Synthesis and biological evaluation of chromone-3-carboxamides

Abstract

The aim of our study was to synthesize novel chromone-3-carboxamides and to conduct biological evaluations in search for lead compounds for the treatment of a range of debilitating disease states. Corresponding 2hydroxyacetophenones were subjected to Vilsmeier-Haack formylation to give chromone-3-carbaldehydes, which were subsequently oxidised to give chromone-3-carboxylic acids. Treatment of the carboxylic acids with thionyl chloride resulted in the in situ formation of the corresponding acid chlorides, which were reacted with various amines in the presence of triethylamine to give the corresponding novel chromone-3-carboxamides in good yields. Selected chromone derivatives were then evaluated for their anti-inflammatory, antitryponosomal and cytotoxic properties.

Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

“…13 Analogously, with a superior inhibitory activity toward human MAO-B (Monoamine oxidase B) compared to chromone-2-carboxamide counterparts, tremendous examples of chromone-3-carboxamides (Figure 1) have been described as potent inhibitors of human acetylcholinesterase I, 14 and as activators of defective or malfunctioning nicotinic acetylcholine receptors (nAChR), especially of the brain II. 15 different structural analogs have been documented as antiallergic III for the management of passive cutaneous anaphylaxis, 16 as cytotoxic IV, 17 and as anti-inflammatory agents V. 17 On the other hand, transition metal-catalyzed carbonylative cross-coupling reactions have emerged as a captivating powerful tool to introduce one or two carbonyl motif into aryl-, heteroaryl-, alkenyl halides, and alternative activated substrates, yielding new functionalities such as amides, ketoamides, carbamates, aldehydes, ketones, carboxylic acids, etc. 18 Particularly, palladium-catalyzed aminocarbonylation as a highly chemoselective one-step transformation showed tolerance for a wide range of nucleophiles and functionalities.…”

“…Analogously, with a superior inhibitory activity toward human MAO-B (Monoamine oxidase B) compared to chromone-2-carboxamide counterparts, tremendous examples of chromone-3-carboxamides ( Figure 1 ) have been described as potent inhibitors of human acetylcholinesterase I , 14 and as activators of defective or malfunctioning nicotinic acetylcholine receptors (nAChR), especially of the brain II . 15 Furthermore, different structural analogs have been documented as antiallergic III for the management of passive cutaneous anaphylaxis, 16 as cytotoxic IV , 17 and as anti-inflammatory agents V . 17 …”

“…15 Furthermore, different structural analogs have been documented as antiallergic III for the management of passive cutaneous anaphylaxis, 16 as cytotoxic IV , 17 and as anti-inflammatory agents V . 17 …”