82855-85-4

Basic information

• Product Name: diethyl N-(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropyrido[3,2-d]pyrimidin-6-yl)methyl]amino}benzoyl)glutamate
• CAS NO: 82855-85-4
• Molecular Formula: C₂₄H₃₂N₆O₆
• Molecular Weight: 500.5475
• Mol File: 82855-85-4.mol
• Article Data: 2

Chemical Properties

• Density: 1.41g/cm³
• Refractive Index: 1.647
• CAS DataBase Reference: diethyl N-(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropyrido[3,2-d]pyrimidin-6-yl)methyl]amino}benzoyl)glutamate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl N-(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropyrido[3,2-d]pyrimidin-6-yl)methyl]amino}benzoyl)glutamate(82855-85-4)
• EPA Substance Registry System: diethyl N-(4-{[(2-amino-4-oxo-1,4,5,6,7,8-hexahydropyrido[3,2-d]pyrimidin-6-yl)methyl]amino}benzoyl)glutamate(82855-85-4)

Safety Data

• Hazardous Substances Data: 82855-85-4(Hazardous Substances Data)

Upstream product

• 82855-87-6 diethyl N¹⁰-nitroso-8-deazafolate 
• 76807-65-3 diethyl 8-deazafolate 
• 76807-65-3 Diethyl 8-Deazafolic Acid 

Downstream Products

• 88543-93-5 diethyl N-<4-<<<2-amino-3,4,5,6,7,8-hexahydro-4-oxo-5-<(2'-deoxy-3'-O-acetyluridin-5-yl)methyl>pyrido<3,2-d>pyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamate 5'-(trichloroethyl methyl phosphate) 
• 88543-92-4 diethyl N-<4-<<<2-amino-3,4,5,6,7,8-hexahydro-4-oxo-5-<(2'-deoxy-3'-O-acetyluridin-5-yl)methyl>pyrido<3,2-d>pyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamate 5'- 
• 82855-86-5 2-[4-({5-[1-((2R,4S,5R)-4-Acetoxy-5-acetoxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl]-2-amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[3,2-d]pyrimidin-6-ylmethyl}-amino)-benzoylamino]-pentanedioic acid diethyl ester 
• 82855-86-5 diethyl N-<4-<<<2-amino-3,4,5,6,7,8-hexahydro-4-oxo-5-<(3',5'-diacetyl-2'-deoxyuridin-5-yl)methyl>pyrido<3,2-d>pyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamate 
• 82870-62-0 N-<4-<<<2-amino-3,4,5,6,7,8-hexahydro-4-oxo-5-<(2'-deoxyuridin-5-yl)methyl>pyrido<3,2-d>pyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamic acid 
• 92008-00-9 N-<4-<<<2-amino-3,4,5,6,7,8-hexahydro-4-oxo-5-<(2'-deoxyuridin-5-yl)methyl>pyrido<3,2-d>pyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamic acid 5'-monophosphate 
• 82855-89-8 diethyl N-nitroso-N-<4-<<<2-amino-3,4,5,6,7,8-hexahydro-4-oxo-5-<(3',5'-diacetyl-2'-deoxyuridin-5-yl)methyl>pyrido<3,2-d>pyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamate 
• 82870-62-0 N-<4-<<(2-amino-3,4,5,6,7,8-hexahydro-4-oxo-5-(2'-deoxyuridin-5-yl)methylpyrido<3,2-d>pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 82855-89-8 C₃₈H₄₇N₉O₁₄ 

Relevant articles and documents

A Potent Multisubstrate Analogue Inhibitor of Human Thymidylate Synthetase

The synthesis of an 8-deazafolate analogue of the intermediate in the methylation of 2'-deoxyuridylate is described.Alkylation of diethyl 5,6,7,8-tetrahydro-8-deazafolate with 3'-O-acetyl-5-(bromomethyl)-2'-deoxyuridine 5'-, followed by removal of the trichloroethyl groups with a Zn/Cu couple and mild saponification, gave the target inhibitor N-pyridopyrimidin-6-yl>methyl>amino>benzoyl>-L-glutamic acid 5'-monophosphate.The free nucleoside and the 5'-(methyl phosphate) diester were similary prepared.Each of these reactions yielded a pair of diastereoisomers about C-6 of the reduced deazafolate in approximately a 1:1 ratio.These diastereomeric mixtures were evaluated as inhibitors of thymidylate synthetase derived from human tumor (HeLa) cells.The 5'-monophosphate was a potent inhibitor, competitive with respect to both 2'-deoxyuridylate (Ki = 0.06 μM) and tetrahydrofolate (Ki = 0.25 μM).In contrast, the nucleoside and the nucleotide methyl ester were poorer inhibitors by more than 3 orders of magnitude, attesting to the importance of the anionic function at the nucleoside 5'-position in the affinity of an inhibitor for the enzyme active site.