175422-57-8

Basic information

• Product Name: 4-amino-5-chloro-2-methoxy-3-(2-propenyl)benzoic acid
• Synonyms: 4-amino-5-chloro-2-methoxy-3-(2-propenyl)benzoic acid
• CAS NO: 175422-57-8
• Molecular Weight: 241.674
• Mol File: 175422-57-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 4-amino-5-chloro-2-methoxy-3-(2-propenyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-5-chloro-2-methoxy-3-(2-propenyl)benzoic acid(175422-57-8)
• EPA Substance Registry System: 4-amino-5-chloro-2-methoxy-3-(2-propenyl)benzoic acid(175422-57-8)

Safety Data

• Hazardous Substances Data: 175422-57-8(Hazardous Substances Data)

Upstream product

• 129511-07-5 methyl 3-allyl-2-hydroxy-4-acetylamino-5-chlorobenzoate 
• 111049-87-7 methyl 4-acetylamino-2-allyloxy-5-chlorobenzoate 
• 91958-13-3 methyl 2-allyloxy-4-acetylaminobenzoate 
• 4093-28-1 methyl 4-acetamido-2-hydroxybenzoate 
• 129529-37-9 methyl 3-allyl-2-methoxy-4-acetylamino-5-chlorobenzoate 

Relevant 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

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.