C-aryl glycosides are an important kind of carbohydrate derivatives for drug discovery,due to their distinctive attributes of resistance to hydrolysis from enzymes.Herein,C-aryl glycosylation was established for the s...C-aryl glycosides are an important kind of carbohydrate derivatives for drug discovery,due to their distinctive attributes of resistance to hydrolysis from enzymes.Herein,C-aryl glycosylation was established for the synthesis of 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process,featured with sulfonium-tethered[3,3]-sigmatropic rearrangement between sulfoxide glycals and phenols.This protocol offers a broad substrate scope with diverse glycosyl and phenols.Dapagliflozin,Empagliflozin,and Ipragliflozin analogs were straightforward achieved,respectively.展开更多
The preparation of several functionalized furan derivatives and attempts to transform them into a derivative containing 6H-furo[3,4-b]furanone skeleton towards the construction of naphtho[2,3-b] furan are described. A...The preparation of several functionalized furan derivatives and attempts to transform them into a derivative containing 6H-furo[3,4-b]furanone skeleton towards the construction of naphtho[2,3-b] furan are described. Attempted Pummerer reaction of a furan sulfoxide derivative produced four interesting furan derivatives. Base promoted annulation between methyl 2-(phenylsulfinylmethyl)-3-furoate and 2-cyclohexenone proceeded to give dihydro naphtho[2,3-b]furanone derivative in a regiospecific manner.展开更多
Main observation and conclusion The reaction of 2-alkynylanisoles/sulfides with SOCl_(2) and DMSO was conducted to conveniently furnish the biologically interesting 3-(methylthio)-benzo[b]furans/thiophenes via intramo...Main observation and conclusion The reaction of 2-alkynylanisoles/sulfides with SOCl_(2) and DMSO was conducted to conveniently furnish the biologically interesting 3-(methylthio)-benzo[b]furans/thiophenes via intramolecular cyclization.DMSO acts as a solvent as well as a sulfur source and can also be replaced with DMSO-d_(6),enabling the incorporation of the SCD3 moiety of DMSO-d_(6) to the 3-position of the heterocyclic frameworks.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
基金The authors are grateful for financial support provided by NSFC(22125103and21971065)STCSM(22JC1401000,20xD1421500 and 20JC1416800)the Fundamental Research FundsfortheCentral Universities.
文摘C-aryl glycosides are an important kind of carbohydrate derivatives for drug discovery,due to their distinctive attributes of resistance to hydrolysis from enzymes.Herein,C-aryl glycosylation was established for the synthesis of 2-sulfur C-aryl glycals and 1,2-dihydrobenzofuran-fused C-aryl glycosides via interrupted Pummerer process,featured with sulfonium-tethered[3,3]-sigmatropic rearrangement between sulfoxide glycals and phenols.This protocol offers a broad substrate scope with diverse glycosyl and phenols.Dapagliflozin,Empagliflozin,and Ipragliflozin analogs were straightforward achieved,respectively.
文摘The preparation of several functionalized furan derivatives and attempts to transform them into a derivative containing 6H-furo[3,4-b]furanone skeleton towards the construction of naphtho[2,3-b] furan are described. Attempted Pummerer reaction of a furan sulfoxide derivative produced four interesting furan derivatives. Base promoted annulation between methyl 2-(phenylsulfinylmethyl)-3-furoate and 2-cyclohexenone proceeded to give dihydro naphtho[2,3-b]furanone derivative in a regiospecific manner.
基金We acknowledge the National Natural Science Foundation of China(No.21472136)for financial support.
文摘Main observation and conclusion The reaction of 2-alkynylanisoles/sulfides with SOCl_(2) and DMSO was conducted to conveniently furnish the biologically interesting 3-(methylthio)-benzo[b]furans/thiophenes via intramolecular cyclization.DMSO acts as a solvent as well as a sulfur source and can also be replaced with DMSO-d_(6),enabling the incorporation of the SCD3 moiety of DMSO-d_(6) to the 3-position of the heterocyclic frameworks.
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.
