کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1389228 982854 2007 10 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol
چکیده انگلیسی

The synthesis of aza- and thia-spiroheterocycles and the attempted synthesis of spiro sulfonium compounds related to salacinol are described. The binding of the nanomolar inhibitor swainsonine to Drosophila Golgi α-mannosidase II (dGMII) involves a large contribution of interactions between the six-membered ring of the inhibitor and the hydrophobic pocket within the enzyme active site. Salacinol, a naturally occurring sulfonium ion, is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. Spiro aza- and thia-heterocycles and a spiro analogue of salacinol were designed with the expectation that the hydrocarbon portions would make hydrophobic contributions to binding. The former sets of compounds were synthesized successfully but the salacinol analogue proved to be elusive. The stereochemistry of the final compounds was determined by means of 1D-NOESY experiments. The aza- and thia-heterocycles were not effective inhibitors of Golgi α-mannosidase II or human maltase glucoamylase.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 342, Issue 15, 5 November 2007, Pages 2163–2172
نویسندگان
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