894231-58-4

Basic information

• Product Name: 2-(1H-indole-3-carbonyl)-N-(benzyl)hydrazinecarbothioamide
• Synonyms: 2-(1H-indole-3-carbonyl)-N-(benzyl)hydrazinecarbothioamide
• CAS NO: 894231-58-4
• Molecular Weight: 324.406
• Mol File: 894231-58-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(1H-indole-3-carbonyl)-N-(benzyl)hydrazinecarbothioamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1H-indole-3-carbonyl)-N-(benzyl)hydrazinecarbothioamide(894231-58-4)
• EPA Substance Registry System: 2-(1H-indole-3-carbonyl)-N-(benzyl)hydrazinecarbothioamide(894231-58-4)

Safety Data

• Hazardous Substances Data: 894231-58-4(Hazardous Substances Data)

Upstream product

• 771-50-6 1H-indole-3-carboxylic acid 
• 776-41-0 indole-3-carboxylic acid ethyl ester 
• 15317-58-5 1H-indole-3-carboxylic acid hydrazide 
• 622-78-6 Benzyl isothiocyanate 

Downstream Products

• 1396743-72-8 C₁₇H₁₄N₄S 

Relevant articles and documents

Synthesis and evaluation of 5-(1H-indol-3-yl)-N-aryl-1,3,4-oxadiazol-2-amines as Bcl-2 inhibitory anticancer agents

A series of 5-(1H-indol-3-yl)-N-aryl-1,3,4-oxadiazol-2-amines 8a–j has been designed, synthesized and tested in vitro as potential pro-apoptotic Bcl-2-inhibitory anticancer agents based on our previous lead compound 8a. Synthesis of the target compounds was readily accomplished through a cyclisation reaction between indole-3-carboxylic acid hydrazide (5) and substituted isothiocyanates 6a–j, followed by oxidative cyclodesulfurization of the corresponding thiosemicarbazide 7a–j using 1,3-dibromo-5,5-dimethylhydantoin. Active compounds of the series 8a–j were found to have sub-micromolar IC50 values selectively in Bcl-2 expressing human cancer cell lines; notably the 2-nitrophenyl analogue 8a was found to exhibit potent activity, and compounds 8a and 8e possessed comparable Bcl-2 binding affinity (ELISA assay) to the established natural product-based Bcl-2 inhibitor, gossypol. Molecular modeling studies helped to further rationalise anti-apoptotic Bcl-2 binding, and identified compounds 8a and 8e as candidates for further development as Bcl-2 inhibitory anticancer agents.

A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles as potent cytotoxic agents

A series of 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles 6a-v were prepared and studied for their anticancer activity against selected human cancer cell lines. The reaction of indolylhydrazides 3a-h with a variety of aryl isothiocyanates 4 afforded the key intermediate thiosemicarbazides 5a-v, which upon treatment with acetyl chloride produced the 2-arylamino-5-(indolyl)-1,3,4- thiadiazoles 6a-v in good yields. Most of the synthesized compounds showed selective cytotoxicity towards human breast cancer cell line (MDA-MB-231). Of the synthesized 2-arylamino-5-(indolyl)-1,3,4-thiadiazoles, compound 6f is the most potent towards tested cancer cell lines (IC50 = 0.15-1.18 μM).