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Ultrasound mediated efficient synthesis of new 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as potent tyrosinase inhibitors: Mechanistic approach through chemoinformatics and molecular docking studies.
Bioorg Chem. 2019 11; 92:103201.BC

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.

Authors+Show Affiliations

Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea.Department of Chemistry, Kongju National University, Gongju, Chungnam 32588, Republic of Korea.Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea.Institute of Molecular Biology and Biotechnology, The University of Lahore, Defence Road, Lahore 54590, Pakistan.Department of Chemistry, Kongju National University, Gongju, Chungnam 32588, Republic of Korea.Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea.Department of Chemistry, Kongju National University, Gongju, Chungnam 32588, Republic of Korea.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.Department of Biological Sciences, Kongju National University, Gongju, Chungnam 32588, Republic of Korea. Electronic address: dnalove@kongju.ac.kr.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31445195

Citation

Dige, Nilam C., et al. "Ultrasound Mediated Efficient Synthesis of New 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as Potent Tyrosinase Inhibitors: Mechanistic Approach Through Chemoinformatics and Molecular Docking Studies." Bioorganic Chemistry, vol. 92, 2019, p. 103201.
Dige NC, Mahajan PG, Raza H, et al. Ultrasound mediated efficient synthesis of new 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as potent tyrosinase inhibitors: Mechanistic approach through chemoinformatics and molecular docking studies. Bioorg Chem. 2019;92:103201.
Dige, N. C., Mahajan, P. G., Raza, H., Hassan, M., Vanjare, B. D., Hong, H., Hwan Lee, K., Latip, J., & Seo, S. Y. (2019). Ultrasound mediated efficient synthesis of new 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as potent tyrosinase inhibitors: Mechanistic approach through chemoinformatics and molecular docking studies. Bioorganic Chemistry, 92, 103201. https://doi.org/10.1016/j.bioorg.2019.103201
Dige NC, et al. Ultrasound Mediated Efficient Synthesis of New 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as Potent Tyrosinase Inhibitors: Mechanistic Approach Through Chemoinformatics and Molecular Docking Studies. Bioorg Chem. 2019;92:103201. PubMed PMID: 31445195.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ultrasound mediated efficient synthesis of new 4-oxoquinazolin-3(4H)-yl)furan-2-carboxamides as potent tyrosinase inhibitors: Mechanistic approach through chemoinformatics and molecular docking studies. AU - Dige,Nilam C, AU - Mahajan,Prasad G, AU - Raza,Hussain, AU - Hassan,Mubashir, AU - Vanjare,Balasaheb D, AU - Hong,Hansol, AU - Hwan Lee,Ki, AU - Latip,Jalifah, AU - Seo,Sung-Yum, Y1 - 2019/08/13/ PY - 2019/07/10/received PY - 2019/08/08/revised PY - 2019/08/13/accepted PY - 2019/8/25/pubmed PY - 2019/8/25/medline PY - 2019/8/25/entrez KW - Drug score KW - Lipinski’s rule KW - Molecular docking KW - Oxoquinazolin-3(4H)-yl)furan-2-carboxamides KW - Tyrosinase KW - Ultrasound sonication SP - 103201 EP - 103201 JF - Bioorganic chemistry JO - Bioorg. Chem. VL - 92 N2 - 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. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/31445195/Ultrasound_mediated_efficient_synthesis_of_new_4_oxoquinazolin_3_4H__yl_furan_2_carboxamides_as_potent_tyrosinase_inhibitors:_Mechanistic_approach_through_chemoinformatics_and_molecular_docking_studies_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(19)31092-2 DB - PRIME DP - Unbound Medicine ER -
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