213256-78-1

Basic information

• Product Name: methyl 4-[2-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoate
• Synonyms: methyl 4-[2-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoate
• CAS NO: 213256-78-1
• Molecular Weight: 341.37
• Mol File: 213256-78-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 4-[2-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-[2-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoate(213256-78-1)
• EPA Substance Registry System: methyl 4-[2-(2,4-diamino-7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoate(213256-78-1)

Safety Data

• Hazardous Substances Data: 213256-78-1(Hazardous Substances Data)

Upstream product

• 113-00-8 guanidine nitrate 
• 167030-95-7 4-[2-(5-Cyano-6-methoxy-2-oxo-1,2,3,4-tetrahydro-pyridin-3-yl)-ethyl]-benzoic acid methyl ester 
• 357400-76-1 methyl 4-(5,5-dicyano-3-methoxycarbonylpentyl)benzoate 
• 213256-74-7 methyl p-(3-methoxycarbonyl-3-butenyl)benzoate 

Downstream Products

• 213256-87-2 (S)-2-{4-[2-(2,4-Diamino-7-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoylamino}-pentanedioic acid dimethyl ester 
• 213256-82-7 4-[2-(2,4-Diamino-7-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-benzoic acid 

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

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.