| Design and synthesis of novel 1,3,4-thiadiazole thioglycosides as promising potent structures in medicinal chemistry |
| Paper ID : 1053-ISCHU |
| Authors |
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T.Salama Hagar *1, A. Abu-Zaied Mamdouh2, M.S.Hebishy Ali3, H.Elgemeie Galal4 1Chemistry Department, Faculty of Science, Helwan University, Cairo, Egypt 2Green Chemistry Department, National Research Centre, Dokki, Giza 3Chemistry Department,Faculty Of Science,HelwanUniversity,Cairo,Egypt 4Chemistry Department, Faculty of Science, Helwan University, Egypt |
| Abstract |
| Heterocyclic compounds hold significant importance within the field of medicinal chemistry. Among these compounds, 1,3,4-thiadiazoles represent a prominent class of heterocyclic structures with diverse applications in organic synthesis, biological contexts, and the pharmaceutical industry. They have played a pivotal role in the development of various pharmaceuticals, including anti-inflammatory agents, anti-hypertensives, anti-HIV medications, local anesthetics, antidepressants, and anticonvulsants. In addition, the sugar moieties are recognized for their ability to influence the pharmacokinetic properties of these heterocyclic compounds, impacting factors like absorption, metabolism, distribution, and acting as carriers while enhancing selectivity for cancerous cell lines. Our main goal was the synthesis of 1,3,4-thiadiazole thioglycosides. We achieved this by initially reacting alkyl or aryl isothiocyanate with hydrazine hydrate to obtain the corresponding thiosemicarbazide derivatives. Subsequent treatment of these derivatives with carbon disulfide yielded potassium 1,3,4-thiadiazole thiolates. These compounds were then subjected to reactions with protected α-D-gluco- and galacto-pyranosyl bromides, resulting in the formation of either protected 1,3,4-thiadiazole S-glycosides or the isomeric N-glycosides, representing two distinct modes of glycosylation. The deprotection of the initially protected thioglycosides through treatment with NH3-MeOH led to the production of the final products, which could either be the 1,3,4-thiadiazole S-glycosides or the isomeric N-glycosides. |
| Keywords |
| 1,3,4-thiadiazole, 1,3,4-thiadiazole thioglycosides |
| Status: Abstract Accepted (Poster Presentation) |