Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives

• Published in: Molecular diversity 2017-05, Vol.21 (2), p.339-354
• Main Authors: Labana, Balvantsingh M., Brahmbhatt, Gaurangkumar C., Sutariya, Tushar R., Parmar, Narsidas J., Padrón, José M., Kant, Rajni, Gupta, Vivek K.
• Format: Article
• Language: English
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Bacteria - drug effects; Benzopyrans - chemistry; Biochemistry; Biomedical and Life Sciences; Cell growth; Cell Line, Tumor; Chemical compounds; Chemical reactions; Chemical synthesis; Chemistry Techniques, Synthetic; Fungi - drug effects; Humans; Life Sciences; Organic Chemistry; Original Article; Pharmacy; Polymer Sciences; Pyrazoles - chemical synthesis; Pyrazoles - chemistry; Pyrazoles - pharmacology
• ISSN: 1381-1991; 1573-501X
• DOI: 10.1007/s11030-017-9734-y

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. Graphical Abstract