Synthesis, reactions and conformational analysis of 5-arylidene-2-thiohydantoins as potential antiviral agents

被引:19
作者
Khodair, AI [1 ]
El-Barbary, AA
Abbas, YA
Imam, DR
机构
[1] Tanta Univ, Fac Educ, Dept Chem, Kafr Al Sheikh, Egypt
[2] Tanta Univ, Fac Sci, Dept Chem, Tanta, Egypt
关键词
D O I
10.1080/10426500108040603
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
(Z)-5-Arylidene-1-(4-methylphenylsulfonyl)-2-thiohydantoins 5a,b were synthesized from the direct condensation of the aromatic aldehydes 4a,b with 1-(4-methylphenylsulfonyl)-2-thiohydantoins 3a,b. Compounds 5a,b were coupled with 2'-deoxy-3',5'-di(4-methylbenzoyl)-alpha -D-erythro-pentofuranosyl chloride 6 under alkaline conditions to afford N-3-protected nucleosides 7a,b. Reaction of 5a,b with chloromethyl methyl sulfide and/or 2-bromoacetaldehyde diethyl acetal in alkaline medium afforded N-3-alkyl derivatives 8a-c. Reaction of 5a with 1,2-dichloroethane in alkaline conditions afforded bis-thiohydantoinylethane 9a,b. Compounds 5a,b were condensed with formaldehyde and secondary amines to afford 3-aminomethyl-2-thiohydantoins derivatives 10a-d. On the other hand, reaction of unsubstituted 2-thiohydantoins derivatives 11b,c with chloromethyl methyl sulfide afforded the mono- and bis-methylthio derivatives 12a,b and 13a,b, respectively. Reaction of 11b,c with secondary amines and formaldehyde gave 3-aminomethyl-2-thiohydantoins 14a-e. Reaction of 11a-c with bromoacetaldehyde diethyl acetal yielded the S-alkyl derivatives 15a-c which can be hydrolysed with ethanolic hydrochloric acid to afford 5-arylidenehydantoins 16a-c. The compounds do not display any antiviral activity.
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页码:261 / 278
页数:18
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