SciELO - Scientific Electronic Library Online

 
vol.65Comparison of tetrahydroisoquinoline (TIQ) thiazole and oxazoline ligands for asymmetric Henry reactionsRapid synthesis of 2-substituted-2,3-dihydro-4(1H)-quinazolinones using boric acid or sodium dihydrogen phosphate under solvent-free conditions índice de autoresíndice de materiabúsqueda de artículos
Home Pagelista alfabética de revistas  

Servicios Personalizados

Articulo

Indicadores

Links relacionados

  • En proceso de indezaciónCitado por Google
  • En proceso de indezaciónSimilares en Google

Compartir


South African Journal of Chemistry

versión On-line ISSN 1996-840X
versión impresa ISSN 0379-4350

S.Afr.j.chem. (Online) vol.65  Durban  2012

 

RESEARCH ARTICLE

 

Synthesis and antibacterial activity of some 5,5'-(1,4-phenylene)-bis-1,3,4-oxadiazole and bis-1,2,4-triazole derivatives as precursors of new S-nucleosides

 

 

Yazid DatoussaidI, *; Adil A. OthmanI; Gilbert KirschII

ILaboratory of Biomolecular and Organic Synthesis, Chemistry Department, Faculty of Science, University of Sciences and Technology-Mohamed Boudiaf-Oran-USTO, P.O.B. 1505 El-M'naouer, 31000, Oran, Algeria
IILaboratoire d'Ingénierie Moleculaire et Biochimie Pharmacologique, Université Verlaine, Metz 57070, France

 

 


ABSTRACT

Five compounds, namely 5,5'-benzene-1,4-diylbis(1,3,4-oxadiazole-2-thiol)6 and 5,5'-benzene-1,4-diylbis(1H-1,2,4-triazole-3-thiol) 7a and its derivatives 7b-d were synthesized. Two related S-nucleosides 9 and 10 have been prepared from 6 and 7a Some of these synthesized compounds were tested in vitro by spotting on Mueller Hinton Agar medium against some Gram-positive bacteria, Staphylococcus aureus and Enterococcus faecalis and three Gram-negative bacteria Escherichia coli, Pseudomonasaeruginosa, Pseudomonas fluorescens and compared with the known antibiotics cephalosporin (cefotaxim) and gentamycin. Compound 6: showed significant inhibitory activity against Gram-positive E. faecalis and Gram-negative E. coli bacteria while the others have shown variable inhibition activity.

Keywords: Terephthalic acid, 1,3,4-oxadiazole, 1H-1,2,4-triazole, S-nucleosides, antimicrobial activity


 

 

Full text available only in PDF format.

 

Acknowledgements

Thanks are due to Professor M. Kihel and Mr. A. Mami of the Laboratory of Applied Microbiology, Faculty of Science, University of Oran, Essenia, Oran, for discussion and technical assistance. We also thank Mrs Veronique Poddig of 'Laboratoire d'ingénierie moléculaire et biologie pharmacologique de l' Université de Metz, France, for recording the NMR spectra and Dr. Serge Schneider of Université de Luxembourg, Luxembourg, for recording the mass spectra.

 

