174658-22-1

Basic information

• Product Name: Benzonitrile, 4-amino-3-mercapto- (9CI)
• Synonyms: Benzonitrile, 4-amino-3-mercapto- (9CI);4-AMINO-3-SULFANYLBENZONITRILE;4-Amino-3-mercaptobenzonitrile
• CAS NO: 174658-22-1
• Molecular Formula: C₇H₆N₂S
• Molecular Weight: 150.20094
• Product Categories: AMINEPRIMARY
• Mol File: 174658-22-1.mol

Chemical Properties

• Appearance: /
• Density: 1.27
• CAS DataBase Reference: Benzonitrile, 4-amino-3-mercapto- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-amino-3-mercapto- (9CI)(174658-22-1)
• EPA Substance Registry System: Benzonitrile, 4-amino-3-mercapto- (9CI)(174658-22-1)

Safety Data

• Hazardous Substances Data: 174658-22-1(Hazardous Substances Data)

Upstream product

• 58249-61-9 6-cyano benzothiazole 
• 19759-66-1 2-amino-6-cyanobenzthiazole 
• 873-74-5 4-Aminobenzonitrile 

Downstream Products

• 402767-63-9 2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-thiophenecarbonitrile 
• 402767-61-7 2-[4-(6-cyanobenzothiazol-2-yl)phenyl]-5-furancarbonitrile 
• 77333-68-7 2-phenylbenzo[d]thiazole-6-carbonitrile 
• 67349-25-1 6-cyano-2-(4-cyanophenyl)benzothiazole 
• 1221688-94-3 6-cyano-2-(4-nitrophenyl)benzothiazole 
• 1397706-39-6 C₁₈H₁₇N₃S 
• 80945-83-1 2-chloro-1,3-benzothiazole-6-carbonitrile 
• 1333242-91-3 5-(3-(6-cyanobenzo[d]thiazol-2-yl)phenyl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 618913-75-0 2-(4-carboxyphenyl)-5-(6-cyanobenzothiazol-2-yl)thiophene 
• 618913-74-9 2-(4-carboxyphenyl)-5-(6-cyanobenzothiazol-2-yl)furan 

Relevant articles and documents

Green synthesis and biological evaluation of 6-substituted-2-(2-hydroxy/methoxy phenyl)benzothiazole derivatives as potential antioxidant, antibacterial and antitumor agents

We present a new efficient green synthetic protocol for introduction of substituents to the C-6 position of 2-arylbenzothiazole nuclei. Newly synthesized compounds were designed to study the influence of the hydroxy and methoxy groups on the 2-arylbenzothiazole scaffold, as well as the influence of the type of substituents placed on the C-6 position of benzothiazole moiety on biological activity, including antibacterial, antitumor and antioxidant activity. Modest activity was observed against the tested Gram-positive and Gram-negative bacterial strains for only amidino derivatives 5d and 6d. The tested compounds exhibited moderate to strong antiproliferative activity towards the tumor cell lines tested. The SAR study revealed that the introduction of substituents into the benzene ring of the benzothiazole nuclei is essential for antiproliferative activity, while introduction of the hydroxy group into the 2-aryl moiety of the 2-arybenzothiazole scaffold significantly improved selectivity against tumor cell lines. The observed results revealed several novel 6-substituted-2-arylbenzothiazole compounds, 5b, 5c, 5f and 6f, with strong and selective antiproliferative activity towards HeLa cells in micro and submicromolar concentrations, with the most selective compounds being 6-ammonium-2-(2-hydroxy/methoxyphenyl)benzothiazoles 5f and 6f. The compound 5f bearing the hydroxy group on the 2-arylbenzothiazole core showed the most promising antioxidative activity evaluated by DPPH, ABTS and FRAP in vitro assays. The presence of the amino protonated group attached at the benzothiazole moiety was essential for the antiproliferative and antioxidant activity observed, exerted through a change in the levels of the reactive oxygen species-modulated HIF-1 protein.

Novel amidino substituted 2-phenylbenzothiazoles: Synthesis, antitumor evaluation in vitro and acute toxicity testing in vivo

The efficient synthesis of new bis-substituted nitro-amidino, amino-amidino (10a, 10b-13a, 13b) and previously prepared diamidino 2-phenyl-benzothiazoles (9a, 9b) is described. The compounds 11a and 11b were prepared by recently developed methodology of the key precursors in zwitterionic form 8a and 8b with 4-nitrobenzoylchloride in a very good yield (70%). All compounds except diamidino-substituted 2-phenylbenzothiazole 9a show exceptionally prominent tumor cell-growth inhibitory activity and cytotoxicity, whereby the special selectivity of amino-amidine 2-phenylbenzothiazole 12a towards MCF-7 and H 460 cells makes this compound a prospective lead compound that should be further evaluated in animal models. All in vivo tested compounds (12a, 12b, 13a and 13b) are absorbed from mice gastrointestinal system. LD50 are between 67.33 and 696.2 mg/kg body weight (OECD/EPA toxicity categories 2-3).

Synthesis and antifungal activity of novel thiazole-containing triazole antifungals. II. Optically active ER-30346 and its derivatives

A series of novel thiazole-containing triazole antifungals was synthesized and evaluated for antifungal activity against a variety of clinically isolated pathogenic fungi in vitro and against systemic candidosis in vivo. These compounds showed potent antifungal activities in vitro and in vivo. In particular, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4- difluorophenyl)-1-(1H-1,2,4-triazol-l-yl)-2-butanol (12g; ER-30346) showed potent and well-balanced in vitro activities and potent in vivo efficacy, and had a good safety profile.