Pál Csuka, Z. Boros, L. Őrfi
Jul 15, 2015
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Ethyl and isopropyl cyanoacetates were tested as acylating agents in the kinetic resolution of racemic 1-phenylethanamine rac - 1 catalyzed by lipase B from Candida antarctica . The best conversion combined with high enantioselectivity was achieved with ethyl cyanoacetate 2a as the acylating agent and immobilized lipase B from Candida antarctica ( Ca LB N435) as the biocatalyst. Enantiomers of the amides ( R )- 3 and ( S )- 3 were obtained with high enantiopurity (ee >98%) by lipase-catalyzed kinetic resolution and by chemical conversion of the residual ( S )- 1 , respectively. The amides were reacted with various aromatic aldehydes 4a – c , e in Knoevenagel condensation to yield Tyrphostins rac- 5a – c , e , ( R )- 5a – c , e and ( S )- 5a – c , e , which were tested as protein tyrosine kinase inhibitors on human cancer cell lines HCT 116, A549, PC9, PC9ER, Jurkat, and MV4-11. Although some of the novel Tyrphostins exhibited weak biological activities (EC 50 ∼6–60 μM), none of them proved to have a significant effect on the growth of the investigated cell lines.