title: Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives.
abstract: 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.
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Dist. Anand, Gujarat, 388120, India.
authors.forename: Balvantsingh M
authors.initials: BM
authors.lastname: Labana
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Dist. Anand, Gujarat, 388120, India.
authors.forename: Gaurangkumar C
authors.initials: GC
authors.lastname: Brahmbhatt
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Dist. Anand, Gujarat, 388120, India.
authors.forename: Tushar R
authors.initials: TR
authors.lastname: Sutariya
authors.affiliation: Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Dist. Anand, Gujarat, 388120, India. njpchemdeptspu@yahoo.co.in.
authors.forename: Narsidas J
authors.initials: NJ
authors.lastname: Parmar
authors.affiliation: BioLab, Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206, La Laguna, Spain.
authors.forename: José M
authors.initials: JM
authors.lastname: Padrón
authors.affiliation: Post-Graduate Department of Physics, University of Jammu, Jammu Tawi, 180006, India.
authors.forename: Rajni
authors.initials: R
authors.lastname: Kant
authors.affiliation: Post-Graduate Department of Physics, University of Jammu, Jammu Tawi, 180006, India.
authors.forename: Vivek K
authors.initials: VK
authors.lastname: Gupta
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001578:Benzopyrans / Q000737:chemistry*; D045744:Cell Line, Tumor; D060326:Chemistry Techniques, Synthetic; D005658:Fungi / Q000187:drug effects; D006801:Humans; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D001578:Benzopyrans; D011720:Pyrazoles; C031280:pyrazole
keywords: Antiproliferative activity; Benzopyran; DKHDA reaction; Ketone-based DKHDA substrates; Pyrano[2,3-c]pyrazole