33543-89-4

Upstream product

• 5112-47-0 4-oxo-4H-chromene-2-carbonyl chloride 
• 80253-60-7 1-methyl-1-(4-oxochromen-2-yl)ethyl 4-oxochromen-2-carboxylate 
• 80253-65-2 cyanomethyl 4-oxochromen-2-carboxylate 
• 4940-39-0 acide chromone carboxylique-2 

Downstream Products

• 33543-90-7 Chromone-2-carbonitrile 

Relevant academic research and scientific papers

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.

Benzopyrones. Part 17. The Synthesis of some Bischromones and the Reaction of Cyanomethyl Esters with Sodium Azide

Treatment of 4-oxochromen-2-carboxyl chloride with dimethylcadmium gave 1-methyl-1-(4-oxochromen-2-yl)ethyl 4-oxochromen-2-carboxylate (11) which was synthesized unequivocally and degraded to the carboxylic acid and 2-(1-methylvinyl)chromen-4-one. 2-Acetylchromen-4-one was synthesized by a new and more efficient method from 4-oxochromen-2-carbonyl chloride.The synthesis and some reactions of 4-oxochromen-2-yl isocyanate, and the cyanomethyl esters of 4-oxochromen-2-carboxylic and -2,6-dicarboxylic acids are descibed.