)-3-(trifluoromethyl)-3H-diazirine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7598 - 7601

27
[ 69-78-3 ]
[ 15139-21-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium tetrahydroborate; In ethanol; water; at 0 - 20℃;	In a 50 mL one-neck round-bottom flask, 5,5?-dithiobis(2-nitrobenzoicacid) (420 mg, 1.06 mmol, 1 equiv) was slurried in 80%EtOH (v/v, 5 mL) cooled to 0 C with an ice bath. NaBH4 (320 mg,8.46 mmol, 8 equiv) was dissolved in distilled water (2 mL) andslowly added dropwise through an addition funnel (CAUTIONVigorous effervescence develops). The resulting dark redmixture was stirred at r.t. until gas evolution subsided. Afterdilution with EtOH (5 mL) and distilled water (5 mL), themixture was acidified with 2 N HCl, extracted with CH2Cl2 (3 ×20 mL), and the pooled organic layers were washed with distilledwater (3 × 50 mL) and brine (3 × 50 mL). The yelloworganic solution was dried over Na2SO4, filtered, and concentratedto dryness to afford the desired thiol as a bright orangesolid (410 mg, 97% yield); mp 143-145 C. 1H NMR (400 MHz,CDCl3): delta = 3.84 (1 H, s, SH), 5.77 (1 H, br, COOH), 7.48 (1 H, dd, J= 8.5, 2.1 Hz, H-4), 7.63 (1 H, d, J = 2.1 Hz, H-6), 7.86 (1 H, d, J =8.5 Hz, H-3). 13C NMR (100 MHz, CDCl3): delta = 125.2 (C-3), 126.6(C-1), 128.8 (C-6), 128.9 (C-4), 141.6 (C-5), 146.5 (C-2), 165.3(COOH). MS: m/z = 200.1 [M + H]+; 198.0 [M - H]-. Anal. Calcdfor C7H5NO4S: C, 42.21; H, 2.53; N, 7.03. Found: C, 42.19; H,2.55; N, 7.07.
		<strong>[69-78-3]5,5'-Dithiobis(2-nitrobenzoic acid)</strong> (4.025 g, 10.155 mmol) was dissolved in ethanol (300 ml). The solution was heated to 70 C. and sodium borohydride (1.537 g, 40.62 mmol) was added slowly. The solution was refluxed for 1 hour. The mixture was diluted with water (250 ml), acidified with HCl 37% in water and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The crude product was used in the next step without further purification (4 g, 99%).MS: [M-H]-=198
140 mg	With hydrogenchloride; 2-amino-2-hydroxymethyl-1,3-propanediol; diothiothreitol; In water; at 20℃; for 0.166667h;pH 8;	5,5'-Dithio-bis-(2-nitrobenzoic acid) (12) (0.5 g, 1.26 mmol) was dissolved in aqueous solution of 0.5 M Tris base (25 mL), and the pH was adjusted to pH 8.0 by addition of 6 M HCl. DL Dithiothreitol (0.28 g, 1.78 mmol) was added. The orange-red solution was stirred for 10 min at room temperature and extracted with EtOAc (6 x 6 mL). The aqueous layer was acidified to pH 1.5 by addition of 6 M HCl. The residual EtOAc was eliminated by bubbling nitrogen through the solution which was kept after that in the fridge at 4 C for 14 h. The orange solid of TNB (13) (140 mg) was precipitated, collected by filtration and dried. ESI - MS, m/z: 198 [M - H]-.

	With ethylenediaminetetraacetic acid; Fasciola gigantica selenocysteine containing thioredoxin glutathione reductase; NADPH; sodium chloride; In aq. phosphate buffer; at 25℃;pH 7.2;Enzymatic reaction;Catalytic behavior; Kinetics;	TrxR and GR activities of FgTGRsec, FgTGR and NTD-FgTGRsec were performed in a Cary 50 (Varian) spectrophotometer at 25C based on the methods described by Kuntz et al. [7]. The TrxR activity was determined by the 5,5?-diothiobis(2-nitrobenzoic acid) (DTNB) reduction assay. The assay solution contained 1muM recombinant enzyme, 200muM NADPH and 10mM EDTA in 20mM phosphate buffer (pH7.2), containing 150mM NaCl. The DTNB concentration was varied from 0.5mM to 5mM. The increase in absorbance at 412nm during the first 3min was monitored, and the extinction coefficient of 13.6 mM-1cm-1 for 5-thionitrobenzoic acid (TNB) was used for calculation of activity. (0010) The GR activity was determined using GSSG. The reaction mixture contained 1muM recombinant enzyme, 200muM NADPH and 1mM EDTA in 20mM phosphate buffer (pH7.2) and 150mM NaCl. The GSSG concentration was varied from 0.5muM to 5muM. The decrease in NADPH consumption at 340 nm during the first 3min was monitored, and the extinction coefficient of 6.22 mM-1cm-1 for NADPH was used for calculation of activity.
	With thioarginine; arginase; In glycerol; at 20℃; for 0.5h;pH 9;Enzymatic reaction;	To measure Vmax and Km, thioarginine solutions were freshly prepared in Tris buffer (50 mMTris, 50 mMNaCl, 10% glycerol, pH = 9, 1mM DTNB). Subsequently, 30 muL of an arginase (500nM) solution was added to 20 muL of thioarginine solution with varying concentration (0.05, 0.10, 0.20, 0.50, 1.0, 2.0, 5.0 mM) at room temperature. The release of the TNB was monitored for 30 min at 30 sec intervals. The initial rate was calculated based on the absorbance data between 5 min and 10 min.During the time frame of the assay, the reaction was kept at less than 10% conversion for all concentrations of thioarginine used.By fitting the data to the Michaelis-Menten equation, the Michaelis constant (Km) and maximum velocity (Vmax) were determined.(Figure S2). The results are presented in Table S1.

