DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF 5-OXO-1,4,5,6,7,8 HEXAHYDROQUINOLINE DERIVATIVES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS

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ZARGHI AFSHIN; SABAKHI IMAN; TOPUZYAN VIGEN; HAJIMAHDI ZAHRA; DARAIE BAHRAM

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Journal: Iranian Journal of Pharmaceutical Research Year:2014 | Volume:13 | Issue:SUPPL Page(s): 61-69

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Title

DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF 5-OXO-1,4,5,6,7,8 HEXAHYDROQUINOLINE DERIVATIVES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS

Author(s)

Keywords

5-OXO-1

8 HEXAHYDROQUINOLINES

COX-2 INHIBITORS

MOLECULAR MODELING

HANSCH CONDENSATION

Abstract

A group of regioisomeric 5-OXO-1, 4, 5, 6, 7, 8 hexahydroquinoline derivatives possessing a COX-2 SO2Me pharmacophore at the para position of the C-2 or C-4 phenyl ring, in conjunction with a C-4 or C-2 phenyl (4-H) or substituted-phenyl ring (4-F, 4-Cl, 4-Br, 4-OMe, 4-Me, 4-NO2), were designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. These target 5-OXO-1, 4, 5, 6, 7, 8 HEXAHYDROQUINOLINES were synthesized via a HANSCH CONDENSATION reaction. In vitro COX-1/COX-2 isozyme inhibition structure-activity studies identified 7, 8-dihydro- 7, 7-dimethyl-2- (4-methoxyphenyl) -4- (4- (methylsulfonyl) phenyl) quinolin-5 (1H, 4H, 6H) - one (9c) as a potent COX-2 inhibitor (IC50=0.17 M) with a high COX-2 selectivity index (S.I.=97.6) comparable to the reference drug celecoxib (COX-2 IC50=0.05 mM; COX-2 S.I=405). A MOLECULAR MODELING study where 9c was docked in active site of COX-2 showed that the p-SO2Me substituent on the C-2 phenyl ring is inserted into the secondary COX-2 binding site. The structure activity data acquired indicate that the position of the COX-2 SO2Me pharmacophore and type of substituent are important for COX-2 inhibitory activity.

Cites

DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF NEW 1, 4-DIHYDROPYRIDINE (DHP) DERIVATIVES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS

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APA: Copy

ZARGHI, AFSHIN, SABAKHI, IMAN, TOPUZYAN, VIGEN, HAJIMAHDI, ZAHRA, & DARAIE, BAHRAM. (2014). DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF 5-OXO-1,4,5,6,7,8 HEXAHYDROQUINOLINE DERIVATIVES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), 13(SUPPL), 61-69. SID. https://sid.ir/paper/288426/en

Vancouver: Copy

ZARGHI AFSHIN, SABAKHI IMAN, TOPUZYAN VIGEN, HAJIMAHDI ZAHRA, DARAIE BAHRAM. DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF 5-OXO-1,4,5,6,7,8 HEXAHYDROQUINOLINE DERIVATIVES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS. IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR)[Internet]. 2014;13(SUPPL):61-69. Available from: https://sid.ir/paper/288426/en

IEEE: Copy

AFSHIN ZARGHI, IMAN SABAKHI, VIGEN TOPUZYAN, ZAHRA HAJIMAHDI, and BAHRAM DARAIE, “DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF 5-OXO-1,4,5,6,7,8 HEXAHYDROQUINOLINE DERIVATIVES AS SELECTIVE CYCLOOXYGENASE-2 INHIBITORS,” IRANIAN JOURNAL OF PHARMACEUTICAL RESEARCH (IJPR), vol. 13, no. SUPPL, pp. 61–69, 2014, [Online]. Available: https://sid.ir/paper/288426/en

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