European Journal of Chemistry 2012, 3(4), 485-492 | doi: https://doi.org/10.5155/eurjchem.3.4.485-492.655 | Get rights and content

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Regiospecific synthesis of some novel N-nucleosides of 4-amino-5-substituted-1,2,4-triazole-3-thiones and their in-vitro antimicrobial activity


Humaira Nadeem (1) , Zaman Ashraf (2,*)

(1) Riphah Institute of Pharmaceutical Sciences, Riphah International University, Islamabad, 44000, Pakistan
(2) Department of Chemistry, Allama Iqbal Open University, Islamabad, 44000, Pakistan
(*) Corresponding Author

Received: 20 Jun 2012 | Revised: 26 Sep 2012 | Accepted: 05 Nov 2012 | Published: 31 Dec 2012 | Issue Date: December 2012

Abstract


4-Amino-5-substituted-1,2,4-triazole-3-thiones were prepared by following two different reaction routes and comparing the effectiveness of using different reaction conditions. The coupling of aminotriazoles with acetylated α-bromo-D-glucose furnished protected N-nucleosides regiospecifically. The reagents used gave only one regioisomer N-glycosides not the other S-nucleosides. The protected nucleosides upon deacetylation using methanolic ammonia afforded deprotected products. The chemical structures of synthesized compounds were confirmed by FT-IR, 1H NMR, 13C NMR, mass spectroscopic and elemental analysis data. All of the synthesized compounds were tested against ten different gram positive and gram negative bacterial strains which exhibited moderate to good antibacterial activity. The deprotected nucleosides portrayed high antibacterial activity than 4-amino-5-substituted-1,2,4-triazole-3-thiones and protected nucleosides against selected bacteria.

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Keywords


Spectroscopy; N-nucleosides; Regiospecificity; Antimicrobial activity; 1,2,4-Triazole-3-thiones; 5-Aryl/hetero aryl substitution

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DOI: 10.5155/eurjchem.3.4.485-492.655

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Funding information


Riphah Institute of Pharmaceutical Sciences, Riphah International University, Islamabad, Pakistan

Citations

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[1]. Yufei Wang, Liping Wang, Xiaoli Zhou, Yuling Li, Jingjing Li
Three Cd(II) complexes based on pyridine containing mercapto-triazole and aromatic multi-carboxylates: Syntheses, structures and luminescent properties
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DOI: 10.1016/j.molstruc.2018.07.025
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[2]. Yu-Fei Wang, Li-Ping Wang, Shao-Peng Wang, Yu-Ling Li, Xiao-Li Zhou
Four Zn/Pb Complexes based on Pyridine containing Mercapto-triazole Ligand: Syntheses, Structures, and Luminescent Properties
Zeitschrift für anorganische und allgemeine Chemie  644(19), 1164, 2018
DOI: 10.1002/zaac.201800199
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How to cite


Nadeem, H.; Ashraf, Z. Eur. J. Chem. 2012, 3(4), 485-492. doi:10.5155/eurjchem.3.4.485-492.655
Nadeem, H.; Ashraf, Z. Regiospecific synthesis of some novel N-nucleosides of 4-amino-5-substituted-1,2,4-triazole-3-thiones and their in-vitro antimicrobial activity. Eur. J. Chem. 2012, 3(4), 485-492. doi:10.5155/eurjchem.3.4.485-492.655
Nadeem, H., & Ashraf, Z. (2012). Regiospecific synthesis of some novel N-nucleosides of 4-amino-5-substituted-1,2,4-triazole-3-thiones and their in-vitro antimicrobial activity. European Journal of Chemistry, 3(4), 485-492. doi:10.5155/eurjchem.3.4.485-492.655
Nadeem, Humaira, & Zaman Ashraf. "Regiospecific synthesis of some novel N-nucleosides of 4-amino-5-substituted-1,2,4-triazole-3-thiones and their in-vitro antimicrobial activity." European Journal of Chemistry [Online], 3.4 (2012): 485-492. Web. 29 Nov. 2021
Nadeem, Humaira, AND Ashraf, Zaman. "Regiospecific synthesis of some novel N-nucleosides of 4-amino-5-substituted-1,2,4-triazole-3-thiones and their in-vitro antimicrobial activity" European Journal of Chemistry [Online], Volume 3 Number 4 (31 December 2012)

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