Reference： [1]Synlett,2016,vol. 27,p. 2447 - 2450
[2]Journal of the American Chemical Society,1985,vol. 107,p. 6634 - 6639
[3]Journal of the American Chemical Society,1998,vol. 120,p. 7226 - 7238
[4]Analytical Chemistry,2003,vol. 75,p. 3681 - 3687
[5]Biological and Pharmaceutical Bulletin,2006,vol. 29,p. 1659 - 1670
[6]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 6623 - 6630
[7]Catalysis Letters,2010,vol. 138,p. 62 - 67
[8]Patent: US2010/280268,2010,A1 .Location in patent: Page/Page column 35
[9]Drug Metabolism and Disposition,2010,vol. 38,p. 898 - 904
[10]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3282 - 3285
[11]Biochemistry,2011,vol. 50,p. 194 - 206
[12]Journal of Biological Chemistry,2011,vol. 286,p. 7812 - 7821
[13]Biochimica et Biophysica Acta - General Subjects,2012,vol. 1820,p. 1859 - 1866
[14]Journal of Materials Chemistry A,2013,vol. 1,p. 10148 - 10154
[15]Inorganica Chimica Acta,2014,vol. 418,p. 51 - 58
[16]Asian Journal of Chemistry,2014,vol. 26,p. 3733 - 3735
[17]Chemical Communications,2015,vol. 51,p. 10953 - 10956
[18]Journal of the American Chemical Society,2014,vol. 136,p. 15865 - 15868
[19]Chemistry - A European Journal,2017,vol. 23,p. 8585 - 8589
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[22]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3939 - 3946
[23]Chemical Communications,2019,vol. 55,p. 9797 - 9800

28
[ 69-78-3 ]
[ 54375-78-9 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 6586 - 6587

29
[ 69-78-3 ]
[ 18430-02-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1986,vol. 34,p. 1075 - 1079
[2]Organic and Biomolecular Chemistry,2009,vol. 7,p. 2958 - 2966

30
[ 69-78-3 ]
[ 18430-02-9 ]
2-Nitro-5-sulfino-benzoic acid anion [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 5439 - 5447
[2]Journal of the American Chemical Society,1981,vol. 103,p. 5439 - 5447
[3]Journal of the American Chemical Society,1981,vol. 103,p. 5439 - 5447

31
[ 69-78-3 ]
[ 552-24-9 ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 365 - 366

32
[ 69-78-3 ]
[ 18430-02-9 ]

Reference： [1]Tetrahedron Letters,1984,vol. 25,p. 317 - 320

33
[ 69-78-3 ]
[ 77874-90-9 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6477 - 6479
[2]Journal of the American Chemical Society,1988,vol. 110,p. 2914 - 2919
[3]Journal of the American Chemical Society,1980,vol. 102,p. 754 - 762
[4]Organic Letters,2004,vol. 6,p. 3809 - 3812
[5]Chemistry - A European Journal,2014,vol. 20,p. 8965 - 8972
[6]ACS Chemical Neuroscience,2018,vol. 9,p. 800 - 808

34
[ 69-78-3 ]
[ 77874-90-9 ]
C₇H₃NO₅S^(2-) [ No CAS ]
C₇H₃NO₆S^(2-) [ No CAS ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1980,vol. 9,p. 127 - 136

35
[ 69-78-3 ]
[ 105728-34-5 ]
[ 105762-12-7 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

36
[ 15139-21-6 ]
[ 69-78-3 ]

Yield	Reaction Conditions	Operation in experiment
		The catalytic activity was assayed according to a modified method reported by Hilvert and Wu11. The typical assay process of glutathione peroxidase activity in solvent mixture of PBS and ethanol was shown as follows: The reaction was carried out at 25 C in a 1mL quartz cuvette, 700 muL solvent mixture of PBS and ethanol and 100 muL of the catalyst (ADA-Te-OH) (0.025 mM) were added and then 100 muL of the 3-carboxyl-4-nitrobenzenethiol solution (1 mM) was added. The mixture in the quartz cuvette was pre-incubated at the 25 C for 3 min. Finally, the reaction was initiated by the addition of 100 mL of H2O2 (2 mM) and the absorption decrease of 3-carboxyl-4-nitrobenzenethiol at 410 nm (epsilon410 = 13600 M-1 cm-1. pH = 7.0) was monitored by a Shimadzu 2600 UV-visible-NIR spectrophotometer. Appropriate control of the non-enzymatic reaction was performed and was subtracted from the catalyzed reaction. The glutathione peroxidase activities in solvent mixture of PBS and other cosolvents were assayed similarly except ethanol was replaced by other co-solvents

