220269-39-6

Basic information

• Product Name: ethyl 3-amino-2-(3-bromobenzoyl)-6-chloro-1H-indole-1-carboxylate
• CAS NO: 220269-39-6
• Molecular Weight: 421.678
• Mol File: 220269-39-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl 3-amino-2-(3-bromobenzoyl)-6-chloro-1H-indole-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3-amino-2-(3-bromobenzoyl)-6-chloro-1H-indole-1-carboxylate(220269-39-6)
• EPA Substance Registry System: ethyl 3-amino-2-(3-bromobenzoyl)-6-chloro-1H-indole-1-carboxylate(220269-39-6)

Safety Data

• Hazardous Substances Data: 220269-39-6(Hazardous Substances Data)

Upstream product

• 220269-23-8 4-chloro-2-[(ethoxycarbonyl)amino]benzonitrile 
• 18523-22-3 2,3'-dibromoacetophenone 
• 38487-86-4 2-amino-4-chlorobenzonitrile 

Relevant articles and documents

Synthesis, biological evaluation, and molecular docking investigation of 3-amidoindoles as potent tubulin polymerization inhibitors

A series of novel 3-amidoindole derivatives possessing 3,4,5-trimethoxylphenyl groups were synthesized and evaluated for their antiproliferative and tubulin polymerization inhibitory activities. Some of them demonstrated moderate to potent activities in vitro against six cancer cell lines including MCF-7, MDA-MB-231, BT549, T47D, MDA-MB-468, and HS578T. The most active compound 27 inhibited the growth of T47D, BT549, and MDA-MB-231 cell lines with IC50 values at 0.04, 3.17, and 6.43 μM, respectively. Moreover, the flow cytometric analysis clearly revealed that compound 27 significantly inhibited growth of breast cancer cells through arresting cell cycle in G2/M phase via a concentration-dependent manner. In addition, the compound also exhibited the most potent anti-tubulin activity with IC50 values of 9.5 μM, which was remarkable, compared to CA-4. Furthermore, molecular docking analysis demonstrated the interaction of the compound 27 at the colchicine-binding site of tubulin. These preliminary results suggest that compound 27 is a very promising tubulin-binding agent and is worthy of further investigation aiming to the development of new potential anticancer agents.

Substituted indole compounds as anti-inflammatory and analgesic agents

This invention provides a compound of the following formula: or the pharmaceutically acceptable salts thereof wherein R1is H or C1-4alkyl; R2is C(═L′)R3or So2R4; Y is a direct bond or C1-4alkylene; L and L′ are independently oxygen or sulfur; Q is selected from the following: C1-6alkyl, halo-substituted C1-4alkyl, optionally substituted C3-7cycloalkyl, optionally substituted phenyl or naphthyl, optionally substituted5or6-membered monocyclic aromatic group; R3is —OR6, —NR7R8, N(OR1)R7or a group of formula: Z is a direct bond, O, S or NR5; R4is C1-6alkyl, halo-substituted C1-4alkyl, optionally substituted phenyl or naphthyl; R5is C1-4alkyl or halo-substituted C1-4alkyl; R6is C1-4alkyl C3-7cycloalkyl, C1-4alkyl-C3-7cycloalkyl, halo-substituted C1-4alkyl, optionally substituted C1-4alkyl-phenyl or phenyl; R7and R8are each selected from the following: H, optionally substituted C1-6alkyl, optionally substituted C3-7cycloalkyl, optionally substituted C1-4alkyl-C3-7cycloalkyl, and optionally substituted C1-4alkyl-phenyl or phenyl; X is each selected from halo, C1-4alkyl, halo-substituted C1-4alkyl, OH, C1-4alkoxy, halo-substituted C1-4alkoxy, C1-4alkylthio, NO2, NH2, di-(C1-4alkyl)amino and CN; n is 0, 1, 2 or 3; and r is 1, 2 or 3. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens.