Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives.
A one-pot method has been described to synthesize benzopyran-annulated pyrano[2,3-c]pyrazoles, effectively by combining O-alkenyloxy/alkynyloxy-acetophenones with various pyrazolones in triethylammonium acetate (TEAA) under microwave irradiation. While combination of O-allyloxy- or O-prenyloxy-acetophenones with pyrazolones occurred efficiently, that of O-propargyloxy-acetophenones was found effective in the presence of ZnO catalyst, via a domino Knoevenagel-hetero-Diels-Alder (DKHDA) reaction. Aminobenzopyran frameworks were also synthesized, after nitro-containing products were reduced in tandem with iron(II) in an acidic medium. The in vitro antiproliferative activity of these compounds was measured and discussed against gram-positive, gram-negative and M. tuberculosis bacteria, fungi, and various representative human solid tumor cell lines, in addition to their ferric reducing antioxidant capability.
['Labana|Balvantsingh M|BM|', 'Brahmbhatt|Gaurangkumar C|GC|', 'Sutariya|Tushar R|TR|', 'Parmar|Narsidas J|NJ|', 'Padrón|José M|JM|', 'Kant|Rajni|R|', 'Gupta|Vivek K|VK|']
D000890:Anti-Infective Agents D000970:Antineoplastic Agents D001419:Bacteria D001578:Benzopyrans D045744:Cell Line, Tumor D060326:Chemistry Techniques, Synthetic D005658:Fungi D006801:Humans D011720:Pyrazoles
Pyrano[2,3-c]pyrazole Antiproliferative activity Benzopyran DKHDA reaction Ketone-based DKHDA substrates