Indole, first isolated in 1866, has the molecular formula C8H7N, and it is commonly synthesized from phenylhydrazine and pyruvic acid, 771-51-7, formula is C10H8N2, Name is 2-(1H-Indol-3-yl)acetonitrile. although several other procedures have been discovered.Indole is a colourless solid having a pleasant fragrance in highly dilute solutions. It melts at 52.5° C (126.5° F). Synthetic Route of 771-51-7.
Mondal, Pritam;Rajapakse, Shanuk;Wijeratne, Gayan B. research published 《 Following Nature’s Footprint: Mimicking the High-Valent Heme-Oxo Mediated Indole Monooxygenation Reaction Landscape of Heme Enzymes》, the research content is summarized as follows. Pathways for direct conversion of indoles to oxindoles have accumulated considerable interest in recent years due to their significance in the clear comprehension of various pathogenic processes in humans and the multipotent therapeutic value of oxindole pharmacophores. Heme enzymes are predominantly responsible for this conversion in biol. and are thought to proceed with a compound-I active oxidant. These heme-enzyme-mediated indole monooxygenation pathways are rapidly emerging therapeutic targets; however, a clear mechanistic understanding is still lacking. Addnl., such knowledge holds promise in the rational design of highly specific indole monooxygenation synthetic protocols that are also cost-effective and environmentally benign. We herein report the first examples of synthetic compound-I and activated compound-II species that can effectively monooxygenate a diverse array of indoles with varied electronic and steric properties to exclusively produce the corresponding 2-oxindole products in good to excellent yields. Rigorous kinetic, thermodn., and mechanistic interrogations clearly illustrate an initial rate-limiting epoxidation step that takes place between the heme oxidant and indole substrate, and the resulting indole epoxide intermediate undergoes rearrangement driven by a 2,3-hydride shift on indole ring to ultimately produce 2-oxindole. The complete elucidation of the indole monooxygenation mechanism of these synthetic heme models will help reveal crucial insights into analogous biol. systems, directly reinforcing drug design attempts targeting those heme enzymes. Moreover, these bioinspired model compounds are promising candidates for the future development of better synthetic protocols for the selective, efficient, and sustainable generation of 2-oxindole motifs, which are already known for a plethora of pharmacol. benefits.
Synthetic Route of 771-51-7, 3-Indoleacetonitrile is a plant growth activator, which promotes callus growth and shoot formation in tobacco callus.
3-Indoleacetonitrile (Indolylacetonitrile) is a light-induced auxin-inhibitory substance that is isolated from light-grown cabbage (Brassica olearea L.) shoots. It inhibits the biofilm formation of both E. coli O157:H7 and P. aeruginosa without affecting its growth.
3-Indoleacetonitrile, also known as 3-(cyanomethyl)indole or IAN, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 3-Indoleacetonitrile exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, 3-indoleacetonitrile is primarily located in the mitochondria. 3-Indoleacetonitrile participates in a number of enzymatic reactions. In particular, 3-indoleacetonitrile can be biosynthesized from acetonitrile. 3-Indoleacetonitrile is also a parent compound for other transformation products, including but not limited to, cys(ian)-gly, gammaglucys(ian), and L-cys(ian). Outside of the human body, 3-indoleacetonitrile can be found in a number of food items such as cloudberry, japanese persimmon, horned melon, and evergreen huckleberry. This makes 3-indoleacetonitrile a potential biomarker for the consumption of these food products.
Indole-3-acetonitrile is a nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group. It has a role as an auxin, a plant hormone, a plant metabolite and a human xenobiotic metabolite. It is a nitrile and a member of indoles. It derives from an acetonitrile., 771-51-7.
Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles