期刊
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
卷 149, 期 -, 页码 98-109出版社
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2018.02.037
关键词
Antiviral agents; West Nile Virus; Indan-1,3-dione; Knoevenagel condensation
资金
- National Counsel of Technological and Scientific Development (CNPq)
- Foundation for Supporting Research in the state of Minas Gerais (FAPEMIG)
- National Program for Academic Cooperation (PROCAD) of the Coordination for the Improvement of Higher Education Personnel-CAPES/Brazil
A simple and efficient Knoevenagel procedure for the synthesis of 2-arylidene indan-1,3-diones is herein reported. These compounds were prepared via ZrOCl2 center dot 8H2O catalyzed reactions of indan-1,3-dione with several aromatic aldehydes and using water as the solvent. The 2-arylidene indan-1,3-diones were obtained with 53%-95% yield within 10-45 min. The synthesized compounds were evaluated as inhibitors of the NS2B-NS3 protease of West Nile Virus (WNV). It was found that hydroxylated derivatives impaired enzyme activity with varying degrees of effectiveness. The most active hydroxylated derivatives, namely 2-(4-hydroxybenzylidene)-1H-indene-1,3(2H)-dione (14) and 2-(3,4-di hyd roxybenzylidene)-1H-indene1,3 (2H)-dione (17), were characterized as noncompetitive enzymes inhibitors, with IC50 values of 11 mu mol L-1 and 3 mu mol L-1, respectively. Docking and electrostatic potential surfaces investigations provided insight on the possible binding mode of the most active compounds within an allosteric site. (C) 2018 Elsevier Masson SAS. All rights reserved.
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