کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1390539 983102 2011 8 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors
چکیده انگلیسی
An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from d-(−)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against β-galactosidase (IC50 = 3 μM). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 346, Issue 2, 1 February 2011, Pages 183-190
نویسندگان
, , , ,