References

1 H. Hanaki, Y.Yamaguchi and S. Nomura, Int. J. Antimicrob. Agents, 2004, 23, 1-5.         [ Links ]

2 L.E. Nunez, C. Mendez, A.F. Brana and G. Blanco, Chem. Biol. 2003, 10, 301-311.         [ Links ]

3 E. De Clercq, J. Clin. Virol. 2004, 30, 115-133.         [ Links ]

4 A. Matsuda and T. Sasaki, Cancer Sci. 2004, 95, 105-111.         [ Links ]

5 D.M. Huryn and M. Okabe, Chem. Rev. 1992, 92, 1745-1768.         [ Links ]

6 T. Pathak, Chem. Rev. 2002, 102, 1623-1667.         [ Links ]

7 C. Len and G. Mackenzie, Tetrahedron, 2006, 62, 9085-9107.         [ Links ]

8 E.S.H. El Ashry and Y. El Kilany, Adv. Heterocycl. Chem, 1997, 67, 391-438.         [ Links ]

9 E.S.H. El Ashry and Y. El Kilany, Adv. Heterocycl. Chem, 1998, 69, 129-215.         [ Links ]

10 A.B.A. El-Gazzar, H.N. Hafez and H.-A.S. Abbas, Eur. J. Med. Chem. 2009, 44, 4249-4258.         [ Links ]

11 G. Casiraghi, M. Cornia, G. Rassu, C. DelSante and P. Spanu, Tetrahedron, 1992, 48, 5619-5628.         [ Links ]

12 A.Z. Nasr, Nucleosides, Nucleotides and Nucleic Acids, 2003, 22, 349-357.         [ Links ]

13 C. Andersen, P.K. Sharma, M.S. Christensen, N.S. Pedersen and P. Nielsen, Nucleic Acids Symposium Series, 2008, 52, 275-276.         [ Links ]

14 A. Talukdar, B. Illarionov, A. Bacher, M. Fischer and M. Cushman, J. Org. Chem. 2007, 72, 7167-7175.         [ Links ]

15 H.N. Hafez, H.A.R. Hussein and A-R.B.A. El-Gazzar, Eur. J. Med. Chem., 2010, 45, 4026-4034.         [ Links ]

16 C.L. Nance, E.B. Siwak and W.T. Shearer, J. Allergy Clin. Immunol, 2009, 123, 459-465.         [ Links ]

17 P. Zhan, X.Y. Liu, Z.J. Fang, C. Pannecouque and E. De Clercq, Chem. Biodivers, 2010, 7, 1717-1727.         [ Links ]

18 H.N. Hafez, A.B.A. El-Gazzar and G.A.M. Nawwar, Eur. J. Med. Chem. 2010, 45, 1485-1493.         [ Links ]

19 Z.K. Rio, J. Long, C. Li, S.S. Zhang, M.L. Ou, Y.T. Zheng and Y.P. He, Monatsh. Chem, 2008, 139, 967-974.         [ Links ]

20 S. Saxena and A.K. Pandey, Appl. Microbiol. Biotechnol. 2001, 55, 395-403.         [ Links ]

21 L. Cui, G. Dai, L. Xu, S. Wang, L. Song, R. Zhao, H. Xiao, J. Zhou and X. Wang, Toxicology, 2004, 201, 59-66.         [ Links ]

22 M. Akhtar, A. Husain, B. Azad and M. Ajmal, Eur. J. Med. Chem, 2009, 44, 2372-2378        [ Links ]

23 E-D. Chenot, D. Bernardi, A. Comel and G Kirsch, Synth. Commun. 2007, 37, 483-490.         [ Links ]

24 F. Barsoum and A. Girgis, Eur. J. Med. Chem., 2009, 44, 2172-2177.         [ Links ]

25 S. Shahzadi, K. Shahid, S. Ali, M. Mazhar and K.M. Khan, J. Iranian Chem. Soc, 2005, 2, 277-288.         [ Links ]

26 A. Mavrova, D. Wesselinova, Y. Tsenov and P. Denkova. Eur. J. Med. Chem. 2009, 44, 63-69.         [ Links ]

27 A. Aboraia, H. Abdel Rahman, N. Mahfouz and M.A. El-Gendy, Bioorg. Med. Chem., 2006, 14, 1236-1246.         [ Links ]

28 Z. Khiati, A.A. Othman and B. Guessas, S.Afr.J.Chem., 2007, 60, 20-24.         [ Links ]

29 R. Udupi, S. Sudheendra, B. Bheemachari, N. Srinvasalu, R. Varnekar and P. Purushottamacher, Bull. Korean Chem. Soc., 2007, 28, 2235-2240.         [ Links ]

