174486-39-6

Basic information

• Product Name: endo-N-[8-(3-Hydroxypropyl)-8-azabicyclo[3.2.1]oct-3-yl]-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide
• Synonyms: TS-951
• CAS NO: 174486-39-6
• Molecular Formula: C₂₃H₃₁N₃O₃
• Molecular Weight: 397.52182
• Mol File: 174486-39-6.mol

Chemical Properties

• CAS DataBase Reference: endo-N-[8-(3-Hydroxypropyl)-8-azabicyclo[3.2.1]oct-3-yl]-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: endo-N-[8-(3-Hydroxypropyl)-8-azabicyclo[3.2.1]oct-3-yl]-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide(174486-39-6)
• EPA Substance Registry System: endo-N-[8-(3-Hydroxypropyl)-8-azabicyclo[3.2.1]oct-3-yl]-1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxamide(174486-39-6)

Safety Data

• Hazardous Substances Data: 174486-39-6(Hazardous Substances Data)

Upstream product

• 174486-98-7 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid chloride 
• 627-18-9 1-bromo-3-propanol 
• 5344-90-1 2-Aminobenzyl alcohol 
• 5226-51-7 2,2-dimethyl-1,4-dihydro-2H-3,1-benzoxazine 
• 106898-71-9 2-isopropylaminobenzyl alcohol 
• 158577-01-6 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 103323-43-9 8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octan-3-one 
• 731763-25-0 8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octan-3-one oxime hydrochloride 
• 103718-15-6 2-(isopropylamino)benzaldehyde 

Relevant articles and documents

Synthesis and evaluation of novel 2-oxo-1,2-dihydro-3-quinolinecarboxamide derivatives as potent and selective serotonin 5-HT4 receptor agonists

A series of 8′-substituted N-(endo-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolin ecarboxamides were synthesized. The 5-HT4 receptor agonistic activity was evaluated using the isolated guinea pig ileum preparation. Of the compounds synthesized, N-(endo-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1, 2-dihydro-3-quinolinecarboxamide (15a, TS-951) exhibited the most potent serotonin 5-HT4 receptor agonistic activity. This compound had a high affinity for the serotonin 5-HT4 receptor although it had no affinities for other broad spectrum receptors. Furthermore, it remarkably enhanced gastrointestinal motility in conscious fed dogs without unfavorable effects that non-selective serotonin 5-HT4 receptor agonist has. TS-951 may be useful in improving gastrointestinal dysfunction.

A practical procedure for preparation of N-(endo-8-(3-hydroxy)propyl-8-azabicyclo [3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinoline-carboxamide (TS-951)

Effective and convergent process for the preparation of a potent and selective 5-HT4 receptor agonist, the title compound, by reaction of 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid (6) with endo-3-amino-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octane dihydrochloride (20) has been described. Furthermore, this process was developed to pilot plant scale. 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid (6) was prepared from 2-aminobenzyl alcohol (12) in 65.6% overall yield and endo-3-amino-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octane dihydrochloride (20) was prepared from 2,5-dimethoxyfuran (16) in 43.4% overall yield.

Quinolinecarboxylic acid derivatives

Quinolinecarboxylic acid derivatives represented by the following formula: STR1 wherein C is hydroxymethyl, methoxy, ethoxy or morpholinyl, or pharmaceutically acceptable salts thereof exhibit a potent action for stimulating a serotonin 4 receptor. The compounds exhibit an action of enhancing the gastrointestinal motor function to improve the gastrointestinal conditions such as heartburn, anorexia, bowel pain, abdominal distension, etc., accompanied by chronic gastritis, diabetes mellitus or postoperative gastroparesis, and are thus effective for the treatment of gastro-esophagal reflux, intestinal pseudo-obstruction and constipation.