Abstract:

Amino acids and their derivatives have some applications in coagulant/anticoagulant activities. L-phenylalanine was used as starting material and sulfonated for introducing sulfonic acid group, and then dehydrated with methanol, ethanol, propanol, isopropanol, and n-butanol to synthesize six derivatives L1~L6. Six novel sulfonic acid esterified derivatives of L-phenylalanine L1~L6 were synthesized in one pot in order to obtain strong physiological activity for potential coagulant/anticoagulant drugs. The structures of the six derivatives were characterized by mass spectrometry and nuclear magnetic resonance. The yield by this synthetic method is high(78%~95%) and the post-treatment is simple for the synthesis of such derivatives. Four items of blood coagulation of derivatives show that anticoagulant and pro-coagulant effects are the result of the interaction of endogenous and extrinsic coagulation pathways. The plasma re-calcification time shows that the derivatives have certain anticoagulant activity, and their anticoagulant effects are changed with the concentration, but the anticoagulant effect does not have such a regular relationship with the increase of R chain. The anticoagulant activity of the derivative is mainly affected by sulfonic and ester groups, so the introduction of sulfonic acid and ester groups can be considered for designing and synthesizing antithrombotic compounds.

Key words: L-phenylalanine, synthesis, ester derivatives, anti/pro-coagulant activity