183232-64-6Relevant academic research and scientific papers
Divalent cannabinoid-1 receptor ligands: A linker attachment point survey of SR141716A for development of high-affinity CB1R molecular probes
Grant, Phillip S.,Kahlcke, Nils,Govindpani, Karan,Hunter, Morag,MacDonald, Christa,Brimble, Margaret A.,Glass, Michelle,Furkert, Daniel P.
, (2019/10/02)
The cannabinoid-1 receptor (CB1R) inverse agonist SR141716A has proven useful for study of the endocannabinoid system, including development of divalent CB1R ligands possessing a second functional motif attached via a linker unit. These have predominantly employed the C3 position of the central pyrazole ring for linker attachment. Despite this precedent, a novel series of C3-linked CB1R-D2R divalent ligands exhibited extremely high affinity at the D2R, but only poor affinity for the CB1R. A systematic linker attachment point survey of the SR141716A pharmacophore was therefore undertaken, establishing the C5 position as the optimal site for linker conjugation. This linker attachment survey enabled the identification of a novel divalent ligand as a lead compound to inform ongoing development of high-affinity CB1R molecular probes.
Discovery of 2-[5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-ethyl-1H- pyrazol-3-yl]-1,5,5-trimethyl-1,5-dihydro-imidazol-4-thione (BPR-890) via an active metabolite. A novel, potent and selective cannabinoid-1 receptor inverse agonist with high antiobes
Wu, Chien-Huang,Hung, Ming-Shiu,Song, Jen-Shin,Yeh, Teng-Kuang,Chou, Ming-Chen,Chu, Cheng-Ming,Jan, Jiing-Jyh,Hsieh, Min-Tsang,Tseng, Shi-Liang,Chang, Chun-Ping,Hsieh, Wan-Ping,Lin, Yinchiu,Yeh, Yen-Nan,Chung, Wan-Ling,Kuo, Chun-Wei,Lin, Chin-Yu,Shy, Horng-Shing,Chao, Yu-Sheng,Shia, Kak-Shan
experimental part, p. 4496 - 4510 (2010/03/01)
By using the active metabolite 5 as an initial template, further structural modifications led to the identification of the titled compound 24 (BPR-890) as a highly potent CB1 inverse agonist possessing an excellent CB2/1 selectivity and remarkable in vivo
Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists
Lan, Ruoxi,Liu, Qian,Fan, Pusheng,Lin, Sonyuan,Fernando, Susanthi R.,McCallion, Deirdre,Pertwee, Roger,Makriyannis, Alexandras
, p. 769 - 776 (2007/10/03)
As a potent, specific antagonist for the brain cannabinoid receptor (CB1), the biarylpyrazole N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4- dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A; 1) was the lead compound for initiating studies desi
Preparation of iodine-123 labeled AM251: A potential spect radioligand for the brain cannabinoid CB1 receptor
Lan, Ruoxi,Gatley, S. John,Makriyannis, Alexandros
, p. 875 - 881 (2007/10/03)
We report the synthesis and labeling with iodine-123 of N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole -3-carboxamide (AM251). This compound is an anlog of the recently described cannabinoid receptor antagonist, R141716A,
