Synthesis And Biological Activities Of 2-(4-methoxyphenyl)-4-methyl-1,3-selenazole-5-heterocyclic Derivatives/Docking Compounds Of 1,3,5-triazine And 1,2,4-triazole Derivatives

The syntheses and applications of selenium-containing heterocyclic compounds,1,3,5-triazine and 1,2,4-triazole derivatives were reviewed.Twenty-two 1,3-selenazole heterocyclic derivatives and fourteen docking compounds of 1,3,5-triazine and 1,2,4-triazole derivatives were first designed and synthesized.The structure of target product was confirmed and the biological activities were evaluated.The details were as follows:In order to explore the synthetic strategies of multi-heterocyclic compounds based on,substituted 1,3-selenazole,twenty-two novel multi-heterocyclic molecules(SAZ1-22)were first designed and synthesized.The structures of the target molecules were confirmed by IR,NMR,and HRMS.New ideas and methods were developed for the construction of multi-heterocyclic molecules containing selenazole unit,and lay the foundation for anti-tumor active selection.Owing to the excellent biological activities of 1,3,5-triazine and 1,2,4-triazole,fourteen docking compounds(TZS 1-14)of 1,3,5-triazine and 1,2,4-triazole derivatives was first designed and synthesized through simple and efficient method.First,two single substituted intermediates(1a,1b)were afforded through the reaction of 1,3,5-triazine with amine derivatives.Second,5-n-pentyl-4-amino-1,2,4-triazole-3-thiol(2)was obtained using melting method by the reaction of n-pentanoic acid with dithiocarbohydrazone,and schiff bases(3)were synthesized by the reaction of compound 2 with different aldehydes.Finally,The target molecules were generated through double coupling reactions of 1 with 3 with overal yield 65%-80%.The structures of TZS1-14 were characterized by IR,NMR,and HRMS.The inhibition activities of SAZ1-22 and TZS1-14 against Cdc25B was evaluated for the first time.The results showed that there are twenty compounds which its inhibition rates were more than 50%.This result indicated that the novel structure exhibited good inhibition activity against Cdc25B.The IC50 values of SAZ-1,SAZ-9,SAZ-13,SAZ-14 and SAZ-19 were 1.82±0.65,1.46±0.45,1.75±0.39,1.25±0.26 and 1.46±0.19 μg/mL,where the IC50 value of positive reference sodium orthovanadate was 1.86±0.24μg/mL.Similarly,the IC50 of TZS-6、TZS-13、TZS-14 were 1.04±0.26,1.37±0.15 and 1.71±0.56 pg/mL which were also higher than the positive reference sodium orthovanadate.These results indicated that the target molecules could be used as a potential inhibitor of Cdc25B,maybe become the leading compounds of anti-tumor drug.The plant growth regulating and herbicidal activities were evaluated using the second kind compounds TZS1-14.The cytokinin activity showed that most compounds behaved a satisfactory promoting activity unless TZS-13.Ten products showed A level promotion effect.Notably,TZS-4 showed a optimal promoting activity up to 75.3%.The results of auxin activity tests indicated that the promoting activity of TZS-5 and TZS-12 were up to B level,and others showed C level.The herbicidal activities of most compounds were better than 40%,in which TZS-3 was up to 89.2%and it was expected to be an excellent herbicide.