Controllable selective synthesis of a polymerizable prodrug of cytarabine by enzymatic and chemical methods |
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Authors: | Wang Na Chen Zhi Chun Lu De Shui Lin Xian Fu |
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Institution: | Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China. |
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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. |
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