220545-72-2

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 220545-64-2 (E)-diethyl N-<4-<4-(5-formyl-4-methoxy-2-pivaloylaminopyrimidin-4-yl)-N-4-methoxybenzylamino>-1-butenyl>benzoyl-L-glutamate 
• 220545-83-5 6-(N-3-butynylamino-N-4-methoxybenzyl)-5-formyl-4-methoxy-2-pivaloylaminopyrimidine 
• 220545-62-0 6-(N-3-butenylamino-N-4-methoxybenzyl)-5-formyl-4-methoxy-2-pivaloylaminopyrimidine 
• 220545-79-9 2-amino-6-(N-3-butynylamino-N-4-methoxybenzyl)-4-chloro-5-formylpyrimidine 
• 220545-81-3 2-amino-6-(N-3-butynylamino-N-4-methoxybenzyl)-5-formyl-4-methoxypyrimidine 
• 146980-79-2 N-(4-methoxybenzyl)-4-amino-1-butyne 

Downstream Products

• 56277-36-2 diethyl 4-formylbenzoyl-L-glutamate 
• 220545-92-6 diethyl 4-<(10-methoxy-8-pivaloylamino)-3,4,5,6-tetrahydro-(6H)-isoxazolino<3,4-d>pyrimido<4,5-b>azepin-3-yl>benzoyl-L-glutamate 
• 220545-74-4 diethyl 4-<(10(9H)-oxo-8-pivaloylamino)-3,4,5,6-tetrahydro-(6H)-isoxazolino<3,4-d>pyrimido<4,5-b>azepin-3-yl>benzoyl-L-glutamate 

Relevant academic research and scientific papers

Synthesis of N-{[4-(2-amino-4(3H)-oxo-5,6,7,8-tetrahydro-(9H)- pyrimido[4,5-b]-azepin-6-yl)methyl]benzoyl}-L-glutamic acid and two of its conformationally-restricted analogs

Synthesis of the titled tetrahydropyrimidoazepine-based folate (6a) is described using a regiospecific γ-alkylation reaction between the dienolate generated from 3-carboethoxy-N-2,4-dimethoxybenzyl-1,5,6,7-tetrahydro-(1H)- azepin-2-one (33) and methyl 4-formylbenzoate, as the key step. The isoxazolinopyrimidoazepine and isoxazolopyrimidoazepine-based folates (7a and 8a respectively) were also prepared (via intramolecular 1,3-dipolar cycloaddition chemistry) as conformationally-restricted analogs of 6a. All three compounds were prepared as potential antitumor agents based on the known, structurally related, antitumor agent 5,10-dideaza-5,6,7,8- tetrahydrofolic acid (DDATHF). Both 7a and 8a were inactive in the human colon carcinoma (GC3c1) cell culture assay. Compound 6a, however, was weakly active (IC50 = 2.0 μM) in the above assay.