Collection of Czechoslovak Chemical Communications p. 1109 - 1125 (2000)
Update date:2022-08-02
Topics:
Meszarosova, Katerina
Holy, Antonin
Masojidkova, Milena
9-(4-Hydroxybutyl)adenine (10) was obtained by reaction of adenine with 4-[(2-tetrahydropyran-2-yl)oxy]butyl chloride (7) in the presence of DBU. 8-Bromo-9-(4-hydroxybutyl)adenine (13) was prepared by bromination of 10 or by alkylation of 8-bromoadenine (11) with 4-bromoethyl acetate followed by methanolysis. Tosylation of compound 13 afforded the 4-tosyloxy derivative 15 which gave on heating with methylamine or cyclopropylamine 6-methyl-(17a) or 6-cyclopropyl-7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17b), while the reaction with hydrazine afforded 7,8,9,10-tetrahydro-6H-[1,3]diazepino-[1,2-e]purine-4,6-diamine (17d). Treatment of compound 13 with thionyl chloride gave 9-(4-chlorobutyl)-8-chloroadenine (18) as the main product which was transformed to 17b, 6-propyl-7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17c) or 7,8,9,10-tetrahydro-6H-[1,3]diazepino[1,2-e]purin-4-amine (17e) by reaction with cyclopropylamine, propylamine or ammonia, respectively. Compound 17e was quite stable both in acid and alkaline solutions, at room temperature or at 90 °C. Compound 13 was converted to 9-(4-hydroxybutyl)-8-methylaminoadenine (19) by reaction with methylamine. Compound 19 failed to undergo intramolecular cyclization to diazepine 17a on treatment with diphenyl carbonate, bis(4-nitrophenyl) carbonate or 1,1′-carbonyldiimidazole.
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Doi:10.1021/om000618h
(2000)Doi:10.1023/A:1012442205046
(2001)Doi:10.1039/b005110l
(2000)Doi:10.1007/BF00480656
()Doi:10.1016/j.bmc.2006.09.017
(2006)Doi:10.1016/S0022-328X(99)00761-5
(2000)