期刊
MOLECULAR DIVERSITY
卷 21, 期 2, 页码 339-354出版社
SPRINGER
DOI: 10.1007/s11030-017-9734-y
关键词
DKHDA reaction; Ketone-based DKHDA substrates; Benzopyran; Pyrano[2,3-c]pyrazole; Antiproliferative activity
类别
资金
- University Grants Commission (UGC), New Delhi under the UGC Scheme of Major Research Project [39-822/2010 (SR)]
- UGC, New Delhi
- EU Research Potential [FP7-REGPOT-2012-CT2012-31637-IMBRAIN]
- European Regional Development Fund (FEDER)
- Spanish Instituto de Salud Carlos III [PI11/00840]
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.
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