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5-Chloroindole-3-acetonitrile is a chemical compound with the molecular formula C10H7ClN2, belonging to the indole class of heterocyclic organic compounds. It features a chlorine atom on the fifth carbon of the indole ring and is recognized for its role in the synthesis of pharmaceuticals and agrochemicals, as well as its potential biological activities, including antitumor and antiviral properties. This makes 5-Chloroindole-3-acetonitrile a significant molecule in medicinal chemistry and pharmaceutical research.

81630-83-3

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81630-83-3 Usage

Uses

Used in Pharmaceutical Industry:
5-Chloroindole-3-acetonitrile is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique chemical structure and reactivity, contributing to the development of new drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
5-Chloroindole-3-acetonitrile is also utilized in the synthesis of agrochemicals, serving as a building block for the creation of new pesticides or other agricultural chemicals, thereby enhancing crop protection and yield.
Used in Research and Development:
5-Chloroindole-3-acetonitrile is employed as a research tool in the exploration of new drug candidates, leveraging its potential biological activities to identify and optimize compounds with therapeutic potential.
Used in Antitumor Applications:
5-Chloroindole-3-acetonitrile is studied for its potential antitumor properties, with the aim of developing it into a chemotherapeutic agent or contributing to the synthesis of compounds that can inhibit tumor growth and progression.
Used in Antiviral Applications:
5-Chloroindole-3-acetonitrile is also investigated for its antiviral properties, with research focusing on its ability to inhibit viral replication or infectivity, potentially leading to the development of new antiviral medications.

Check Digit Verification of cas no

The CAS Registry Mumber 81630-83-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,6,3 and 0 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 81630-83:
(7*8)+(6*1)+(5*6)+(4*3)+(3*0)+(2*8)+(1*3)=123
123 % 10 = 3
So 81630-83-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H7ClN2/c11-8-1-2-10-9(5-8)7(3-4-12)6-13-10/h1-2,5-6,13H,3H2

81630-83-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(5-chloro-1H-indol-3-yl)acetonitrile

1.2 Other means of identification

Product number -
Other names 5-Chlor-3-cyanomethylindol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:81630-83-3 SDS

81630-83-3Relevant academic research and scientific papers

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

Bojarski, Andrzej J.,Bugno, Ryszard,Cie?lik, Paulina,Duszyńska, Beata,Handzlik, Jadwiga,Hogendorf, Adam S.,Hogendorf, Agata,Kaczorowska, Katarzyna,Kurczab, Rafa?,Latacz, Gniewomir,Lenda, Tomasz,Sata?a, Grzegorz,Staroń, Jakub,Szewczyk, Bernadeta

, (2021/08/17)

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst

Egami, Hiromichi,Hotta, Ryo,Otsubo, Minami,Rouno, Taiki,Niwa, Tomoki,Yamashita, Kenji,Hamashima, Yoshitaka

supporting information, p. 5656 - 5660 (2020/07/14)

Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water is essential, and its possible role is discussed.

Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)

See, Cheng Shang,Kitagawa, Mayumi,Liao, Pei-Ju,Lee, Kyung Hee,Wong, Jasmine,Lee, Sang Hyun,Dymock, Brian W.

, p. 344 - 367 (2018/07/25)

Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.

SELECTIVE ANTI-CANCER COMPOUNDS

-

Page/Page column 82-83, (2017/01/31)

A compound of formula I, wherein the compound of formula I has the structure: wherein R1 to R5, Y, L, Z and X1 to X7 have meanings given in the description, said compounds having utility in the treatment of hyperproliferative disease.

Use of derivatives of indoles for the treatment of cancer

-

Page/Page column 51; 52, (2016/01/09)

The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.

Use of derivatives of indoles for the treatment of cancer

-

, (2011/01/12)

The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.

Methods of reducing serum glucose and triglyceride levels and for inhibiting angiogenesis using substituted indolealkanoic acids

-

, (2008/06/13)

Disclosed are methods of reducing serum glucose and triglyceride levels and for inhibiting angiogenesis, the methods comprising administration of substituted indolealkanoic acids to patients in need of such treatment. Also disclosed are such compounds use

Compositions containing a substituted indolealkanoic acid and an angiotensin converting enzyme inhibitor

-

, (2008/06/13)

Disclosed are methods of reducing serum glucose and triglyceride levels and for inhibiting angiogenesis, the methods comprising administration of substituted indolealkanoic acids to patients in need of such treatment. Also disclosed are such compounds use

Methods for reducing uric acid levels

-

, (2008/06/13)

Disclosed are methods of reducing serum uric acid levels, the methods comprising administration of substituted indolealkanoic acids to patients in need of such treatment. Also disclosed are such compounds useful in the treatment of gout and related diseas

Substituted indolealkanoic acids

-

, (2008/06/13)

Disclosed are substituted indolealkanoic acids useful in the treatment of chronic complications arising from diabetes mellitus. Also disclosed are pharmaceutical compositions containing the compounds and methods of treatment employing the compounds, as we

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