21909-52-4

Usage

Uses

Used in Pharmaceutical Industry:
(5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential biological activities.
Used in Medicinal Research:
(5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE is used as a research molecule for its anti-inflammatory and neuroprotective effects, contributing to the development of new therapeutic agents.
Used in Plant Growth Regulation:
(5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE is used as a synthetic auxin in the field of plant growth regulators, aiding in the control and enhancement of plant growth.
Used in Chemical Research:
(5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE is used as a building block for the synthesis of other biologically active compounds, expanding its applications in chemical research and development.

InChI:InChI=1/C11H13N3O/c1-7-2-3-10-9(4-7)8(6-13-10)5-11(15)14-12/h2-4,6,13H,5,12H2,1H3,(H,14,15)

Upstream product

• 1337870-84-4 (5-methyl-indol-3-yl)-acetic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their protective activity against oxidative stress

A small library of 2-[(1H-indol-3-yl)methyl]-5-(alkylthio)-1,3,4-oxadiazoles was prepared, starting from indole-3-acetic acid methyl ester and its 5-methyl-substituted derivative. The synthetic route involved the formation of intermediate hydrazides, their condensation with carbon disulfide, and intramolecular cyclization to corresponding 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones. The latter were then S-alkylated, and in case of ester derivatives, they were further hydrolyzed into corresponding carboxylic acids. All 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their S-alkylated derivatives were then screened for their protective effects in vitro and in vivo. Methyl substitution on the indole ring and propyl, butyl, or benzyl substitution on sulfhydryl group-possessing compounds were revealed to protect Friedreich's ataxia fibroblasts against the effects of glutathione depletion induced by the γ-glutamylcysteine synthetase inhibitor, buthionine sulfoximine. Two of the active compounds also reproducibly increased the survival of Caenorhabditis elegans exposed to juglone-induced oxidative stress.