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SM ISO690:2012 BILAN, Dmitri, SUCMAN, Natalia, POGREBNOI, Vsevolod, KRAVTSOV, Victor, MAKAEV, Fliur. The structure of N-glycosylated spiro[oxindol-thiadiazole]. In: Materials Science and Condensed Matter Physics, Ed. 9, 25-28 septembrie 2018, Chișinău. Chișinău, Republica Moldova: Institutul de Fizică Aplicată, 2018, Ediția 9, p. 167. |
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Materials Science and Condensed Matter Physics Ediția 9, 2018 |
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Conferința "International Conference on Materials Science and Condensed Matter Physics" 9, Chișinău, Moldova, 25-28 septembrie 2018 | ||||||
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CZU: 547.7/.8:615.011+539 | ||||||
Pag. 167-167 | ||||||
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Spiro cyclopropyl oxindoles have become the focus of intense investigation during the last decades due to their delicate framework. The skeleton rigidity of this framework ensures a strictly defined spatial sustainability of substituents, and the possibility of specific interactions with biological targets. The promising biological activities of natural and unnatural spirooxindole derivatives have promoted the special focusing of organic chemists on their synthesis [1-3]. In the last time, especial attention is devoted to such structures due to the fact that they are the inhibitors of HIV-1. We have recently designed and synthesized several N-alkylated spiro[oxindol-thiadiazoles] with a good activity against viruses containing a single-stranded positive-sense RNA genome (ssRNA+) [4]. On the other side, glycosylation of heterocycles that are rich in biological activity is a field of increasing interest as shown, for example, by the synthesis of various guanidinoglycosides displaying improved biological properties (anti-influenza and anti-HIV activities) with respect to the nonglycosylated guanidino derivatives [5]. In our attempts to search for novel non-nucleoside reverstranscriptase inhibitors, we planned to synthesize N-glycosylated derivative of known spiro[oxindol-thiadiazole]. Target compound was obtained through six-step synthesis and characterized by elemental analysis, IR-, 1H NMR-, 13C NMR spectroscopy and by X-ray analysis. Compound crystallizes in the form of monohydrate in monoclinic non-centrosymmetric P21 space group, a = 9.1988(5), b = 9.2847(4), c = 20.2128(12) Å, ß = 97.001(5)°, V = 1713.47Å3, Z=2. Two O1w-H···O hydrogen bonds 2.869(8) and 3.048(10) Å and one N4-H···O1w =2.865(8) Å unite molecules in ribbons parallel to b crystallographic axis. The N3=C double bond equals 1.277(6) Å. The dihedral angle between oxindol and thiadiazole fragments equals 84.7°. The investigation of the biological activity of synthesized compounds is in progress. Our further work will be directed towards obtaining of new derivatives or cocrystals active against HIV-1 reverse transcriptase and integrase with attached esterase sensitive motif. |
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