Design And Synthesis Of Styrylquinoline Sulfonamide Derivatives

Polydroxylated styrylquinoline derivatives are one of the potential HIV-1 integrase inhibitors with anti-viral activity in cell culture.. The inhibitory molecular basis of styryl quinoline derivatives is to interact with catalytic domain of IN selectively. In the paper, the synthesis of sulfonamide styryl quinoline derivatives is the aim of our research based on the analysis priminary fact of aryl styryl quinoline HIV-1 integrase inhibitors.In the study of quinoline sulfonyl chloride synthesis, we firstly attempted to get quinoline with sulfonic group and then synthesized quinoline sulfonyl chloride.Finally we successfully obtained quinoline sulfonyl chloride just in reaction of quinoline and sulfonic chloride. At the same time, reaction condition was optimized and the yield was improved.In the study of quinoline sulfonylamide derivatives synthesis, three new 8- hydroxy -7- quinoline sulfonylamide derivatives were successfully obtained with substituents, such as–H,-Cl,-CH₃. ¹H NMR and MS analysis reveals not only 8- hydroxy is substituted by acetyl group ,but also the hydrogen atom of 7-sulfonylamide is replaced by acetyl group.The detail synthesis of styrylquinoline sulfonamide derivatives have been investigated and 13 new styrylquinoline sulfonamide derivatives were obtained with substituents, such as -H, -Cl, -Br, -OCH₃, -OH,-OAc. The above compounds were identified by ¹H NMR,¹³C NMR,IR and MS. we surprisedly found that the conversion of 4-hydroxy benzaldehyde to its corresponding 1,1-diacetates could be catalyzed by weak organic acid.The above 8- acetyl-7- sulfonamide styrylquinoline derivatives were hydrolyzed in weak basic condition to give 12 8- hydroxy -7- quinoline sulfonylamide derivatives.All of the new compounds were identified by 1H NMR,13CNMR,IR and MS.