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065
[2]Journal of the American Chemical Society,1985,vol. 107,p. 6634 - 6639
[3]Journal of Organic Chemistry,1999,vol. 64,p. 832 - 835
[4]Journal of the American Chemical Society,2005,vol. 127,p. 11588 - 11589
[5]Catalysis Letters,2010,vol. 138,p. 62 - 67
[6]Macromolecular Bioscience,2010,vol. 10,p. 1505 - 1516
[7]Soft Matter,2011,vol. 7,p. 2521 - 2529
[8]Soft Matter,2014,vol. 10,p. 3374 - 3385
[9]Asian Journal of Chemistry,2015,vol. 27,p. 3799 - 3802
[10]Journal of the American Chemical Society,2004,vol. 126,p. 16395 - 16404
[11]Journal of the American Chemical Society,2017,vol. 139,p. 1472 - 1484

37
[ 77874-90-9 ]
[ 69-78-3 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2914 - 2919

38
[ 69-78-3 ]
[ 3411-58-3 ]
[ 15139-21-6 ]
5-(2-Amino-2-ethoxycarbonyl-ethyldisulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1981,vol. 29,p. 1101 - 1105

39
[ 69-78-3 ]
[ 105-56-6 ]
[ 18430-02-9 ]
5-((Z)-1-Cyano-2-ethoxy-2-hydroxy-vinylsulfanyl)-2-nitro-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 7059 - 7065

40
[ 27565-41-9 ]
[ 69-78-3 ]
[ 15139-21-6 ]

Reference： [1]Antimicrobial Agents and Chemotherapy,2001,vol. 45,p. 1868 - 1871

41
[ 69-78-3 ]
5-thio-2-nitrobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70-78%	2-(N,N-dimethylamino)athanol;	Xanthenyl-protected Ellman's reagent 2-nitro-5-S-(9H-xanthene-9-yl)thiobenzoic acid [S-Xan-TNB] Xanthenyl-protected Ellman's reagent for use in the reaction scheme as shown in was prepared on a 20 g scale from commercially available <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> (DTNB) by closely following the procedure of Annis et al. The reaction scheme for preparing the protected Ellman's reagent is shown in . Reduction of DTNB with beta-mercaptoethylamine in the presence of N,N-dimethyl-N-(2-hydroxyethyl)amine gave 2-nitro-5-thiobenzoic acid (TNB) in essentially quantitative yield. This material was reacted directly with 9H-xanthen-9-ol to provide the title product S-Xan-TNB in 70-78% yield, after crystallization from CH2Cl2:MeOH with addition of hexane, mp 174-176 C. dec, (literature 172, Annis et al). TLC, single spot (CHCl3:MeOH:AcOH (85:10:5 v/v/v)) Rf 0.77; (CHCl3:MeOH:AcOH (90:8:2 v/v/v)) Rf 0.67; (EtOAc:Hexane:AcOH (1:1:0.01 v/v/v)) Rf 0.44. Elemental Analysis: theory C, 63.32; H, 3.45; N, 3.69; S, 8.45; found: C, 62.64; H, 3.58; N, 3.79; S, 8.53. ES-MS calc C20H13NO5S: 379.05 found (negative mode m/z) 378.6 (M-H)-.

Reference： [1]Patent: US2006/47105,2006,A1

42
[ 69-78-3 ]
[ 37880-96-9 ]
C₁₂H₁₇N₂O₄S₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]
[ 15139-21-6 ]

Reference： [1]Analytical Chemistry,2007,vol. 79,p. 3409 - 3415

43
[ 69-78-3 ]
(6R,7R)-3-(((3-carboxy-4-nitrophenyl)thio)methyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid [ No CAS ]

Reference： [1]Antimicrobial Agents and Chemotherapy,2001,vol. 45,p. 1868 - 1871
[2]Synlett,2016,vol. 27,p. 2447 - 2450
[3]Synlett,2016,vol. 27,p. 2447 - 2450

44
[ 69-78-3 ]
[ 350578-43-7 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 5401 - 5406

45
[ 69-78-3 ]
(S)-2-Amino-4-[(R)-1-(carboxymethyl-carbamoyl)-2-(3-dimethylcarbamoyl-4-nitro-phenyldisulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 5401 - 5406

46
[ 69-78-3 ]
(S)-7,19-Dinitro-9,17-dioxo-2,3-dithia-10,16-diaza-tricyclo[16.3.1.1^4,8]tricosa-1⁽²¹⁾,4⁽²³⁾,5,7,18⁽²²⁾,19-hexaene-11-carboxylic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 7226 - 7238

