167030-95-7

Basic information

• Product Name: 4-[2-(5-Cyano-6-methoxy-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)-ethyl]-benzoic acid methyl ester
• Synonyms: 4-[2-(5-Cyano-6-methoxy-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)-ethyl]-benzoic acid methyl ester
• CAS NO: 167030-95-7
• Molecular Weight: 314.341
• Mol File: 167030-95-7.mol

Chemical Properties

• CAS DataBase Reference: 4-[2-(5-Cyano-6-methoxy-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)-ethyl]-benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2-(5-Cyano-6-methoxy-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)-ethyl]-benzoic acid methyl ester(167030-95-7)
• EPA Substance Registry System: 4-[2-(5-Cyano-6-methoxy-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)-ethyl]-benzoic acid methyl ester(167030-95-7)

Safety Data

• Hazardous Substances Data: 167030-95-7(Hazardous Substances Data)

Upstream product

• 124-41-4 sodium methylate 
• 109-77-3 malononitrile 
• 213256-74-7 methyl p-(3-methoxycarbonyl-3-butenyl)benzoate 
• 4224-69-5 methyl 2-(bromomethyl)propenoate 
• 67-56-1 methanol 

Downstream Products

• 213256-78-1 methyl 4-[2-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoate 

Relevant articles and documents

Synthesis and biological activity of 7-oxo substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF) and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)

We recently described the syntheses of 12a-c, 4-amino-7-oxo substituted analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid (5-DATHF), and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF), in six steps from commercially available p-substituted methyl benz

Selective reduction of the 7-oxo group in pyrido[2,3d]pyrimidine-4,7- diones: A new synthetic approach to 5,10-dideazatetrahydrofolic acid (DDATHF)

A selective reduction of the carbonyl group at C7 with borane in THF is accomplished for 2,4-diamino-7-oxo and 2-amino-4,7-dioxo substituted pyridopyrimidines (7a-c) and (13a-c) respectively, the ester group remaining unaltered in both cases. The synthesi

Synthesis and biological activity of 4-amino-7-oxo-substituted analogoues of 5-Deaza-5,6,7,8-tetrahydrofolic acid and 5,10-dideaza-5,6,7,8- tetrahydrofolic acid

The 4-amino-7-oxo-substituted analogues of 5-deaza-5,6,7,8- tetrahydrofolic acid (5-DATHF) and 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF) were synthesized as potential antifolates. Treatment of the α,β- unsaturated esters 11a-c, obtained in one synthetic step from commercially available para-substituted benzoates (9a-c) and methyl 2-(bromomethly)- acrylate (10), with malononitrile in NaOMe/MeOH afforded the corresponding pyridones 12a-c. Formation of the pyrido[2,3-d]pyrimidines 13a-c was accomplished upon treatment of 12a-c with guanidine in methanol. After the hydrolysis of the ester group present in 13a-c, the resulting carboxylic acids 14a-c were treated with diethyl cyanophosphonate in Et3N/DMF and coupled with L-glutamic acid dimethyl ester to give 15a-c. Finally, the basic hydrolysis of 15a-c yielded the desired 4-amino-7-oxo-substituted analogues 16a-c in 20-27% overall yield. Compounds 16a-c were tested in vitro against CCRF-CEM leukemia cells. The results obtained indicated that our 4-amino-7- oxo analogues are completely devoid of any activity, the IC50 being higher than 20 μg/mL for all cases except 14c for which a value of 6.7 μg/mL was obtained. These results seem to indicate that 16a-c are inactive precisely due to the presence of the carbonyl group in position C7, the distinctive feature of our synthetic methodology.