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Tricyclic pyrazoles. Part 2: Synthesis and biological evaluation of novel 4,5-dihydro-1H-benzo[g]indazole-based ligands for cannabinoid receptors.

作者信息

Murineddu Gabriele, Ruiu Stefania, Mussinu Jean-Mario, Loriga Giovanni, Grella Giuseppe E, Carai Mauro A M, Lazzari Paolo, Pani Luca, Pinna Gérard A

机构信息

Dipartimento Farmaco Chimico Tossicologico, Università di Sassari, via F. Muroni 23/A, 07100 Sassari, Italy.

出版信息

Bioorg Med Chem. 2005 May 2;13(9):3309-20. doi: 10.1016/j.bmc.2005.02.032.

DOI:10.1016/j.bmc.2005.02.032
PMID:15809166
Abstract

A series of 4,5-dihydro-1H-benzo[g]indazole-3-carboxamides (2a-k) as analogues of the previously reported CB(2) ligands 6-chloro- and 6-methyl-1-(2',4'-dichlorophenyl)-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c]pyrazole-3-carboxamides (1a,b) was synthesized and their affinity and selectivity towards CB(1) and CB(2) receptors were evaluated. Several of the new compounds (2a,b,c,d and i) exhibited CB(1) affinity in the nanomolar range with moderate or negligible affinity towards CB(2) receptors. Compounds 2a and c increased intestinal propulsion in mouse. Their pro-kinetic effects were reversed by the reference CB agonist CP-55,940. Consequently, in vivo CB(1) antagonistic activity was highlighted for these compounds.

摘要

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