Purines. XXXVI. : Fission and Reclosure of the Adenine Ring in 3,9-Disubstituted Adenines : Effects of Substituents
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概要
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In order to investigate the effects of the N(3)- and N(9)-substituents in 3,9-disubstituted adenines on the stability of the adenine ring, the equilibrium constants and the rates of ring opening and cyclization for the equilibria between the 3,9-disubstituted adenines IVa-l and the N-alkylformamidoimidazoles Va-l in H_2O at pH 8.98 and 25 ℃ have been measured. A bulky substituent at the 3-position of IV has been found to retard the ring opening leading to V, whereas an electron-withdrawing group at the 3- or 9-position accelerates it. A bulky alkyl group on the formamido nitrogen of V markedly retards the cyclization leading to IV, favoring the ring-opened form in the equilibrated mixture. Syntheses of 3-isopropyl-9-methyladenine perchlorate (IVc) and 3-(4-methoxybenzyl)-9-methyladenine perchlorate (IVe), required for the kinetic study as substrates, are also described.
- 公益社団法人日本薬学会の論文
- 1989-12-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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中坂 剛志
Faculty of Pharmaceutical Sciences, Kanazawa University
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藤井 澄三
Shinshu Univ. Nagano Jpn
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中坂 剛志
Faculty Of Pharmaceutical Sciences Kanazawa University
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