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Synthesis and Antioxidant Activity of Novel 5-amino-2-alkyl/glycosylthio-1,3,4- thiadiazoles: Regioselective Alkylation and Glycosylation of the 5-amino-1,3,4- thiadiazole-2-thiol Scaffold

Author(s):

El Sayed H. El Ashry*, El Sayed Ramadan, Mohammed R. Amer, Yeldez El Kilany, Mohamed E. I. Badawy and Entsar I. Rabea   Pages 1 - 9 ( 9 )

Abstract:


Background and Objective: 5-Amino-2-alkyl/glycosylthio-1,3,4-thiadiazoles have been synthesized by the reaction of 5-amino-1,3,4-thiadiazole-2-thiol with a variety of alkylating agents or glycosyl halides in the presence of anhydrous potassium carbonate in dry acetone.

Methods: The structures of the newly synthesized compounds have been established based on their spectral data (FT-IR, 1H- and 13C-NMR) and mass spectrometry. They were tested for their antioxidant behaviour by the use of 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. The in silico pharmacokinetics ADME properties of the potent antioxidant compounds were investigated by using Accelrys Discovery Studio (DS) 2.5 software.

Results and Conclusion: Regioselective alkylation and glycosylation of 5-amino-1,3,4-thiadiazole-2-thiol was noticed during its reaction with alkylating agents and glycosyl halides. Alkylating agents gave the S-functionalized derivatives, while the acetylated glycosyl halides afforded the S-glycosylated products together with its respective N-acetyl derivatives. The benzoylated glycosyl halide behaved in a different manner and gave N-glycoside analogue of 1,3,4-thiadiazole-2(3H)-thione, in addition to the expected sulfanyl S-glycoside. Most of the synthesized compounds showed noticeable antioxidant activity with respect to ceftriaxone as a standard drug. Some of the most active compounds showed acceptable predicted pharmacokinetics and drug-likeness properties.

Keywords:

thiadiazole-2-thiol, alkylation, antioxidant activity, glycosylation, pharmacokinetics ADME analysis

Affiliation:

Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21524, Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21524, International Center for Chemical and Biological Science, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi 75270, Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21524, Department of Pesticide Chemistry and Technology, Faculty of Agriculture, El-Shatby, Alexandria University, Alexandria 21545, Department of Plant Protection, Faculty of Agriculture, Damanhour University, Damanhour 22516



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