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Molecules 2012, 17(7), 8378-8396; doi:10.3390/molecules17078378

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

1
Chemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt
2
Biochemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt
*
Author to whom correspondence should be addressed.
Received: 1 May 2012 / Revised: 10 July 2012 / Accepted: 10 July 2012 / Published: 11 July 2012
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Abstract

5-(1,2,3,4-Tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide (2) was condensed with a variety of ketones to afford carbohydrazide derivatives 36. Acetylation of 35 afforded the acetyl derivatives 79, while periodate oxidation of 36 afforded the formyl derivatives 1013. Acid catalyzed condensation of thiosemicarbazide or o-tolylthiosemicarbazide with the prepared aldehydes 1012 gave thiosemicarbazone derivatives 1419. Cyclization of the latter with acetic anhydride afforded 4,5-dihydro-1,3,4-thiadiazolyl derivatives 2025. On the other hand, condensation of p-tosylhydrazine with the prepared aldehydes 1012 afforded p-tosylhydrazone derivatives 2628. Cyclization of 2628 with acetic anhydride afforded 1,2,3,4-oxathiadiazole derivatives 2931 respectively. Moreover, the obtained results regarding to the effect of some of the prepared compounds on tyrosinase enzyme showed that the majority of these compounds having an inhibitory effect; especially compounds 12, 16, 17, and 28.
Keywords: carbohydrazide; thiosemicarbazone; thiadiazole; oxathiadiazole; tyrosinase carbohydrazide; thiosemicarbazone; thiadiazole; oxathiadiazole; tyrosinase
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

El-Sadek, M.M.; Hassan, S.Y.; Abdelwahab, H.E.; Yacout, G.A. 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. Molecules 2012, 17, 8378-8396.

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