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

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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.

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Acknowledgements

The authors are thankful to the Head, Department of Chemistry, Sardar Patel University, for providing necessary research facilities. We are also thankful to the University Grants Commission (UGC), New Delhi, for financial support under the UGC Scheme of Major Research Project (F. No: 39-822/2010 (SR) dated 11.01.2011). Authors (BML, TRS and GCB) are grateful to the UGC, New Delhi, for research fellowship. Co-financed by the EU Research Potential (FP7-REGPOT-2012-CT2012-31637-IMBRAIN), the European Regional Development Fund (FEDER), and the Spanish Instituto de Salud Carlos III (PI11/00840).

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Authors and Affiliations

  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Dist. Anand, Gujarat, 388120, India

    Balvantsingh M. Labana, Gaurangkumar C. Brahmbhatt, Tushar R. Sutariya & Narsidas J. Parmar

  2. 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

    José M. Padrón

  3. Post-Graduate Department of Physics, University of Jammu, Jammu Tawi, 180006, India

    Rajni Kant & Vivek K. Gupta

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  1. Balvantsingh M. Labana
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Correspondence to Narsidas J. Parmar.

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Labana, B.M., Brahmbhatt, G.C., Sutariya, T.R. et al. Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives. Mol Divers 21, 339–354 (2017). https://doi.org/10.1007/s11030-017-9734-y

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  • DOI: https://doi.org/10.1007/s11030-017-9734-y

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