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Controllable selective synthesis of a polymerizable prodrug of cytarabine by enzymatic and chemical methods.

Abstract：

:Selectivity of enzymatic and chemical methods for transesterifications of cytarabine with divinyl dicarboxylates was described. Catalysis by lipase acrylic resin from Candida antarctica (CAL-B) in acetone facilitated the single step synthesis of polymerizable 5'-O-acyl cytarabine derivatives in high yields, while the use of alkaline protease from Bacillus subtilis (subtilisin) in pyridine afforded the mixture products of 5'-O-acyl and 4-N-acyl cytarabine derivatives. Interestingly, polymerizable 4-N-acyl cytarabine vinyl derivatives can be selectively prepared by chemical transesterification in dioxane. The obtained series of cytarabine derivatives would be useful for a significant monomer for a polymeric anticancer drug.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Wang N,Chen ZC,Lu DS,Lin XF

doi

10.1016/j.bmcl.2005.06.011

subject

Has Abstract

pub_date

2005-09-15 00:00:00

pages

4064-7

issue

18

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(05)00759-6

journal_volume

15

pub_type

杂志文章

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