158577-01-6

Basic information

• Product Name: 1-Isopropyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid
• Synonyms: 1-Isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylicacid
• CAS NO: 158577-01-6
• Molecular Formula: C₁₃H₁₃NO₃
• Molecular Weight: 231.24722
• Mol File: 158577-01-6.mol

Chemical Properties

• Melting Point: 178-180 °C
• Boiling Point: 354.8±41.0 °C(Predicted)
• Appearance: /
• Density: 1.288±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.35±0.20(Predicted)
• CAS DataBase Reference: 1-Isopropyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Isopropyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid(158577-01-6)
• EPA Substance Registry System: 1-Isopropyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid(158577-01-6)

Safety Data

• Hazardous Substances Data: 158577-01-6(Hazardous Substances Data)

Usage

Uses

As of now, there are no widely recognized applications for 1-Isopropyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid. However, given its unique structure and chemical properties, it may have potential uses in various fields once further research and development are conducted. Possible applications could include:
Used in Research and Development:
1-Isopropyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid is used as a research compound for exploring its chemical properties and potential applications in various industries. Its unique structure and functional groups may offer insights into new chemical reactions or processes.

Upstream product

• 103718-15-6 2-(isopropylamino)benzaldehyde 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 75-31-0 isopropylamine 
• 64-19-7 acetic acid 
• 107-15-3 ethylenediamine 
• 110-89-4 piperidine 
• 552-89-6 2-nitro-benzaldehyde 
• 85870-47-9 1,2-dihydro-2-oxo-3-quinolinecarboxylic acid,ethyl ester 
• 17422-56-9 diethyl 2-(2-nitrobenzylidene)malonate 
• 158577-00-5 ethyl 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylate 
• 2033-24-1 cycl-isopropylidene malonate 
• 106898-71-9 2-isopropylaminobenzyl alcohol 
• 5226-51-7 2,2-dimethyl-1,4-dihydro-2H-3,1-benzoxazine 
• 5344-90-1 2-Aminobenzyl alcohol 

Downstream Products

• 866933-46-2 Velusetrag 
• 174486-39-6 endo-N-(8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide 
• 174486-39-6 N-(endo-8-(3-hydroxy)propyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide 

Relevant articles and documents

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

A series of N-azabicycloalkyl-1-alkyl-2-oxo-1,2-dihydro-3-quinolinecarboxamides were synthesized and tested for serotonin 5-HT4 receptor-stimulating effects in the regulation of electrically-evoked contraction in guinea pig muscle. Among them, N-azabicycloalkyl-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide (8c, 9c, 10c, 11c, 12c) exhibited potent serotonin 5-HT4 receptor-stimulating activity. The most potent compound, N-(endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3 -quinolinecarboxamide (8c, ED50= 36.3 nM), was seven times as active as cisapride, while 8c had no affinity for 5-HT,1A, 5-HT1D, D2, muscarinic M2 or muscarinic M3 receptors even at 10 μM. Compound 8c stimulated digestive tract motility in conscious fed dogs (1.0 mg/kg p.o.).

Aqueous synthesis of N-phenyl/alkyl-2-quinolinone-3-carboxylic acids from coumarin-3-carboxylic acids

An efficient, ecofriendly aqueous synthesis of aromatic/aliphatic amines with coumarin-3-carboxylic acid in a one pot reaction in a sealed tube or InCl3/ H2O in open vessel to afford N-phenyl/alkyl-2-quinolinones is achieved. This method provides high yield of products in shorter time, making it a useful process for the synthesis of structurally diversified 2-quinolinones from corresponding coumarins. Copyright

Prokinetic agent for bowel preparation

The invention provides methods of bowel preparation before a diagnostic, surgical or therapeutic procedure, in particular, bowel preparation before a colonoscopy procedure, using a 5-HT4 receptor agonist as a prokinetic agent.

Quinolinone-carboxamide compounds

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

5-HT4 receptor agonist compounds

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

Quinolinone compounds as 5-HT4 receptor agonists

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

Crystalline form of a quinolinone-carboxamide compound

The invention provides a crystalline hydrochloride salt of 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid {(1S,3R,5R)-8-[(R)-2-hydroxy-3-(methanesulfonyl-methyl-amino)propyl]-8-azabicyclo[3.2.1]oct-3-yl}amide or a solvate thereof. The invention also provides pharmaceutical compositions comprising such crystalline salt forms, methods of using such crystalline salt forms to treat diseases associated with 5-HT4 receptor activity, and processes useful for preparing such crystalline salt forms.

Quinolinone-carboxamide compounds as 5-HT4 receptor agonists

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

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.