synthesis of new 1,3,4-thiadiazole and 1,2,3,4-oxathiadiazole derivatives from carbohydrate precursors and study of their effect on tyrosinase enzyme合成的新1 3 4-thiadiazole和1,2,3,4-oxathiadiazole衍生品从碳水化合物前体和研究对酪氨酸酶酶的影响.pdfVIP

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synthesis of new 1,3,4-thiadiazole and 1,2,3,4-oxathiadiazole derivatives from carbohydrate precursors and study of their effect on tyrosinase enzyme合成的新1 3 4-thiadiazole和1,2,3,4-oxathiadiazole衍生品从碳水化合物前体和研究对酪氨酸酶酶的影响.pdf

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synthesis of new 1,3,4-thiadiazole and 1,2,3,4-oxathiadiazole derivatives from carbohydrate precursors and study of their effect on tyrosinase enzyme合成的新1 3 4-thiadiazole和1,2,3,4-oxathiadiazole衍生品从碳水化合物前体和研究对酪氨酸酶酶的影响

Molecules 2012, 17, 8378-8396; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of New 1,3,4-Thiadiazole and 1,2,3,4-Oxathiadiazole Derivatives from Carbohydrate Precursors and Study of Their Effect on Tyrosinase Enzyme Mohamed M. El-Sadek 1,*, Seham Y. Hassan 1, Huda E. Abdelwahab 1 and Galila A. Yacout 2 1 Chemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt; E-Mails: sehamyassen@ (S.Y.H.); huda_eid@ (H.E.A.) 2 Biochemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt; E-Mail: galila_69@ * Author to whom correspondence should be addressed; E-Mail: elsadek_mm@; Tel.: +20-01-006-544-617; Fax: +20-3-5932-488. Received: 1 May 2012; in revised form: 10 July 2012 / Accepted: 10 July 2012 / Published: 11 July 2012 Abstract: 5-(1,2,3,4-Tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide (2) was condensed with a variety of ketones to afford carbohydrazide derivatives 3–6. Acetylation of 3–5 afforded the acetyl derivatives 7–9, while periodate oxidation of 3–6 afforded the formyl derivatives 10–13. Acid catalyzed condensation of thiosemicarbazide or o-tolylthiosemicarbazide with the prepared aldehydes 10–12 gave thiosemicarbazone derivatives 14–19. Cyclization of the latter with acetic anhydride afforded 4,5-dihydro- 1,3,4-thiadiazolyl derivatives 20–25. On the other hand, condensation of p -tosylhydrazine with the prepared aldehydes 10–12 afforde