47
[ 69-78-3 ]
ethyl 3-(3-carboxy-4-nitrophenyldithio)propionthioimidate ester hydrochloride [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1993,vol. 82,p. 506 - 512

48
[ 69-78-3 ]
[ 105728-38-9 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

49
[ 69-78-3 ]
4-(3-Formyl-4-nitro-phenylsulfanyl)-butyryl chloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

50
[ 69-78-3 ]
[ 105728-37-8 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

51
[ 69-78-3 ]
[ 105728-36-7 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

52
[ 69-78-3 ]
[ 105728-39-0 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

53
[ 69-78-3 ]
[ 105695-41-8 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

54
[ 69-78-3 ]
{2-Amino-5-[3-(cyclohexyl-methyl-carbamoyl)-propylsulfanyl]-benzylamino}-acetic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

55
[ 69-78-3 ]
[ 105695-42-9 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

56
[ 69-78-3 ]
[1-{5-[3-(Cyclohexyl-methyl-carbamoyl)-propylsulfanyl]-2-nitro-phenyl}-meth-(E)-ylidene]-amino}-acetic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

57
[ 69-78-3 ]
[ 1071155-81-1 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

58
[ 69-78-3 ]
[ 105695-43-0 ]

Reference： [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 303 - 318

59
Cy₅-Cys-Gly-Leu-Asp-Lys-Arg-Gly-Cys-Gly-NH₂ [ No CAS ]
[ 69-78-3 ]
Cy₅-Cys(TNB)-Gly-Leu-Asp-Lys-Arg-Gly-Cys(TNB)-Gly-NH₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water;pH 7.27;Aqueous phosphate buffer; Aqueous EDTA buffer;	A sample of Cy5-Cys-Gly-Leu-Asp-Lys-Arg-Gly-Cys-Gly-NH2 was dissolved in [100MM] sodium phosphate buffer; [1 MM] EDTA pH 7.27 (stock buffer) to afford a 0. 3muM peptide stock by UVNIS at 650nm. 0. [3PM] peptide stock (40mul) and [10MM] 5,5'-dithiobis (2-nitrobenzoic acid (DTNB) in [100MM] sodium phosphate buffer; [1 MM] EDTA pH 7.27 [(501L1)] were mixed together in stock buffer (910mul) to afford a green solution. The absorbance [AT 412NM] (due to generation of TNB2-) was recorded against a DTNB [BLANK [10MM] DTNB stock [(50GEL)] in stock buffer (950mul ]. Using the known molar absorption coefficient of TNB2- (14150M-1cm-1), the thiol concentration was determined as 655muM, approximately twice the peptide concentration, confirming two free thiol groups. [SH] [=] [A412nm (sample)- A412nm [(REFERENCE)/S] [(TNB2-)]

Reference： [1]Patent: WO2004/11556,2004,A1 .Location in patent: Page 19

60
[ 69-78-3 ]
[ 124-40-3 ]
[ 350578-43-7 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In DMF (N,N-dimethyl-formamide); at 0℃; for 8h;	DMF (2.8 mL) containing <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> (515 mg, 1.4 mmol) was mixed with dimethylamine (343 mg, 3.0 mmol), DCC (867 mg, 3.0 mmol), and HOBt.H2O (214 mg, 1.4 mmol), and then stirred for eight hours while cooling on ice. On completion of the reaction, the reaction solution was concentrated, dissolved in ethyl acetate, and successively washed with an aqueous 10% citric acid solution, an aqueous 4% sodium bicarbonate solution, and saturated saline. After drying over MgSO4, ethyl acetate was removed by evaporation. The residue was vacuum-dried and purified using flash silica gel chromatography (4×30 cm, 1% methanol/chloroform) to obtain 5,5'-dithiobis(2-nitrobenzoic acid dimethylamide). DMF (2 ml) containing cyclo(-L-Am7(Ac)-D-Tyr(Me)-L-Ile-D-Pro-) (130 mg, 0.22 mmol) was mixed with 5,5'-dithiobis(2-nitrobenzoic acid dimethylamide) (198 mg, 0.44 mmol) and methanolic ammonia (10 eq.), and then stirred for 6 hours. The reaction solution was concentrated, dissolved in a small amount of DMF, and purified by HPLC (column: YMC-Pack ODS-A 10×250 mm) to obtain the title compound. The yield was 13 mg (9.3%). HPLC retention time: 9.5 min; HRMS (FAB, dithiodiethanol), 771.3201 [M+H], C37H50O8N6S2 (771.3210).

