Synthesis and biological activities of 5-deaza analogs of aminopterin and folic acid

…, JT Huang, JH Burchenal, KA Watanabe…

Index: Su, Tsann-Long; Huang, Jai-Tung; Burchenal, Joseph H.; Watanabe, Kyoichi A.; Fox, Jack J. Journal of Medicinal Chemistry, 1986 ,  vol. 29,  # 5  p. 709 - 715

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Citation Number: 47

Abstract

N-[p-[[(2, 4-Diaminopyrido [2, 3-d] pyrimidin-6-yl) methyl] amino] benzoyl]-~-glutamic acid (la, 5-deazaaminopterin) and the 5-methyl analogue (lb) were synthesized in 14 steps from 5- cyanouracil (4a) and 5-cyano-6-methyluracil (4b), respectively, by exploitation of the novel pyrimidine to pyrido [2, 3-d] pyrimidine ring transformation reaction. The 5-cyanouracils 4 were treated with chloromethyl methyl ether to the 1, 3-bis (methoxymethyl) uracils (5, ...