Labana Balvantsingh M, Brahmbhatt Gaurangkumar C, Sutariya Tushar R, Parmar Narsidas J, Padrón José M, Kant Rajni, Gupta Vivek K
Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Dist. Anand, Gujarat, 388120, India.
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.
Mol Divers. 2017 May;21(2):339-354. doi: 10.1007/s11030-017-9734-y. Epub 2017 Mar 14.
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.
已经描述了一种一锅法来合成苯并吡喃稠合的吡喃并[2,3 - c]吡唑，该方法通过在微波辐射下，将O - 烯基氧基/炔基氧基苯乙酮与各种吡唑啉酮在三乙铵乙酸盐（TEAA）中有效结合来实现。虽然O - 烯丙氧基或O - 异戊烯氧基苯乙酮与吡唑啉酮的结合反应高效，但发现O - 炔丙氧基苯乙酮在ZnO催化剂存在下，通过多米诺Knoevenagel - 杂环狄尔斯 - 阿尔德（DKHDA）反应是有效的。在含硝基产物在酸性介质中与亚铁离子串联还原后，还合成了氨基苯并吡喃骨架。除了这些化合物的铁还原抗氧化能力外，还测定并讨论了它们对革兰氏阳性菌、革兰氏阴性菌、结核分枝杆菌、真菌以及各种代表性人类实体瘤细胞系的体外抗增殖活性。
