3845-17-8

Basic information

• Product Name: N-(4-methylphenyl)-4-oxo-4H-1-benzopyran-2-carboxamide
• Synonyms: N-(4-methylphenyl)-4-oxo-4H-1-benzopyran-2-carboxamide
• CAS NO: 3845-17-8
• Molecular Weight: 279.295
• Mol File: 3845-17-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(4-methylphenyl)-4-oxo-4H-1-benzopyran-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-methylphenyl)-4-oxo-4H-1-benzopyran-2-carboxamide(3845-17-8)
• EPA Substance Registry System: N-(4-methylphenyl)-4-oxo-4H-1-benzopyran-2-carboxamide(3845-17-8)

Safety Data

• Hazardous Substances Data: 3845-17-8(Hazardous Substances Data)

Upstream product

• 4940-39-0 acide chromone carboxylique-2 
• 106-49-0 p-toluidine 
• 5112-47-0 4-oxo-4H-chromene-2-carbonyl chloride 

Relevant articles and documents

Synthesis and evaluation of chromone-2-carboxamide derivatives as cytotoxic agents and 5-lipoxygenase inhibitors

In the present study, we prepared a series of 21 chromone carboxamide derivatives bearing diverse amide side chains. Their potency to inhibit the proliferation of breast (MCF-7), ovarian (OVCAR and IGROV), and colon (HCT-116) cancer cell lines, was evaluated in vitro using the MTT assay. Among these compounds, 13 showed promising cytotoxic activity against at least one cancer cell line with IC50 in the range 0.9–10 μM. Our compounds were also screened for their anti-inflammatory activity as putative inhibitors of 5-lipoxygenase. Structure-activity relationships studies on our chromone carboxamide derivatives revealed that the presence of a 6-fluoro substituent on the chromone nucleus (R1) or propyl and 3-ethylphenyl groups on the amide side chain (R2) has a positive impact on the cytotoxic activity. In terms of the anti-inflammatory activity, hydrophilic chromone carboxamide derivatives showed greater 5-lipoxygenase inhibition. The physico-chemical properties of chromone carboxamides are in accordance with the general requirements of drug development process and ligand efficiency values allow further structure optimization, with compound 4b as a lead.

Accelerating lead optimization of chromone carboxamide scaffold throughout microwave-assisted organic synthesis

Microwave irradiation offers a considerable advantage over conventional synthesis with rate enhancements and cleaner reactions. Accordingly, a new microwave-assisted method for the synthesis of func-tionalized chromones was developed allowing the obtention of a library of chromone carboxamides. The method has been shown to present several advantages including operational simplicity, good performance, significant reduction in reaction time, less formation of by-products, and easier work-up.