The Synthesis And Modification Of1,4-dihydropyridine Derivatives

1，4-Dihydropyridine (DHP) is a class of compounds with good biologicalactivity and pharmacological effects，its derivatives has been studied because oftheir potential applications in treatment of cardiovascular diseases. Twenty1,4-dihydropyridine derivatives has been synthesized in this paper, ten of them withnovel structures have not been reported. While in the synthesis of dihydropyridines,we got five Schiff base which have not been reported. All of the novel compounds hasbeen confirmed by1H NMR、13C NMR、IR、MS.The main content of this paper includes the following three parts:1、 Two1,4-dihydropyridines were synthesized through classical Hantzschreaction with aromatic aldehyde、β-keto ester and ammonia as material. These twocompounds were hydrolyzed in an alkaline environment subjected to dihydropyridineacids. Finally, the seven target compounds were synthesized via two-componentcondensation reaction of1,4-dihydropyridine acids and hydroxyl-substitutedchalcone.Because of both dihydropyridine and chalcone had anti-oxidant andphotoluminescence activities, the anti-oxidant and photoluminescence activities ofthese compounds were also been investigated.2、N-substituted dihydropyridine compounds did not showed good effect on theanti-hypertensive, but it had other physiological activity and the photosensitiveactivity, we also investigate the synthesis of N-substituted dihydropyridinederivatives. When we tried to use5-phenyl-1,3,4-thiadiazol-2-amine as source ofammonia to synthesize N-5-phenyl-1,3,4-thiadiazol-substituted dihydropyridinederivatives, the reaction was failed, but we got five new Schiff base which had notbeen reported. In addition, for failed to obtained the target compounds, we discussedthe mechanism in this paper.3、The structure-activity relationships of DHPs have indicated that the groups in4-positions are very important for pharmacological effects. So, C4of dihydropyridinederivatives were modified. Diphenyl imine were introduced into the C4position of1,4-dihydropyridines. Finally, three C4Diphenyl imine-substituted dihydropyridineswere synthesized. In addition, the mechanisms of three-steps synthesis ofdihydropydines have also been discussed in this paper.