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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[2]. Yu-Fei Wang, Li-Ping Wang, Shao-Peng Wang, Yu-Ling Li, Xiao-Li Zhou
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References

[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.
http://dx.doi.org/10.1016/j.bmc.2005.10.064
PMid:16310359

[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.
http://dx.doi.org/10.1016/j.ejmech.2006.12.038
PMid:17418454

[3]. Heindel, N. D.; Reid, J. R. J. Heterocycl. Chem. 1980, 17, 1087-1088.
http://dx.doi.org/10.1002/jhet.5570170547

[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.
http://dx.doi.org/10.1016/0223-5234(94)90100-7

[5]. Mathew, V.; Keshavayya, J.; Vaidya, V. P. Eur. J. Med. Chem. 2006, 41, 1048-1058.
http://dx.doi.org/10.1016/j.ejmech.2006.03.018
PMid:16822595

[6]. Mathew, V.; Giles, D.; Keshavayya, J.; Vaidya, V. P. Arch. Pharm. 2009, 342, 210-222.
http://dx.doi.org/10.1002/ardp.200800073
PMid:19340834

[7]. Karthikeyan, M. S.; Holla, B. S.; Kulkuraya, B.; Kumari, N. S. Monatsh. Chem. 2007, 138, 1309-1316.
http://dx.doi.org/10.1007/s00706-007-0718-y

[8]. Sharma, R.; Sainy, J.; Chaturvedi, S. C. Acta. Pharm. 2008, 58, 317-326.
http://dx.doi.org/10.2478/v10007-008-0011-6
PMid:19103568

[9]. Prasad, D. J.; Ashok, M.; Karegoudar, P.; Poojary, B.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2009, 44, 551-557.
http://dx.doi.org/10.1016/j.ejmech.2008.03.025
PMid:18508161

[10]. Karegoudar, P.; Prasad, D. J.; Ashok, M.; Mahalinga, M.; Poojary, B.; Holla, B. S.; Eur. J. Med. Chem. 2008, 43, 808-815
http://dx.doi.org/10.1016/j.ejmech.2007.06.026
PMid:17804121

[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.
http://dx.doi.org/10.1016/j.ejmech.2006.09.001
PMid:17052805

[13]. Amir, M.; Kumar, H.; Javed, S. A. Bioorg. Med. Chem. Lett. 2007, 17, 4504-4508.
http://dx.doi.org/10.1016/j.bmcl.2007.06.003
PMid:17576062

[14]. Golovlyova, S. M.; Moskvichev, Yu. A.; Alov, E. M.; Kobylinsky, D. B.; Ermolaeva, V. V. Chem. Heterocycl. Compd. 2001, 37, 1102-1106.
http://dx.doi.org/10.1023/A:1013275515682

[15]. Labanauskas, L.; Udrenaite, E.; Gaidelis, P.; Brukstus, A. Farmaco 2004, 59, 255-259.
http://dx.doi.org/10.1016/j.farmac.2003.11.002
PMid:15081342

[16]. Tozkoparan, B.; Gokhan, N.; Aktay, G.; Yesilada, E.; Ertan, M. Eur. J. Med. Chem. 2000, 35, 743-750.
http://dx.doi.org/10.1016/S0223-5234(00)00157-4

[17]. Ozturk, S.; Akkurt, M.; Causiz, A.; Koparir, M.; Sekerci, M.; Heinemann, F. W. Acta Cryst. E 2004, 60, o425-o427.
http://dx.doi.org/10.1107/S1600536804003721

[18]. Koparir, M.; Cetin, A.; Causiz, A. Molecules 2005, 10, 475-480.
http://dx.doi.org/10.3390/10020475
PMid:18007318

[19]. Okeke, M. I.; Iroegbu, C. U.; Eze, E. N.; Okoli, A. S.; Esimone, C. O. J. Ethnopharmacol. 2001, 78, 119-127.
http://dx.doi.org/10.1016/S0378-8741(01)00307-5

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. 25 Jan. 2020
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)

DOI Link: https://doi.org/10.5155/eurjchem.3.4.485-492.655

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