European Journal of Chemistry

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

Main Article Content

Humaira Nadeem
Zaman Ashraf


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.


icon graph This Abstract was viewed 1491 times | icon graph Article PDF downloaded 734 times

How to Cite
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, 485-492.

Article Details

Crossref - Scopus - Google - European PMC

[1]. Silvia, S.; Chiara, B.; Olga, B.; Francesco, B.; Angelo, R.; Walter, F.; Barbara, R.; Annalisa, C.; Giuseppe, F. Bioorg. Med. Chem. 2006, 14, 1698-1705.

[2]. Kucukguzel, S. G.; Kucukguzel, I.; Tatar, E.; Rollas, S.; Sahin, F.; Gulluce, M.; DeClercq, E.; Kabasakal, L. Eur. J. Med. Chem. 2007, 42, 893-901.

[3]. Heindel, N. D.; Reid, J. R. J. Heterocycl. Chem. 1980, 17, 1087-1088.

[4]. Holla, B. S.; Kalluraya, B.; Sridhar, K. R.; Drake, E.; Thomas, L. M.; Bhandary, K. K.; Levine, M. Eur. J. Med. Chem. 1994, 29, 301-308.

[5]. Mathew, V.; Keshavayya, J.; Vaidya, V. P. Eur. J. Med. Chem. 2006, 41, 1048-1058.

[6]. Mathew, V.; Giles, D.; Keshavayya, J.; Vaidya, V. P. Arch. Pharm. 2009, 342, 210-222.

[7]. Karthikeyan, M. S.; Holla, B. S.; Kulkuraya, B.; Kumari, N. S. Monatsh. Chem. 2007, 138, 1309-1316.

[8]. Sharma, R.; Sainy, J.; Chaturvedi, S. C. Acta. Pharm. 2008, 58, 317-326.

[9]. Prasad, D. J.; Ashok, M.; Karegoudar, P.; Poojary, B.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2009, 44, 551-557.

[10]. Karegoudar, P.; Prasad, D. J.; Ashok, M.; Mahalinga, M.; Poojary, B.; Holla, B. S.; Eur. J. Med. Chem. 2008, 43, 808-815

[11]. Udupi, R. H.; Rajeeva, B.; Srinivasulu, N.; Pasha, T. Y.; Setty, S. R.; Bhat, A. R. Indian J. Heterocycl. Chem. 2004, 13, 233-236.

[12]. Metwally, K. A.; Yaseen, S. H.; Lashine, S. M.; El-Fayomi, H. M.; El-Sadek, M. E. Eur. J. Med. Chem. 2007, 42, 152-160.

[13]. Amir, M.; Kumar, H.; Javed, S. A. Bioorg. Med. Chem. Lett. 2007, 17, 4504-4508.

[14]. Golovlyova, S. M.; Moskvichev, Yu. A.; Alov, E. M.; Kobylinsky, D. B.; Ermolaeva, V. V. Chem. Heterocycl. Compd. 2001, 37, 1102-1106.

[15]. Labanauskas, L.; Udrenaite, E.; Gaidelis, P.; Brukstus, A. Farmaco 2004, 59, 255-259.

[16]. Tozkoparan, B.; Gokhan, N.; Aktay, G.; Yesilada, E.; Ertan, M. Eur. J. Med. Chem. 2000, 35, 743-750.

[17]. Ozturk, S.; Akkurt, M.; Causiz, A.; Koparir, M.; Sekerci, M.; Heinemann, F. W. Acta Cryst. E 2004, 60, o425-o427.

[18]. Koparir, M.; Cetin, A.; Causiz, A. Molecules 2005, 10, 475-480.

[19]. Okeke, M. I.; Iroegbu, C. U.; Eze, E. N.; Okoli, A. S.; Esimone, C. O. J. Ethnopharmacol. 2001, 78, 119-127.

Supporting Agencies

Riphah Institute of Pharmaceutical Sciences, Riphah International University, Islamabad, Pakistan
Most read articles by the same author(s)

Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).