Reaction of o-phenylene diamine with thiosemicarbazide did not give benzotriazine-2-thione 2 as reported, although the product was found to be benzimidazole-2-thione 3. Glycosylation of 3 with acetobromo sugars 4a-4b gave the respective thioglycosides 7a-7d in addition to minor products of the nucleosides 8a and 8b, in the case of the gluco- and galacto-analogs, respectively. The regioselectivity of glycosylation reaction has been investigated.
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
were noticed during its reaction with alkylating agents and glycosyl halides. Alkylating agents gave the Sfunctionalized
derivatives, while the acetylated glycosyl halides afforded the S-glycosylated products together
with their 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 druglikeness
properties.
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