Affiliations 

  • 1 Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea
  • 2 Department of Chemistry, Kongju National University, Gongju, Chungnam 32588, Republic of Korea
  • 3 Institute of Molecular Biology and Biotechnology, The University of Lahore, Defence Road, Lahore 54590, Pakistan
  • 4 School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia (UKM), 43600 Bangi, Selangor, Malaysia. Electronic address: jalifah@ukm.edu.my
  • 5 Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea. Electronic address: dnalove@kongju.ac.kr
Bioorg Chem, 2019 11;92:103201.
PMID: 31445195 DOI: 10.1016/j.bioorg.2019.103201

Abstract

We have carried out the synthesis of new 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamide derivatives by the reaction between isatoic anhydride, 2-furoic hydrazide and substituted salicylaldehydes in ethanol: water (5:5 v/v) solvent system using p-TSA as a catalyst under ultrasound irradiation at room temperature. The structures of newly synthesized compounds were confirmed through spectral techniques such as IR, 1H NMR, 13C NMR, and LCMS. The important features of this protocol include simple and easy workup procedure, reaction carried out at ambient temperature, use of ultrasound and high yield of oxoquinazolin-3(4H)-yl)furan-2-carboxamides in short reaction time. The synthesized compounds 4a-4j were screened against tyrosinase enzyme and all these compounds found to be potent inhibitors with much lower IC50 value of 0.028 ± 0.016 to 1.775 ± 0.947 µM than the standard kojic acid (16.832 ± 1.162 µM). The kinetics mechanism for compound 4e was analyzed by Lineweaver-Burk plots which revealed that compound inhibited tyrosinase non-competitively by forming an enzyme-inhibitor complex. Along with this all the synthesized compounds (4a-4j) were scanned for their DPPH free radical scavenging ability. The outputs received through in vitro and in silico analysis are coherent to the each other with good binding energy values (kcal/mol) posed by synthesized ligands.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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