Thio-glycomimetics with enhanced lipophilicity and their biological activity

被引：4
|
作者：
Witczak, Zbigniew J. [1 ]
Mauger, Anastasia [1 ]
Bielski, Roman [1 ]
Mencer, Donald E. [2 ]
机构：
[1] Wilkes Univ, Dept Pharmaceut Sci, 84W South St, Wilkes Barre, PA 18766 USA
[2] Wilkes Univ, Dept Chem & Biochem, 84W South St, Wilkes Barre, PA 18766 USA
来源：
ARKIVOC | 2021年
关键词：
Adamantanes; levoglucosenone; 1,4-S-thiodisaccharides; 2-thiazoline; 1,3,4-thiadiazole; STEREOSELECTIVE-SYNTHESIS; THIOSUGARS; SUGARS;
D O I：
10.24820/ark.5550190.p011.394
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The thio-linked glycomimetics were prepared via a base-catalyzed, highly stereo-selective Michael condensation of levoglucosenone with various sugar, heterocyclic and adamantane thiols in order to generate a library of analogs with comparative level of lipophilicity for further biological screening as antibacterial and anticancer agents. The comparative analysis of earlier synthesized library of previously synthesized glycomimetics with the new analogs exhibiting more lipophilic character is also presented. H-1 NMR, C-13 NMR, and single-crystal x-ray diffraction of the unexpected addition and cyclization product unequivocally confirm the structural assignments. Mechanistic insights related to the synthesis of new products are also proposed and discussed.
引用
收藏
页码：268 / 279
页数：12
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