New selective cyclooxygenase-2 inhibitors from cyclocoumarol: Synthesis, characterization, biological evaluation and molecular modeling

被引：23

作者：

Rayar, Anita Marie ^{[1
,2
]}

Lagarde, Nathalie ^{[2
]}

Martin, Frederique ^{[3
]}

Blanchard, Florent ^{[4
]}

Liagre, Bertrand ^{[3
]}

Ferroud, Clotilde ^{[1
]}

Zagury, Jean-Francois ^{[2
]}

Montes, Matthieu ^{[2
]}

Veitia, Maite Sylla-Iyarreta ^{[1
]}

机构：

[1] Conservatoire Natl Arts & Metiers, Equipe Chim Mol, Lab CMGPCE, EA 7341, 2 Rue Conte, F-75003 Paris, France

[2] Conservatoire Natl Arts & Metiers, Lab Genet Bioinformat & Applicat, EA 4627, 2 Rue Conte, F-75003 Paris, France

[3] Univ Limoges, Lab PEIRENE, Fac Pharm, 2 Rue Dr Marcland, F-87025 Limoges, France

[4] Univ Paris Saclay, Univ Paris Sud, Inst Chim Subst Nat, CNRS,UPR 2301, Gif Sur Yvette, France

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2018年 / 146卷

关键词：

Anti-inflammatory; COX-2; inhibitors; COX-1/COX-2; inhibition; Cyclocoumarol; Cyclooxygenase; Docking study; ANTIINFLAMMATORY DRUGS; SCORING FUNCTION; DOCKING; EFFICIENT; ACCURACY; UPDATE; CANCER; AGENTS;

D O I：

10.1016/j.ejmech.2018.01.054

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In this work, a serie of cyclocoumarol derivatives was designed, synthesized, characterized and studied for their potentialities as selective inhibitors of COX-2. All target compounds have been screened for their anti-inflammatory activity by the assay of PGE2 production. Among them, compound 5d exhibited the most potent inhibitory activity with a PGE2 inhibition compared to NS-398 (79% and 88% respectively) and showed non-inhibitory activity towards the COX-1 enzyme. Docking studies revealed the capacity of this compound to occupy the selective COX-2 cavity establishing additional hydrogen bonds between the oxygen of the methoxy group and the His90 and Arg513 of the binding site of the enzyme. (C) 2018 Elsevier Masson SAS. All rights reserved.

引用

页码：577 / 587

页数：11

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