کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1396703 1501197 2009 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis and cytotoxic profile of glycosyl–triazole linked to 1,2,4-oxadiazole moiety at C-5 through a straight-chain carbon and oxygen atoms
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis and cytotoxic profile of glycosyl–triazole linked to 1,2,4-oxadiazole moiety at C-5 through a straight-chain carbon and oxygen atoms
چکیده انگلیسی

The convergent synthesis of an unusual (but simple) class of compounds 5a–g has been achieved by the copper-catalyzed [3 + 2] cycloaddition reaction of 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl azide 4 with propynyl 3-[3-(aryl)-1,2,4-oxadiazol-5-yl] propionates 3a–g. The formerly known azide 4 has been prepared according to the literature procedure; however, the synthesis of esters 3a–g is being reported for the first time. The infrared as well as 1H NMR spectra of all new products are in agreement with their proposed structures. By carrying out the nOe experiment of one of the final compounds 5a, we have been able to establish that only the 1,4-regioisomers have been formed in the cycloaddition reaction. All final products presented weak cytotoxic activity, but 5e and 5g had somewhat better behaviour showing 22–25% cell growth inhibition against two cell strains: NCI-H292 (lung carcinoma) and HEp-2 (larynx carcinoma).

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 44, Issue 9, September 2009, Pages 3571–3576
نویسندگان
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