24526-89-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Chloroanilino)-2H-chromen-2-one is used as an anticancer agent for its potential therapeutic implications in the treatment of cancers. It inhibits the Wnt/β-catenin signaling pathway, which is often dysregulated in various types of cancer, leading to uncontrolled cell proliferation and tumor growth.
Used in Anti-inflammatory Applications:
4-(4-Chloroanilino)-2H-chromen-2-one is used as an anti-inflammatory agent due to its ability to modulate the Wnt/β-catenin signaling pathway, which is involved in inflammatory processes. By inhibiting this pathway, it may help reduce inflammation and alleviate symptoms associated with inflammatory diseases.
Used in Stem Cell Therapy:
4-(4-Chloroanilino)-2H-chromen-2-one is used as a promoter of stem cell differentiation, which has potential applications in regenerative medicine. Its ability to induce differentiation of stem cells into specific cell types may contribute to the development of novel treatments for various diseases and tissue repair.
Used in Tissue Repair and Regeneration:
4-(4-Chloroanilino)-2H-chromen-2-one is used for its potential role in repairing tissue damage and promoting tissue regeneration. Its ability to modulate the Wnt/β-catenin signaling pathway may contribute to the healing process and restoration of damaged tissues, offering new therapeutic approaches for various conditions.

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 academic research and scientific papers

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.

Electrooxidative Metal-Free Cyclization of 4-Arylaminocoumarins with DMF as C1-Source

An environmentally-benign electrochemical approach for the construction of quinoline derivatives employing N,N-dimethylformamide (DMF) as the methine source has been devised by cyclization of 4-(phenylamino)-2H-chromen-2-ones. In a user-friendly undivided cell, 6H-chromeno[4,3-b]quinolin-6-ones were obtained under chemical oxidant-free and transition-metal-free conditions in 43–92% yields with high functional tolerance. (Figure presented.).

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

Copper-Catalyzed Cyclization for Access to 6H-Chromeno[4,3-b]quinolin-6-ones Employing DMF as the Carbon Source

The first example of the copper-catalyzed cyclization of 4-(phenylamino)-2H-chromen-2-ones employing the N-methyl moiety of DMF as the source of the methine (CH) group has been developed, providing an efficient synthetic pathway to access novel functional

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.

Screening for in vitro antimycobacterial activity and three-dimensional quantitative structure-activity relationship (3D-QSAR) study of 4-(arylamino)coumarin derivatives

The resurgence of tuberculosis and the emergence of multidrug-resistant strains of Mycobacteria necessitate the search for new classes of antimycobacterial agents. We have synthesized a small library of 50 analogues of 4-(arylamino)coumarins with various aromatic amines at the C4-position of the coumarin scaffold. The compounds were evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Rv with rifampicin as the standard. Of the molecules synthesized, compound 9 was found to be most potent with a minimum inhibitory concentration >6.25 lg/mL for 100% inhibition. In an effort to develop new and more effective molecules in this series, the relationship between structure and activity was investigated by comparative molecular field analysis. Various models were generated using comparative molecular field analysis alone and comparative molecular field analysis plus a hydropathy field (HINT). In all, eight models were generated with atom-fit and field-fit alignment strategies. The comparative molecular field analysis models (Models 3a and 4a) based on field-fit alignment were the best with statistically good correlation coefficients (r2) and cross-validated q2. The values of r2pred for the validation set were 0.469 and 0.516. Based on the comparative molecular field analysis contours, some insights into the structure-activity relationship of the compounds could be gained.

Microwave assisted synthesis of 4-aryl/alkylaminocoumarins

4-Aryl and 4-alkylaminocoumarins were prepared by reaction of 4-hydroxycoumarin with amines under microwave irradiation in solvent-free conditions in good to excellent yields.

A Novel Transformation of 4-Arylaminocoumarins to 6H-1-Benzopyranoquinolin-6-ones Under Vilsmeier-Haack Conditions

4-Aryl and 4-alkylaminocoumarins 1 were prepared by reacting of 4-hydroxycoumarin and an appropriate amine.The reaction of 1 with phosphorousoxychloride/dimethylformamide led to 6H-1-benzopyranoquinoline-6-one derivatives 2 in very good yields, whi