Synthesis, potential anti-inflammatory and analgesic activities study of (S)-N-substituted-1-phenyl-3, 4-dihydroisoquinoline-2(1H)-carboxamides. Issue 15 (1st August 2017)

• Record Type: Journal Article
• Authors: Guan, Li-Ping; Xia, Ya-Nan; Jin, Qing-Hao; Liu, Bing-Yu; Wang, Si-Hong
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 27:Issue 15(2017)
• Page Start: 3378
• Page End: 3381
• Publication Date: 2017-08-01
• Subjects: Isoquinoline-2(1H)-carboxamides -- Anti-inflammatory -- Analgesic -- COX-1/COX-2 -- Inhibition assay; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2017.06.002
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A series of ( S )- N -substitued-1-phenyl-3, 4-dihydroisoquinoline-2(1 H )-carboxamide derivatives were designed, synthesized and evaluated for their anti-inflammatory and analgesic effects in vivo . Among the synthesized compounds2a and2n showed the best anti-inflammatory activity (inhibition rate: 95% and 92.7%, respectively) and analgesic effect (inhibition rate: 100% and 100%, respectively), which was greater than that or nearly equivalent to that of indomethacin. Compounds2a and2n were selected to test their inhibitory effects against ovine COX-1 and COX-2 using the cyclooxygenase inhibition assay in vitro . Compounds2a and2n are weak inhibitors of COX-1 isozyme but displayed moderate COX-2 isozyme inhibitory effects (IC50 = 0.47 μM and 1.63 μM, respectively) and COX-2 selectivity indexes (SI = 11.5 and 4.8). Furthermore, compound2a was more inhibitors of COX-2 isozyme active than the reference drug celecoxib.