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Abstract
The new secondary amine, build of glucose and anthranilic acid—α-glucosiminopyranose anthranilic acid (1)—has been synthesized and characterized by elemental analyses, FT-IR and 1H NMR spectroscopy. Crystal and molecular structure of the hydrate of 1 has been determined by means of X-ray diffraction. 1·H2O crystallizes in monoclinic P21 space group, with a = 15.584(3) A, b = 4.992(1) A, c = 18.928(4) and β = 107.63(3)o. The studies prove that a cyclic secondary amine is formed instead of open chain Schiff base, and only one anomer, α is produced. There are two symmetry-independent molecules of 1·H2O in the asymmetric part of the unit cell, and these independent molecules create complicated hydrogen bonded structures—starting with the homomolecular chains which in turn are joined into three dimensional structure. The differences in the supramolecular structures are correlated with the differences in the bond angles patterns, which result from the different orientations of certain O–H bonds. The antibacterial activities of 1 were also tested but the results were negative.
Highlights
Schiff bases have versatile applications in biochemistry and medicine, for instance they show significant antifungal, antibacterial, and anticancer activities (e.g., [1, 2])
In recent years the molecules designed on anthranilic acid have attracted great interest as they were shown to be able to act through different biological mechanisms that are involved in the development and maintenance of tumoral cells, and possess significant preventive or inhibitory activity [3, 4] in such disorders
Biological activity of sugars is well known since ancient times; for instance they were used in wound treatment—recently promising results have been reported regarding the treatment of infected wounds with granulated sugar, and there are some reports about the efficiency of sugar in the treatment of surgical wounds [5–7]
Summary
Characterization, and Crystal Structure of a-Glucosimino-pyranose Anthranilic Acid. This article is published with open access at Springerlink.com
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