Reference： [1]Patent: US2005/277583,2005,A1 .Location in patent: Page/Page column 15

61
[ 69-78-3 ]
[ 109-78-4 ]
5,5'-dithiobis(2-nitrobenzoate)propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane; ethanol; chloroform;	Synthesis of 5,5'-dithiobis(2-nitrobenzoate)propionitrile <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> [Ellman's reagent] (500 mg,1.26 mmol) was dissolved in 4.0 ml dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol) were added. The reaction mixture was stirred overnight at room temperature. The urea precipitate was removed by centrifugation. The dioxane was removed on rotary evaporator. The residue was washed with saturated bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 ml/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent afforded 233 mg (36.8%) product as a yellow oil. TLC (silica: 5% methanol in chloroform; rf=0.51). H1 NMR ? 8.05 (d, 4H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).
233 mg (36.8%)	In 1,4-dioxane; ethanol; chloroform;	Example 1 Synthesis of 5,5'-Dithiobis(2-nitrobenzoate)propionitrile <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> (500 mg, 1.26 mmol, Aldrich Chemical Company) was taken up in 4.0 mL dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol, Aldrich Chemical Company) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol, Aldrich Chemical Company) were added. The reaction mixture was stirred overnight at room temperature. The precipitate was removed by centrifugation, and the solvent concentrated under reduced pressure. The residue was washed with saturated sodium bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal (aspirator) yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 mL/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent (aspirator) afforded 233 mg (36.8%) of 5,5'-dithiobis(2-nitrobenzoate)propionitrile as a yellow oil. TLC (silica: 5% methanol in chloroform; Rf=0.51). H1 NMR 8.05 (d, 4 H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).
233 mg (36.8%)	In 1,4-dioxane; ethanol; chloroform;	Example 11 Synthesis of 5,5'-Dithiobis(2-nitrobenzoate)propionitrile <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> (500 mg, 1.26 mmol, Aldrich Chemical Company) was taken up in 4.0 mL dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol, Aldrich Chemical Company) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol, Aldrich Chemical Company) were added. The reaction mixture was stirred overnight at room temperature. The precipitate was removed by centrifugation, and the solvent concentrated under reduced pressure. The residue was washed with saturated sodium bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal (aspirator) yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 mL/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent (aspirator) afforded 233 mg (36.8%) of 5,5'-dithiobis(2-nitrobenzoate)propionitrile as a yellow oil. TLC (silica: 5% methanol in chloroform; Rf=0.51). H1NMR ? 8.05 (d, 4 H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).

	In 1,4-dioxane; methanol; ethanol; chloroform;	Synthesis of Activated Disulfide Containing Co-monomers Synthesis of 5,5'-dithiobis(2-nitrobenzoate)propionitrile: <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> [Ellman's reagent] (500 mg, 1.26 mmol) was dissolved in 4.0 ml dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol) were added. The reaction mixture was stirred overnight at room temperature. The urea precipitate was removed by centrifugation. The dioxane was removed on rotary evaporator. The residue was washed with saturated bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 ml/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent afforded 233 mg (36.8%) product as a yellow oil. TLC (silica: 5% methanol in chloroform; rf=0.51). H1 NMR delta8.05 (d, 4 H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).
	In 1,4-dioxane; methanol; ethanol; chloroform;	Synthesis of Activated Disulfide Containing Co-monomers Synthesis of 5,5'-dithiobis(2-nitrobenzoate)propionitrile: <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> [Ellman's reagent] (500 mg, 1.26 mmol) was dissolved in 4.0 ml dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol) were added. The reaction mixture was stirred overnight at room temperature. The urea precipitate was removed by centrifugation. The dioxane was removed on rotary evaporator. The residue was washed with saturated bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 mn), flow rate=9.0 ml/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent afforded 233 mg (36.8%) product as a yellow oil. TLC (silica: 5% methanol in chloroform; rf=0.51). H1 NMR delta8.05 (d, 4 H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).
	In 1,4-dioxane; methanol; ethanol; chloroform;	Synthesis of Activated Disulfide Containing Co-monomers Synthesis of 5,5'-dithiobis(2-nitrobenzoate)propionitrile: <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> [Ellman's reagent] (500 mg,1.26 mmol) was dissolved in 4.0 ml dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol) were added. The reaction mixture was stirred overnight at room temperature. The urea precipitate was removed by centrifugation. The dioxane was removed on rotary evaporator. The residue was washed with saturated bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 ml/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent afforded 233 mg (36.8%) product as a yellow oil. TLC (silica: 5% methanol in chloroform; rf=0.51). H1NMR ? 8.05 (d, 4H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).
	In 1,4-dioxane; ethanol; chloroform;	Synthesis of 5,5'-dithiobis(2-nitrobenzoate)propionitrile <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> [Ellman's reagent] (500 mg,1.26 mmol) was dissolved in 4.0 ml dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol) were added. The reaction mixture was stirred overnight at RT. The urea precipitate was removed by centrifugation. The dioxane was removed on rotary evaporator. The residue was washed with saturated bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 ml/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent afforded 233 mg (36.8%) product as a yellow oil. TLC (silica: 5% methanol in chloroform; rf=0.51). H1 NMR ?8.05 (d, 4 H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).
233 mg (36.8%)	In 1,4-dioxane; ethanol; chloroform;	Example 11 Synthesis of 5,5'-Dithiobis(2-nitrobenzoate)propionitrile <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> (500 mg, 1.26 mmol, Aldrich Chemical Company) was taken up in 4.0 mL dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol, Aldrich Chemical Company) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol, Aldrich Chemical Company) were added. The reaction mixture was stirred overnight at room temperature. The precipitate was removed by centrifugation, and the solvent concentrated under reduced pressure. The residue was washed with saturated sodium bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal (aspirator) yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 mL/min, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent (aspirator) afforded 233 mg (36.8%) of 5,5'-dithiobis(2-nitrobenzoate)propionitrile as a yellow oil. TLC (silica: 5% methanol in chloroform; Rf=0.51). H1NMR ? 8.05 (d, 4 H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).
	In 1,4-dioxane; ethanol; chloroform;	Synthesis of 5,5'-dithiobis(2-nitrobenzoate)propionitrile: <strong>[69-78-3]5,5'-dithiobis(2-nitrobenzoic acid)</strong> [Ellman's reagent] (500 mg,1.26 mmol) was dissolved in 4.0 ml dioxane. Dicylohexylcarbodiimide (540 mg, 2.6 mmol) and 3-hydroxypropionitrile (240 muL, 188 mg, 2.60 mmol) were added. The reaction mixture was stirred overnight at room temperature. The urea precipitate was removed by centrifugation. The dioxane was removed on rotary evaporator. The residue was washed with saturated bicarbonate, water, and brine; and dried over magnesium sulfate. Solvent removal yielded 696 mg yellow/orange foam. The residue was purified using normal phase HPLC (Alltech econosil, 250*22 nm), flow rate=9.0 mlmin, mobile phase=1% ethanol in chloroform, retention time=13 min. Removal of solvent afforded 233 mg (36.8%) product as a yellow oil. TLC (silica: 5% methanol in chloroform; rf=0.51). H1NMR ?8.05 (d, 4 H), 7.75 (m, 4H), 4.55 (t, 4H), 2.85 (t, 4H).