30 M. Serwar, T. Akhtar, S. Hameed and K. Khan, Arkivoc, 2009, 3, 210-221.         [ Links ]

31 H. Tashoush, S. Bataineh and M. Al-Talib, Asian J. Chem., 2001, 13, 111-118.         [ Links ]

32 P.C. Joshi, Asian J. Chem., 1996, 8, 412-418.         [ Links ]

33 C. Ainsworth, J. Am. Chem. Soc., 1956, 78, 4475^478.         [ Links ]

34 V. Zaharia, L. Vlase and N. Palibroda, Farmacia, 2001, 49, 54-61.         [ Links ]

35 M.G. Assy, M.M. Hassanien and G.A. Ahmed, Phosphorus, Sulfur, Silicon Relat. Elem., 1995, 102, 65-69.         [ Links ]

36 K. Dubey, S. Kumar and N.K. Naresh, Indian J. Chem., Sec. B: Organic Chemistry Including Medicinal Chemistry, 1994, 33, 1159-1164.         [ Links ]

37 P.P. Gupta, M.L. Sachdeva and H.K. Pujari, Indian J. Chem., Sec. B: Organic Chemistry IncludingMedicinal Chemistry, 1977, 15, 746-747.         [ Links ]

38 J.F. Willems and A. Vandenberghe, Bull. Soc. Chim. Belges, 1966, 75, 358-365.         [ Links ]

39 E. Pretsh, P. Buhlmann and C. Affolter in Structure Determination of Organic Compounds - Tables of spectral Data, Springer-Verlag, Berlin Heidelberg, 2000, 158.         [ Links ]

40 A. Zhang, L. Zhang and X. Lei, Magn.Reson. Chem., 2006, 44,813-816.         [ Links ]

41 VS. Palekar, A.M. Damle and S.R. Shukla, Eur. J. Med. Chem., 2009, 44, 5112-5116.         [ Links ]

42 A.K. Dubey and N.K. Sangwan, Indian J. Heterocycl. Chem., 1994, 3, 277-280.         [ Links ]

43 J. Mohan, G.S.R. Anjaneyulu, S. Sudhir and D.R. Arora, J. Indian Chem. Soc., 1989, 66, 330-331.         [ Links ]

44 M.M.S. Dallal, M.P. Doyle, M. Rezadehbashi, H. Dabiri, M. Sanaei, S. Modarresi, R. Bakhtiari, K. Sharifiy, M. Taremi, M.R. Zali and M.K. Sharifi-Yazdi, Food Control, 2010, 21, 388-392.         [ Links ]

45 Clinical and Laboratory Standards Institute, Performance Standards for Antimicrobial Susceptibily Testing; Sixteenth International Supplement, 2006, 26, 11-35.         [ Links ]

46 National Committee for Clinical and Laboratory Standards Villanova, PA, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 4/e, 1997.         [ Links ]

47 M.A. Azam, B. Suresh, S.S. Kalsi and A.S. Antony, S. Afr. J. Chem.; 2010, 63, 114-122.         [ Links ]

48 S. Benhammadi, A.A. Othman, A. Derdour and A. Mami, Asian J. Chem., 2010, 22, 5535-5542.         [ Links ]

49 M. Belkadi and A.A. Othman, Trends Applied Sci. Res., 2011, 6, 17-30.         [ Links ]

50 J.A. Karlowsky and M.E. Jones, J. Antimicrob. Chemother., 2003, 51, 467-468.         [ Links ]

51 M.E. Jones, J.A. Karlowsky, R. Blosser-Middleton, I. Critchley, E. Karginova, C. Thornsberry and D.F. Sahm, Antimicrob. Agents Chemother., 2003, 47, 830.         [ Links ]

52 C.W. Robert in Handbook of Chemistry andPhysics, 63/e, CRC Press, Inc., Florida, 1982-1983, C- 529.         [ Links ]

53 B.S. Furniss, A.J. Hannford, P.W.G. Smith and A.R. Tatchell, Vogel'sText Book of Practical Organic Chemistry, 5/e, Longman Scientific & Technical, New York, 1989, 647.         [ Links ]

 

 

Received 22 February 2011
Revised 17 May 2011
Accepted 22 January 2012

 

 

* To whom correspondence should be addressed. E-mail: adelaliothman@gmail.com

Creative Commons License Todo el contenido de esta revista, excepto dónde está identificado, está bajo una Licencia Creative Commons