کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1389035 982838 2008 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moiety
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis and biological activity of novel thiazolidin-4-ones with a carbohydrate moiety
چکیده انگلیسی

Some novel 2-aryl-3-[5-deoxy-1,2-O-isopropylidene-α-d-xylofuranose-5-C-yl] thiazolidin-4-ones were synthesized by the three-component condensation of an amino sugar 1, an aromatic aldehyde 2, and mercaptoacetic acid 3 in the presence of DCC and DMAP at room temperature. Two diastereoisomers 4 and 5 were afforded as the main products in totally isolated yields of 25.4–70%. The reaction was carried out with almost no observed stereoselectivity except in the case of 2c, which showed a moderate stereoselectivity. The structures of the new compounds were determined by NMR spectroscopy and mass spectrometry (MS), and the configuration of the newly generated chiral carbon (C-2) in the thiazolidin-4-one ring was tentatively assigned based on the X-ray crystallographic structure of 5d and the comparison of their corresponding NMR signals. The antitumor (human cervical cancer cells) activity and the inhibition against the glycosidases (α-glucosidase, β-glucosidase, α-amylase) have been evaluated for the new compounds, some of which exhibited antitumor activity.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Carbohydrate Research - Volume 343, Issue 18, 8 December 2008, Pages 3015–3020
نویسندگان
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