85452-79-5

Basic information

• Product Name: (Z)-3-(1H-indol-3-yl)acrylonitrile
• Synonyms: (Z)-3-(1H-indol-3-yl)acrylonitrile
• CAS NO: 85452-79-5
• Molecular Formula: C₁₁H₈N₂
• Molecular Weight: 168.19462
• EINECS: -0
• Mol File: 85452-79-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (Z)-3-(1H-indol-3-yl)acrylonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-(1H-indol-3-yl)acrylonitrile(85452-79-5)
• EPA Substance Registry System: (Z)-3-(1H-indol-3-yl)acrylonitrile(85452-79-5)

Safety Data

• Hazardous Substances Data: 85452-79-5(Hazardous Substances Data)

Usage

General Description

"(Z)-3-(1H-indol-3-yl)acrylonitrile" is a chemical compound belonging to the class of organic compounds known as indoles. Indoles are compounds containing the indole moiety, a bicyclic heterocycle consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (Z)-3-(1H-indol-3-yl)acrylonitrile is composed of an acrylonitrile group (a carbon-carbon double bond with a cyano group) attached to the 3-position of an indole ring via a double bond. As a noteworthy detail about this chemical, its formed by the combination of two other chemicals. Its potential applications and properties are typically determined by its specific structure, though they may not be widely established in the literature.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 372-09-8 cyanoacetic acid 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 20356-45-0 3-(1H-indol-3-yl)-3-oxo-propionitrile 
• 6286-56-2 3-<(2-cyano-2-ethoxycarbonyl)ethenyl>indole 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 120-72-9 indole 
• 107-13-1 acrylonitrile 

Downstream Products

• 4414-76-0 1H-indole-3-propiononitrile 

Relevant articles and documents

Structural Diversification of Hapalindole and Fischerindole Natural Products via Cascade Biocatalysis

Hapalindoles and related compounds (ambiguines, fischerindoles, welwitindolinones) are a diverse class of indole alkaloid natural products. They are typically isolated from the Stigonematales order of cyanobacteria and possess a broad scope of biological activities. Recently the biosynthetic pathway for assembly of these metabolites has been elucidated. In order to generate the core ring system, l-tryptophan is converted into the cis-indole isonitrile subunit before being prenylated with geranyl pyrophosphate at the C-3 position. A class of cyclases (Stig) catalyzes a three-step process, including a Cope rearrangement, 6-exo-trig cyclization, and electrophilic aromatic substitution, to create a polycyclic core. The formation of the initial alkaloid is followed by diverse late-stage tailoring reactions mediated by additional biosynthetic enzymes to give rise to a wide array of structural variations observed in this compound class. Herein, we demonstrate the versatility and utility of the Fam prenyltransferase and Stig cyclases toward the core structural diversification of this family of indole alkaloids. Through the synthesis of cis-indole isonitrile subunit derivatives, and with the aid of protein engineering and computational analysis, we have employed cascade biocatalysis to generate a range of derivatives and gained insights into the basis for substrate flexibility in this system.

Palladium-catalyzed intermolecular C3 alkenylation of indoles using oxygen as the oxidant

A general and efficient palladium-catalyzed intermolecular direct C3 alkenylation of indoles using oxygen as the oxidant has been developed. The reaction is of complete regio- and stereoselectivity. All products are E-isomers at the C3-position, and no Z-

Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators

Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active area of research in drug development. Recently, our group has shown that tryptophan 2,3-dioxygenase (TDO), an unrelated hepatic enzyme also catalyzing the first step of tryptophan degradation, is also expressed in many tumors and that this expression prevents tumor rejection by locally depleting tryptophan. Herein, we report a structure-activity study on a series of 3-(2-(pyridyl)ethenyl)indoles. More than 70 novel derivatives were synthesized, and their TDO inhibitory potency was evaluated. The rationalization of the structure-activity relationships (SARs) revealed essential features to attain high TDO inhibition and notably a dense H-bond network mainly involving His55 and Thr254 residues. Our study led to the identification of a very promising compound (58) displaying good TDO inhibition (Ki = 5.5 μM), high selectivity, and good oral bioavailability. Indeed, 58 was chosen for preclinical evaluation.