Synthesis and biological properties of 9-(trans-4-hydroxy-2-buten-1-yl) adenine and guanine: open-chain analogs of neplanocin A

S Phadtare, J Zemlicka

Index: Phadtare, Shashikant; Zemlicka, Jiri Journal of Medicinal Chemistry, 1987 , vol. 30, # 2 p. 437 - 440

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Citation Number: 33

Abstract

Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1, 4-dichloro-2- butene(4), effected by KzC03 in dimethyl sulfoxide or tetra-n-butylammonium fluoride in tetrahydrofuran, led in 90-95% regioselectivity to 9-alkylpurines 6a and 6b. The title compounds 2a and 2b were obtained by refluxing intermediates 6a and 6b in 0.1 M NaOH or HC1. Adenine derivative 2a is a substrate for adenosine deaminase whereas both 2a ...