Synthesis and Antimicrobial Screening of Novel Thioglycosides and Acyclonucleoside Analogs Carrying 1,2,3-Triazole and 1,3,4-Oxadiazole Moieties

Nucleosides, Nucleotides & Nucleic Acids
Mohamed R Aouad

Abstract

The solvent-free 1,3-dipolar cycloaddition reaction of dimethylacetylene dicarboxylate (1) with 2-chlorophenyl azide (2) afforded 1,2,3-triazole diester 3 that upon hydrazinolysis, furnished the corresponding bis-acid hydrazide 4. The treatment of compound 4 with carbon disulfide in a refluxing potassium hydroxide solution furnished the desired bis-1,3,4-oxadiazole-2-thione 5 tethered to a 1,2,3-triazole moiety. The respective SOx-glycosides 9-11 were obtained by glycosylation of bis-oxadiazole 5 with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (6), 2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl bromide (7), and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-d-glucopyranosyl chloride (8) in dry acetone in the presence of Et3N, which acted as a base. However, alkylation of 5 with halogeno-alkanol 12 or 13, chloroglycerol 14, bromoethers 20 or 21, and epichlohydrin 22 in the presence of K2CO3 in DMF yielded the corresponding acyclonucleoside analogs 16-18 and 23-25. The isopropylidenes 19 and acetyl derivatives 26-28 of the products were also prepared. The newly synthesized compounds were characterized by (1)H NMR, (13)C NMR, 2D NMR, and mass spectra. The compounds were screened for their antibacterial and antifungal activities. A n...Continue Reading

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Jan 31, 2013·Nucleosides, Nucleotides & Nucleic Acids·Mohamed R AouadEl Sayed H El Ashry

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Citations

Aug 26, 2016·Chemistry : a European Journal·Amélie ChabrierSamir Messaoudi
Mar 21, 2020·Chemical Communications : Chem Comm·Mingxiang ZhuSamir Messaoudi
Feb 7, 2020·Current Pharmaceutical Design·Maria FesatidouAthina Geronikaki
Oct 31, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mohamed R AouadYaseen A Al-Soud
Mar 14, 2019·Mini Reviews in Medicinal Chemistry·Ankit Jain, Poonam Piplani
Sep 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Monika KrawczykKarol Erfurt
Apr 14, 2021·Bioorganic Chemistry·Tukaram B MhamaneSampath Kumar Halmuthur M
Jun 30, 2019·Organic Letters·Mingxiang ZhuSamir Messaoudi
Oct 1, 2021·Chemical Biology & Drug Design·Bhavna SarohaSuresh Kumar

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Methods Mentioned

BETA
glycosidation
acetylation

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