1 Introduction Heteroatom-stabilized carbenium ions have been widely recognized as potential electrophilic reagents.However,in contrast with the extensive works on thionium ion series,the highly labile character of se...1 Introduction Heteroatom-stabilized carbenium ions have been widely recognized as potential electrophilic reagents.However,in contrast with the extensive works on thionium ion series,the highly labile character of selenoxide functionalities has caused serious limitation in the synthetic use in spite of their wide potentiality as synthetic equivalents of electrophilic selonium ions.In this paper,novel generation of selonium ions and the synthetic uses of the species for Pummerer-typeα-functionalization and for cycloaddition by using the novel dienophilic behavior ofπ-conjugated selonium cations.展开更多
A series of 2-aryl-3-(4,5,6-trimethylpyrimidin-2-yl)thiazolidin-4-ones(1a–1c)and their derivatives bearing a lipophilic substituent,like acetoxy group(3a–3c),propionyloxy group(4a–4c),methyl(5d and 5e)at C-5 on thi...A series of 2-aryl-3-(4,5,6-trimethylpyrimidin-2-yl)thiazolidin-4-ones(1a–1c)and their derivatives bearing a lipophilic substituent,like acetoxy group(3a–3c),propionyloxy group(4a–4c),methyl(5d and 5e)at C-5 on thiazolidin-4-one ring were designed,synthesized and evaluated for their HIV-RT inhibitory activity.Using self-catalyzed Pummerer reaction,compounds 3a–3c and 4a–4c were obtained in good yield(63.1%–75.2%).Prelimin-ary anti-HIV-RT test of these derivatives indicated that compounds 1a–1c,4b(propionyloxy group at C-5)showed moderate HIV-RT inhibitory activity and com-pounds 5d and 5e with methyl at C-5 showed a weak HIV-RT inhibitory activity.Structure activity relationship analysis suggested that the substituted groups on C-5 would be unfavorable to anti-HIV-RT activity and that the steric effect might play a critical role in the anti-HIV RT activity.展开更多
文摘1 Introduction Heteroatom-stabilized carbenium ions have been widely recognized as potential electrophilic reagents.However,in contrast with the extensive works on thionium ion series,the highly labile character of selenoxide functionalities has caused serious limitation in the synthetic use in spite of their wide potentiality as synthetic equivalents of electrophilic selonium ions.In this paper,novel generation of selonium ions and the synthetic uses of the species for Pummerer-typeα-functionalization and for cycloaddition by using the novel dienophilic behavior ofπ-conjugated selonium cations.
基金financial support from the National Natural Science Foundation of China(Grant No.20672027)the Natural Science Foundation of Hebei Province(2008000588)are gratefully acknowledged.
文摘A series of 2-aryl-3-(4,5,6-trimethylpyrimidin-2-yl)thiazolidin-4-ones(1a–1c)and their derivatives bearing a lipophilic substituent,like acetoxy group(3a–3c),propionyloxy group(4a–4c),methyl(5d and 5e)at C-5 on thiazolidin-4-one ring were designed,synthesized and evaluated for their HIV-RT inhibitory activity.Using self-catalyzed Pummerer reaction,compounds 3a–3c and 4a–4c were obtained in good yield(63.1%–75.2%).Prelimin-ary anti-HIV-RT test of these derivatives indicated that compounds 1a–1c,4b(propionyloxy group at C-5)showed moderate HIV-RT inhibitory activity and com-pounds 5d and 5e with methyl at C-5 showed a weak HIV-RT inhibitory activity.Structure activity relationship analysis suggested that the substituted groups on C-5 would be unfavorable to anti-HIV-RT activity and that the steric effect might play a critical role in the anti-HIV RT activity.