Reference： [1]Patent: US2003/166280,2003,A1
[2]Patent: US2001/36926,2001,A1
[3]Patent: US2001/44417,2001,A1
[4]Patent: US2002/137707,2002,A1
[5]Patent: US2002/137707,2002,A1
[6]Patent: US6627616,2003,B2
[7]Patent: US2004/72785,2004,A1
[8]Patent: US2005/20518,2005,A9
[9]Patent: US2004/106567,2004,A1

62
NaHCO [ No CAS ]
[ 69-78-3 ]
[ 115215-73-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; thionyl chloride; citric acid; In methanol; dichloromethane; N,N-dimethyl-formamide;	D. Dimethyl 5,5'-Dithiobis-(2-nitrobenzoate) This compound is a lipophilic analog of <strong>[69-78-3]5,5'-dithiobis-(2-nitrobenzoic acid)</strong>, which was prepared for use as a thiol indicator as follows: A suspension containing 7.93 g (20 mmol) of <strong>[69-78-3]5,5'-dithiobis-(2-nitrobenzoic acid)</strong>, 1.2 mL of N,N-dimethylformamide, 11.7 mL of thionyl chloride, and 400 mL of dichloromethane were refluxed for 4 hours until a clear light green solution was obtained. The solvents were then evaporated in vacuo to obtain a yellow solid which was then placed under an Argon atmosphere, dissolved in 200 mL of dichloromethane, and cooled to 0. The stirred mixture was then treated with 4.03 mL of dry pyridine (50 mmol) and 30 mL of methanol. The resulting mixture was then allowed to warm to ambient temperature overnight. The reaction mixture was then successively extracted thrice with 300 mL of 5% NaHCO solution, thrice with 300 mL of 1 M citric acid, and 300 mL of brine. Drying (MgSO4), filtration and removal of solvents gave 8.29 of a yellow solid which was recrystallized in two crops from toluene as a light yellow solid in 92% yield. mp 103-104.5. Analysis: Calculated for: C, 45.28; H, 2.86; N, 6.60. Found: C, 45.74; H, 3.01; N, 6.25. PMR (60 MHz, CDCl3) delta: 3.93 (s, 6H, --O--CH3); 7.8 (s, 2H, C6 H); 7.83 (AB quartet, J=8Hz, 4H, C3 H, C4 H). IR (KRr) cm-1: 1740 STR7 Mass Spectrum: EI (70EV) m/e: 424.3 (M+, 67.7%)

Reference： [1]Patent: US5041658,1991,A

63
3'-d(GCTGA_P[NH(CH₂)2SH]TGCCG)-5', R_P configuration [ No CAS ]
[ 69-78-3 ]
3'-d(GCTGA_P[NH(CH₂)2S-(4-nitro-3-carboxybenzenethio)]TGCCG)-5', R_P configuration [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 2329 - 2331

