Regioselective synthesis, characterization and antimicrobial evaluation of S-glycosides and S,N-diglycosides of 1,2-Dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione.

Autor: El Ashry el SH; HEJ Research Institute for Chemistry, International Center for Chemical and Biological Sciences, Karachi University, Karachi, Pakistan. eelashry60@hotmail.com, El Tamany el SH, El Fattah Mel D, Boraei AT, Abd El-Nabi HM
Jazyk: angličtina
Zdroj: European journal of medicinal chemistry [Eur J Med Chem] 2013 Aug; Vol. 66, pp. 106-13. Date of Electronic Publication: 2013 May 20.
DOI: 10.1016/j.ejmech.2013.04.047
Abstrakt: Glycosylation of 1,2-Dihydro-5-(1H-indol-2-yl)-1,2,4-triazole-3-thione with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide, 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride was investigated in the presence of Et₃N and K₂CO₃ as acid scavengers. A regioselective S-glycosides were obtained by using Et₃N whereas, using K₂CO₃ gave a mixtures of two hybrids having two glycosidic bonds. The two products of each mixture were separated and characterized as S,N(1)- and S,N(2)-bis(glycosylated) derivatives. The structures of the newly synthesized compounds were elucidated by (1)H NMR, (13)C NMR, 2D NMR and mass spectra. The compounds were screened for their antibacterial and antifungal activities. Some compounds exhibited strong inhibition activity compared with the reference drugs (chloramphenicol and baneocin).
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Databáze: MEDLINE
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