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

Mohamed M. El-Sadek¹  Seham Y. Hassan¹  Huda E. Abdelwahab¹ 

[1] ¹Chemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt ²Biochemistry Department, Faculty of Science, Alexandria University, Alexandria 21231, Egypt

关键词: carbohydrazide;    thiosemicarbazone;    thiadiazole;    oxathiadiazole;    tyrosinase;   

DOI  :  10.3390/molecules17078378

来源: mdpi

【 摘 要 】

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 afforded p-tosylhydrazone derivatives 26–28. Cyclization of 26–28 with acetic anhydride afforded 1,2,3,4-oxathiadiazole derivatives 29–31 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.

【 授权许可】

CC BY   
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