Thiosugar nucleosides. Synthesis and biological activity of 1,3,4-thiadiazole, thiazoline and thiourea derivatives of 5-thio-D-glucose

被引：10

作者：

Al-Masoudi, NA

Al-Soud, YA

Al-Masoudi, WA

机构：

[1] Univ Konstanz, Dept Chem, Constance, Germany

[2] Univ Al Al Bayt, Coll Sci, Dept Chem, Al Mafraq, Jordan

[3] Almergab Univ, Coll Arts & Sci, Dept Chem, Tarhona, Libya

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2004年 / 23卷 / 11期

关键词：

antitumor activity; cumulenes; glycosylimino-1,3,4-thiadiazoles; glycosyl isothiocyanates; glycosylthiourea;

D O I：

10.1081/NCN-200034040

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

New acylated 5-thio-beta-D-glueopyranosylimino-disusbstituted 1,3,4-thiadiazols 8, and 11 were prepared, via spontaneous rearrangements, by cycloaddition of the glycosyl isothiocyanate 2 with the reactive intermediates 1-aza-2-azoniaallene hexachloroantimonates 4 and 6, respectively. Reaction of 2 with aminoacetone or chloroethylamine afforded the acylated 5-thio-beta-D-glucopyranosyl-4-imidazoline-2-thione nucleoside 16 and glucopyranosylamino-2-thiazoline derivative 18, respectively. Deblocking of 8, 11, 17 and 19 furnished the free nucleoside analogues 9, 12, 18 and 20, respectively. Analogously, treatment of 2 with chloroethylamine in the 1:2 ratio afforded the thioureylendisaccharide 21. No in vitro antiviral activity against HIV-1, HIV-2, human cytomegallovirus (HMCV), has been found for the new synthesized compounds.

引用

页码：1739 / 1749

页数：11

共 42 条

[1] Synthesis and reactions of 1,5- and 1,3-dialkyl-(D-manno-pentitol-1-yl)-1H-1,2,4-triazole nucleosides derived from 1-(chloroalkyl)-1-aza-2-azoniaallene salts [J].