Design, synthesis, and biological activities of some branched carbasugars: construction of a substituted 6-oxabicyclo[3.2.1]nonane skeleton |
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Authors: | Baran Arif Çambul Sinem Nebioglu Mehmet Balci Metin |
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Affiliation: | Department of Chemistry, Sakarya University, 54100 Sakarya, Turkey. baranarif@yahoo.com |
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Abstract: | Transformation of cyclohexa-2,4-diene-1,2-diylbis(methylene) diacetate to various carbasugars is described. Photooxygenation of a cyclohexadiene derivative gave a bicyclicendoperoxide, which was reduced with thiourea to [2-[(acetyloxy)methyl]cyclohexa-2,4-dien-1-yl]methyl acetate. Epoxidation of the remaining double bond followed by epoxide ring-opening and hydrolysis of the acetate groups gave one of the target hexols. The bicyclic endoperoxide was rearranged to a diepoxide with CoTPP. The diepoxide was reacted with sulfamic acid in acetic anhydride, resulting in the formation of a new branched carbasugar as well as in the formation of cyclitols with a 6-oxabicyclo[3.2.1]nonane skeleton. The mechanism of the formation of the products is discussed. The inhibition activity of six cyclitol derivatives was tested against α-glycosidase. |
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