64
3'-d(GCTGA_P[NH(CH₂)2SH]TGCCG)-5', S_P configuration [ No CAS ]
[ 69-78-3 ]
3'-d(GCTGA_P[NH(CH₂)2S-(4-nitro-3-carboxybenzenethio)]TGCCG)-5', S_P configuration [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 2329 - 2331

65
Na₁₈Au₈(thiomalate)9 [ No CAS ]
[ 69-78-3 ]
2HO₂CC₆H₃NO₂S^(1-)*8Au*7S₂CCH(SH)CH₂CS₂^(2-)=(HO₂CC₆H₃NO₂S)2Au₈(S₂CCH(SH)CH₂CS₂)7^(16-) [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1988,vol. 152,p. 261 - 264

66
2HO₂CC₆H₃NO₂S^(1-)*8Au*7S₂CCH(SH)CH₂CS₂^(2-)=(HO₂CC₆H₃NO₂S)2Au₈(S₂CCH(SH)CH₂CS₂)7^(16-) [ No CAS ]
[ 69-78-3 ]
[ 136208-74-7 ]

Reference： [1]Inorganica Chimica Acta,1988,vol. 152,p. 261 - 264

67
[ 51868-81-6 ]
[ 52-90-4 ]
[ 69-78-3 ]
Cr⁽³⁺⁾*C₁₄H₈N₂O₈S₂^(1-)*2C₃H₇NO₂S^(1-)=Cr(C₁₄H₈N₂O₈S₂)(C₃H₇NO₂S)2 [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,1996,vol. 52,p. 139 - 148

68
[ 69-78-3 ]
[ 28588-74-1 ]
C₁₂H₉NO₅S₂ [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 6623 - 6630

69
[ 69-78-3 ]
MGIEMKPHPWFFGKIPRAKAEEMLSKQRHDGAFLIRESESAPGDFSLSVKFGNDVQHFKVCRDGAGKYFLWVVKFNSLNELVDYHRSTSVSRNQQIFLRDIEQVPQQPTYVQAGSRSHHHHHH [ No CAS ]
SH₂ domain of the Grb₂ adaptor protein L₁₁₁C mutant modified with Ellman's reagent [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 1960 - 1965

70
[ 69-78-3 ]
C₅H₁₃NS [ No CAS ]
C₁₂H₁₇N₂O₄S₂⁽¹⁺⁾ [ No CAS ]
[ 18430-02-9 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 4445 - 4454

71
[ 69-78-3 ]
H-SPKMVQGSGCFGRKMDRISSSSGLG-SH [ No CAS ]
H-SPKMVQGSGCFGRKMDRISSSSGLG-S(3-carboxy-4-nitrophenyl) [ No CAS ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 3290 - 3296

72
[ 69-78-3 ]
[ 1228171-13-8 ]
[ 1228171-15-0 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 3290 - 3296

73
[ 69-78-3 ]
recombinant sterol carrier protein 2 like domain of MFE-2 (MFE-2(628-731)), mutant V₈₃C [ No CAS ]
conjugate of {recombinant sterol carrier protein 2 like domain of MFE-2 (MFE-2(628-731)), mutant V₈₃C} with 5,5'-dithio-bis(2-nitrobenzoic acid) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 5315 - 5317

74
[ 95-14-7 ]
[ 69-78-3 ]
[ 1234804-46-6 ]

Reference： [1]Synthesis,2010,p. 1485 - 1492

75
[ 69-78-3 ]
[ 204204-98-8 ]
TNB-R-138727 disulfide [ No CAS ]

Reference： [1]Drug Metabolism and Disposition,2010,vol. 38,p. 898 - 904

76
[ 69-78-3 ]
TNB-R-138727 disulfide [ No CAS ]

Reference： [1]Drug Metabolism and Disposition,2010,vol. 38,p. 898 - 904

77
[ 69-78-3 ]
GIEMKPHPWFFGKIPRAKAEEMLSKQRHDGAFLIRESESAPGDFSLSVKFGNDVQHFKVCRDGAGKYFLWVVKFNSLNELVDYHRSTSVSRNQQIFLRDIEQVPQQPTYVQAGSRSHHHHHHStop [ No CAS ]
GIEMKPHPWFFGKIPRAKAEEMLSKQRHDGAFLIRESESAPGDFSLSVKFGNDVQHFKVC(S-S-C₆H₃-4-NO₂-3-CO₂H)RDGAGKYFLWVVKFNSLNELVDYHRSTSVSRNQQIFLRDIEQVPQQPTYVQAGSRSHHHHHHStop [ No CAS ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 5452 - 5454

78
[ 69-78-3 ]
[Na(18-crown-6)]2[Fe2(μ-S)2(NO)4] [ No CAS ]
[ 1335311-62-0 ]

Reference： [1]Inorganic Chemistry,2011,vol. 50,p. 10417 - 10431

79
[ 69-78-3 ]
antibody SIP(F₈) [ No CAS ]
SIP(F₈)-Ellman's conjugate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 941 - 944

