24526-89-4

Basic information

• Product Name: 4-(4-CHLOROANILINO)-2H-CHROMEN-2-ONE
• Synonyms: 4-(4-CHLOROANILINO)-2H-CHROMEN-2-ONE
• CAS NO: 24526-89-4
• Molecular Formula: C₁₅H₁₀ClNO₂
• Molecular Weight: 271.7
• Mol File: 24526-89-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 299-301°C
• Boiling Point: 451°Cat760mmHg
• Flash Point: 226.5°C
• Appearance: /
• Density: 1.415g/cm³
• Vapor Pressure: 2.53E-08mmHg at 25°C
• Refractive Index: 1.696
• PKA: -1.12±0.20(Predicted)
• CAS DataBase Reference: 4-(4-CHLOROANILINO)-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-CHLOROANILINO)-2H-CHROMEN-2-ONE(24526-89-4)
• EPA Substance Registry System: 4-(4-CHLOROANILINO)-2H-CHROMEN-2-ONE(24526-89-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 24526-89-4(Hazardous Substances Data)

Usage

General Description

4-(4-Chloroanilino)-2H-chromen-2-one, also known as ICG-001, is a synthetic small molecule compound that has been studied for its potential anticancer and anti-inflammatory properties. It belongs to the class of chromen-2-ones, which are known to have diverse pharmacological activities. 4-(4-Chloroanilino)-2H-chromen-2-one has been shown to inhibit the Wnt/β-catenin signaling pathway, which plays a critical role in regulating cell proliferation and differentiation. This inhibition has been found to have potential therapeutic implications in the treatment of cancers and inflammatory diseases. Additionally, this compound has been investigated for its role in promoting the differentiation of stem cells and repairing tissue damage. Overall, 4-(4-Chloroanilino)-2H-chromen-2-one shows promise as a potential candidate for the development of novel therapeutic agents for various diseases.

InChI:InChI=1/C15H10ClNO2/c16-10-5-7-11(8-6-10)17-13-9-15(18)19-14-4-2-1-3-12(13)14/h1-9,17H

Upstream product

• 106-47-8 4-chloro-aniline 
• 938-40-9 4-Bromo-2H-1-benzopyran-2-one 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 108-95-2 phenol 
• 17831-88-8 4-chloro-2H-1-benzopyran-2-one 

Downstream Products

• 1575691-03-0 13-(4-chlorophenyl)-8-hydroxybenzo[g]chromeno[4,3-b]indol-6(13H)one 

Relevant articles and documents

Pd-Catalyzed Efficient Synthesis of Azacoumestans Via Intramolecular Cross Coupling of 4-(Arylamino)coumarins in the Presence of Copper Acetate under Microwaves1

Azacoumestans have been synthesized in excellent yields by the Pd-catalyzed oxidative coupling of 4-(arylamino)coumarins in the presence of Cu(OAc)2 in acetic acid under microwave irradiation. 4-(Arylamino)coumarins, even those substituted with an electron-withdrawing group, have been prepared almost quantitatively by the reaction of arylamines with 4-bromocoumarin under microwave irradiation in water or by Pd-catalyzed C-N coupling under heating. Preliminary biological tests indicated significant inhibition of soybean lipoxygenase and antilipid peroxidation.

Synthesis and Photophysical Properties of 1,4-Dihydro-2 H,5H-chromeno[4,3-D][1,3]oxazin-5-ones, and Derivatives Containing Tethered 1,2,3-Triazoles, from 4-Aminocoumarins

A facile protocol for the unprecedented one-pot H 2 SO 4 -mediated hydroxymethylation/cyclative N, O -acetalization of 4-aminocoumarins to 1,4-dihydro-2 H,5 H -chromeno[4,3- d ][1,3]oxazin-5-ones, in moderate to good yields, was deve

Synthesis, Cytotoxic Evaluation, and In Silico Studies of 4-Substituted Coumarins

Two series of coumarins possessing the aniline- and heterocyclic ring at 4thposition have been synthesized and evaluated for their in vitro cytotoxic activity against MCF-7 cancer cell line in MTT assay. Structure activity relationship (SAR) studies reveal that the electron donor group at position-8 of coumarin played an important role in cytotoxic activity. Compound VIId showed the potent cytotoxic activity followed by compound Xa with IC50= 6.25 and 6.50 μM, respectively. A docking study has also been carried out for the most potent compound to get an insight into molecular interactions with p50 subunit of NF-κB protein.