66646-97-7

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 104-94-9 4-methoxy-aniline 
• 529-20-4 2-methylphenyl aldehyde 
• 17831-88-8 4-chloro-2H-1-benzopyran-2-one 
• 108-95-2 phenol 
• 938-40-9 4-Bromo-2H-1-benzopyran-2-one 

Downstream Products

• 7348-53-0 9-methoxy-6H-chromeno[4,3-b]quinolin-6-one 
• 1575690-80-0 8-hydroxy-13-(4-methoxyphenyl)benzo[g]chromeno[4,3-b]indol-6(13H)one 

Relevant academic research and scientific papers

Synthesis of 3-aryl-4-(N-aryl)aminocoumarins via photoredox arylation and the evaluation of their biological activity

A new series of 3-aryl-4-(N-aryl)aminocoumarins was synthesized in two steps starting from the natural product 4-hydroxycoumarin using the photoredox catalysis for the key step. These conditions reactions allowed to make C[sbnd]C bonds is up to 95% yields

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.).

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

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.

Polymer grafted layered double hydroxides (LDHs-g-POEGMA): A highly efficient reusable solid catalyst for the synthesis of chromene incorporated dihydroquinoline derivatives under solvent-free conditions

A novel poly(oligoethylene glycol methacrylate)-g-supported layered double hydroxides (LDHs-g-POEGMA) with high surface area with easy accessibility of active sites was successfully prepared for the first time via an efficient sequential synthetic procedu

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.

Synthesis and antimicrobial screening of some arylaminocoumarins

The phenolic hydrolyl group of 4-hydroxycoumarins is replaced by different amines in a single step method to get new substituted 4-amino derivatives.

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