80
[ 69-78-3 ]
histone H₃ (K₄C, K₇₉C, C₁₁₀A) [ No CAS ]
histone H₃ (4,79-[S-(3-carboxy-4-nitrophenylthio)cysteine]2, 110-alanine) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 1835 - 1839

81
[ 69-78-3 ]
histone H₃ (K₉C, C₁₁₀A) [ No CAS ]
histone H₃ (9-[S-(3-carboxy-4-nitrophenylthio)cysteine], 110-alanine) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 1835 - 1839

82
[ 69-78-3 ]
histone H₃ (S₁₀C, C₁₁₀A) [ No CAS ]
histone H₃ (10-[S-(3-carboxy-4-nitrophenylthio)cysteine], 110-alanine) [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 1835 - 1839

83
[ 67-56-1 ]
[ 69-78-3 ]
[ 115215-73-1 ]

Yield	Reaction Conditions	Operation in experiment
55%	With thionyl chloride; at 0℃; for 19h;Reflux;	General procedure: In an ice bath, SOCl2 (8 mL) was slowly added dropwise to anhydrous methanol (30 mL) at 0 C. After 30 min, 5,5'-disulfanediylbis(2-nitrobenzoic acid) (2.5 g, 6.3 mmol) was added, and the resulting mixture was further stirred at 0 C for 1h. After stirring at room temperature for 12h, the solution was then heated at reflux for 6h and cooled to room temperature. The resulting precipitate was filtered and dried to provide 11 as a yellow solid.

Reference： [1]ARKIVOC,2012,vol. 2012,p. 245 - 252
[2]Chinese Chemical Letters,2017,vol. 28,p. 1248 - 1251
[3]Angewandte Chemie - International Edition,2019,vol. 58,p. 1950 - 1954
Angew. Chem.,2019,vol. 131,p. 1970 - 1974,5

84
[ 69-78-3 ]
[ 951666-94-7 ]

Reference： [1]ARKIVOC,2012,vol. 2012,p. 245 - 252

85
[ 69-78-3 ]
[ 6674-22-2 ]
[ 1379592-24-1 ]

Reference： [1]ARKIVOC,2012,vol. 2012,p. 245 - 252

86
[ 69-78-3 ]
[ 85-61-0 ]
C₂₈H₃₈N₈O₂₀P₃S₂^(1-) [ No CAS ]
[ 77874-90-9 ]

Reference： [1]ChemBioChem,2011,vol. 12,p. 2289 - 2293

87
[ 69-78-3 ]
[ 1228577-53-4 ]
[ 1385789-88-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 5278 - 5288

88
[ 69-78-3 ]
5-thio-2-nitrobenzoic acid [ No CAS ]

Reference： [1]Chemical Research in Toxicology,2012,vol. 25,p. 1502 - 1511

89
[ 69-78-3 ]
Vibrio cholerae transcription activator ToxR reduced form [ No CAS ]
Vibrio cholerae transcription activator ToxR reduced form activated with 5,5'-dithiobis(2-nitrobenzoic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. buffer; at 20℃; for 0.5h;pH 7;	The attachment of 6 to reduced cysteines in proteins was tested on the Vibrio cholerae transcription activator ToxR. The purified protein was dialyzed extensively against 50 mM Tris buffer (pH 7.6) before applying 1 ml of the protein solution (2 mg/ml) to a PD MidiTrap G-25 Column (Life Technologies) equilibrated with the same buffer. The protein was eluted from the column with 1.5 ml of the Tris buffer. The fractions containing protein were pooled and DTNB (dissolved in Tris buffer and adjusted to approximately pH 7 with 1 M Tris buffer pH 8.0) was added to a final concentration of 10 mM. The resulting light yellow mixture was incubated at room temperature for 30 min prior to being applied to the newly equilibrated column. Again the protein solution was eluted with 1.5 ml of the Tris buffer, the protein fractions united and once more applied to the equilibrated column. This step was repeated twice to remove the excess DTNB, which could be monitored easily due to the yellowish color of the DTNB. In a next step, 6 dissolved in the same Tris buffer (colorless) was added to the protein solution in a final concentration of 5 mM and the resulting light yellow mixture was incubated at room temperature for another 30 min before being applied to the equilibrated column. Again the protein solution was eluted with 1.5 ml of the Tris buffer and the combined protein fractions once more applied to the column. This step was repeated twice. In parallel another ToxR sample of the same concentration but pre-treated with DTT was tagged. For this purpose DTT dissolved in the same Tris buffer was added to the protein solution to a final concentration of 10 mM. This mixture was incubated at room temperature for approximately 45 min prior to being applied to a PD MidiTrap G-25 Column. All subsequent steps were then carried out in the exact same way as described above for the untreated ToxR sample. For the NMR

Reference： [1]Carbohydrate Research,2012,vol. 361,p. 100 - 104,5

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 69-78-3 ] {[proInfo.proName]}

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[ 69-78-3 ] Synthesis Path-Upstream 1~5

[ 69-78-3 ] Synthesis Path-Downstream 1~89

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