154422-23-8

Usage

Molecular weight

223.3

Structure

Indole ring with a carboxylic acid group (-COOH) at position 2, a methylthio group (-SCH3) at position 3, and an ethyl ester group (-COOCH2CH3) attached to the carboxylic acid.

Appearance

Pale yellow solid

Solubility

Slightly soluble in water, soluble in organic solvents such as ethanol, methanol, and chloroform

Biological activity

Has potential antifungal and antiproliferative properties

Uses

Building block in organic synthesis and pharmaceutical research, starting material for the synthesis of various pharmaceuticals and agrochemicals.

Upstream product

• 1440957-30-1 (2-carboethoxyindol-3-yl)dimethylsulfonium perchlorate 
• 142-84-7 di-n-propylamine 

Relevant academic research and scientific papers

A practical regioselective synthesis of alkylthio- or arylthioindoles without the use of smelly compounds such as thiols

A convenient method for the synthesis of 3-methylthioindoles has been established which does not use smelly compounds such as thiol derivatives. The method, which introduces an alkyl- or arylthio-group into the C3-position of the indole skeleton, was extended to the direct introduction of a methylthio or bromo group at the C2-position using 3-methylthioindoles. No dimerization occurred, and the reaction mechanism was confirmed. The products have the partial structure of potent anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) bromomethylthioindoles (MC 5-8) isolated from marine algae. Furthermore, this reaction could be applied to the synthesis of 3,3-diindolyl thioether which is a core structure of Echinosulfone A.

Fischer indolization of variously ortho-substituted phenylhydrazones (Fischer indolization and its related compounds. XXV)

Various kinds of ethyl pyruvate 2-(2-substituted phenyl)hydrazones (1) were subjected to Fischer indolization with acid catalysts. All the phenylhydrazones gave corresponding normal 7-substituted indoles (2). In addition, phenylhydrazones whose ortho-substituent is electron-donative or has a central atom with an unshared electron pair tended to give the 4- or 5- substituted indole (3), which was produced by migration of the ortho- substituent during cyclization, whereas those whose ortho-substituent is electron-attractive tended to give little or no such abnormal product. The kind of acid catalyst used had some effect on the yield ratio of products but not on the kind of products.