Synthesi And Preliminary Bioacticities Test Of Benzene Double Furans,1,3,4-Oxadiazoles And Quinoxalines

This paper focus on preparation of the benzene double furan compound,1,3,4-oxadiazoles compound and quinoxaline compound and the test of the MAO's inhibitory activity,it has selected some compounds with relatively good inhibitory activity.Firstly,starting from the phenyl selenium bromide to prepare the benzene furan skeleton in one step after the intra-molecular condensation;Then synthesis a series of benzene double furan compounds through the interstitial condensation based on this skeleton.Further modify this structure,conduct the nucleophilic substitution reaction with hydrazine hydrate and chloride,and get a series of benzene double furan derivative with hydrazide structure.Secondly,starting from the phenyl selenium bromide to synthesis the a-phenylseleno,thus to replace the propionaldehyde organic selenium reagents,and use this organic selenium to react with hydrazide to produce the corresponding Schiff's base,react with acrtic anhydride to produce the oxdiazoles compound with terminal double bond,further derivatize the organic selenium oxadiazolc compounds with terminal triple bond,cycloaddition reaction with azide and dipolar-cycloaddition reaction with different oxime to produce the organic selenium oxadiazolc derivatives containing the 1,2,3-triazole and the organic selenium oxadiazolc derivatives containing the 5-ester replaced Isoxazoline.Primary amine with different substituent groups is chosen as the beginning material,react with chloroform in the alkali liquor to produce lsocyanide with different substituent groups,then by multicomponent reaction with a-phenylseleno propionaldehyde and o-diaminobenzene under the catalyze of barium cresyisulfonate to produce quinoxaline compound with bioactive molecular selenium.Using fluorescent probe method to do the monoamine oxidase inhibitory activity test to the three kinds of heterocyclic compound.The test result suggests that the benzene double furan compound and quinoxaline compound have relatively higher selectivity to the MAO-A.The compound 1-7-4,1-7-2,1-7-3,1-7-1,1-4-2,1-5-6,3-5-6,3-5-1,3-5-9,3-5-10,3-5-12 has apparent inhibition(IC50<100?M,SI<0.5)to MAO-A,among them the 3-5-12 is the most activated one,and has the highest selectivity.1,3,4-diazoles structure is a very good MAO-B inhibition matrix,the compound 2-6-4,2-6-5,2-6-1,2-5,2-3-12,2-3-2 can serve as the potential monoamine oxidase B enzyme inhibitors(IC50<1.0?M,SI>50),among them,the 2-6-4 is the most activated one and has the highest MAO-B selectivity.