116757-24-5

Basic information

• Product Name: 1H-Indole-2-carboxylic acid, 3-(phenylthio)-, methyl ester
• CAS NO: 116757-24-5
• Molecular Formula: C16H13NO2S
• Molecular Weight: 283.351
• Mol File: 116757-24-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1H-Indole-2-carboxylic acid, 3-(phenylthio)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-2-carboxylic acid, 3-(phenylthio)-, methyl ester(116757-24-5)
• EPA Substance Registry System: 1H-Indole-2-carboxylic acid, 3-(phenylthio)-, methyl ester(116757-24-5)

Safety Data

• Hazardous Substances Data: 116757-24-5(Hazardous Substances Data)

Usage

Molecular Structure

1H-Indole-2-carboxylic acid, 3-(phenylthio)-, methyl ester is a chemical compound with a structure that features an indole ring system with a carboxylic acid group at the 2-position and a phenylthio group at the 3-position, and a methyl ester group attached to the carboxylic acid.

Derivation

This compound is derived from the indole class of organic compounds, specifically as a methyl ester of 1H-indole-2-carboxylic acid with a phenylthio group attached at the 3 position.

Applications

1H-Indole-2-carboxylic acid, 3-(phenylthio)-, methyl ester has potential applications in organic synthesis and pharmaceutical research, as indole derivatives are known for their diverse biological activities. It is commonly used in the synthesis of various pharmaceuticals and agrochemicals.

Chemical Reactivity

This compound has a unique chemical structure and reactivity due to the presence of the indole ring system, carboxylic acid, phenylthio group, and methyl ester group.

Safety Precautions

It is important to handle and use 1H-Indole-2-carboxylic acid, 3-(phenylthio)-, methyl ester with caution, as it may have toxic or hazardous properties if not handled properly.

Upstream product

• 116757-25-6 3-(phenylthio)-1H-indole-2-carboxylic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 882-33-7 diphenyldisulfane 
• 1477-50-5 Indole-2-carboxylic acid 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 14204-24-1 N-(phenylthio)succinimide 

Downstream Products

• 116757-25-6 3-(phenylthio)-1H-indole-2-carboxylic acid 
• 441800-90-4 Methyl 3-(phenylsulfonyl)-1H-indole-2-carboxylate 
• 1202-04-6 indole-2-carboxylic acid methyl ester 

Relevant articles and documents

Iodine-promoted selective 3-selanylation and 3-sulfenylation of indoles with dichalcogenides under mild conditions

A simple method was developed for the synthesis of 3-chalcogen indoles via iodine-promoted direct 3-selanyl- and 3-sulfenylation of indoles with dichalcogenides. The reaction was carried out smoothly in EtOH under air at room temperature, selectively givi

New arylthioindoles: Potent inhibitors of tubulin polymerization. 2. Structure-activity relationships and molecular modeling studies

Arylthioindoles (ATIs) that possess a 3-methoxyphenylthio or a 3,5-dimethoxyphenylthio moiety at position 2 of the indole ring were effective tubulin assembly inhibitors, but weak inhibitors of MCF-7 cell growth. ATIs bearing a 3-(3,4,5-trimethoxyphenyl)thio moiety were potent tubulin polymerization inhibitors, with IC50s in the 2.0 (35) to 4.5 (37) μM range. They also inhibited MCF-7 cell growth at nanomolar concentrations. The 3,4,5-trimethoxy substituted ATIs showed potencies comparable to those of the reference compounds colchicine and combretastatin A-4 in both tubulin assembly and cell growth inhibition assays. Dynamics simulation studies correlate well with the observed experimental data. Furthermore, from careful analysis of the biological and in silico data, we can now hypothesize a basic pharmacophore for this class of compounds.

Arylthioindoles, potent inhibitors of tubulin polymerization

Several arylthioindoles had excellent activity as inhibitors both of tubulin polymerization and of the growth of MCF-7 human breast carcinoma cells. Methyl 3-[(3,4,5-tri-methoxypheny)thio]-5-methoxy-1H-indole-2-carboxylate (21), the most potent derivative