Purines. LII. Synthesis and biological evaluation of 8-methylguanine 7-oxide and its 9-arylmethyl derivatives.
The synthesis of 8-methylguanine 7-oxide (3) was accomplished via a "phenacylamine route", which started from condensation of alpha-(4-methoxybenzylamino)propiophenone (6), prepared by coupling of alpha-bromopropiophenone (4) and 4-methoxybenzylamine (5), with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone (7) and proceeded through cyclization of the resulting phenacylaminopyrimidinone (8) and removal of the 4-methoxybenzyl group. The N-oxide 3 and its 9-arylmethyl derivatives 9 and 11 showed only very weak antileukemic activity and no antimicrobial activity.
Ogawa
K
K
Research Laboratories, Ikeda Mohando Co., Ltd., Toyama, Japan.
Nishii
M
M
Inagaki
J
J
Nohara
F
F
Saito
T
T
Itaya
T
T
Fujii
T
T
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D008745:Methylation; D051379:Mice; D011687:Purines / Q000138:chemical synthesis* / Q000494:pharmacology
D000903:Antibiotics, Antineoplastic; D011687:Purines; C076914:8-methylguanine 7-oxide; D006147:Guanine