engleski

Green Synthesis And Antitumor Evaluations Of Novel Racemic And Optically Pure Aryl-Substituted Purine Bioisosteres

Enzymes, receptors, and other binding molecules in biological processes can recognize enantiomers as different molecular entities, consequently, using a single pure enantiomer instead of a racemate can enhance the effectiveness and safety of the treatment [1]. The method for the synthesis of enantiopure or highly enantio-enriched compounds is asymmetric organometallic catalysis, which has been recently replaced by biocatalysis. An important example of enzymatic biocatalysis is the nucleophilic opening of epoxy rings with sodium azide catalysed by halohydrin dehalogenase (HHDHs) [2]. Enantiomerically pure β-azido alcohols are very important building blocks in the synthesis of 1, 2, 3-triazole derivatives [3]. As part of our research on developing multi-target small molecule anticancer agents, we designed, synthesized, and biologically evaluated a series of 66 novel hydroxyl aryl-substituted N-heterocycle derivatives. A series of 50 racemic and 16 optical pure 1, 4-disubstituted 1, 2, 3-triazoles were synthesized by the copper(I)-catalyzed Huisgen 1, 3-dipolar cycloaddition of terminal alkynyl derivatives of purine and purine isosteres and aryl-substituted 1, 2-azido alcohols under environmentally friendly ultrasound irradiation. The synthesis and antitumor effects of all derivatives will be presented.

purine, azido alcohols, enantiomers, halohydrin dehalogenase

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