132976-79-5Relevant articles and documents
Synthesis and structure-activity relationship of 3-substituted benzamide, benzo[b]furan-7-carboxamide, 2,3-dihydrobenzo[b]furan-7- carboxamide, and indole-5-carboxamide derivatives as selective serotonin 5- HT4 receptor agonists
Kakigami, Takuji,Usui, Toshinao,Tsukamoto, Katsura,Kataoka, Tadashi
, p. 42 - 52 (2007/10/03)
The title compounds (6-9) were prepared and evaluated for serotonin 5- HT4 agonistic activity in in vitro tests. Introducing a propyl or allyl group at the 3-position of benzamide caused only a slight enhancement of agonistic activity. Construction of the benzo[b']furan skeleton and 2,3- dihydrobenzo[b]furan skeleton caused a significant enhancement of the activity. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2- methylbenzo[b]furan-7-carboxamide (7b) hemifumarate was as potent as cisapride. 4-Amino-N-[2-(1-azabicyclo[3.3.0]octan-5-yl)ethyl]-5-chloro-2,3- dihydro-2-methylbenzo[b]furan-7-carboxamide (8a) hemifumarate, 4-amino-N-[2- (1-azabicyclo [3.3.0]octan-5-yl)ethyl]5-chloro-2,3-dihydro-2- ethylbenzo[b]furan-7-carboxamide (8c) hemifumarate, and 4-amino-N-]2-(1- azabicyclo[3.3.0]octan-5-yl]-5-chloro-2,3-dihydro-2,3-dimethylhenzo[b]furan- 7-carboxamide (8d) hemifumarate were more potent than cisapride. Furthermore, 8a hemifumarate was free from dopamine D1, D2, serotonin 5-HT1, 5-HT2 and muscarine M1, M2 receptor binding activity in the in vitro tests. On the other hand, construction of the indole skeleton caused a remarkable decrease in activity.
