Synthesis and biological properties of 9-(trans-4-hydroxy-2-buten-1-yl)adenine and guanine: open-chain analogs of neplanocin A
- 1 February 1987
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 30 (2) , 437-440
- https://doi.org/10.1021/jm00385a032
Abstract
Alkylation of adenine (5a) or 2-amino-6-chloropurine (5b) with excess trans-1,4-dichloro-2-butene (4), effected by K2CO3 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 HCl. Adenine derivative 2a is a substrate for adenosine deaminase whereas both 2a and 2b exhibit 50% inhibition of the growth of murine leukemia L 1210 cell culture at 1 mM concentration.This publication has 2 references indexed in Scilit:
- Metabolic conversion of Neplanocin A to S-neplanocylmethionine by mouse L 929 cellsBiochemical and Biophysical Research Communications, 1984
- Enzymatic phosphorylation of acyclic nucleoside analogs and correlations with antiherpetic activitiesBiochemical Pharmacology, 1981