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Syntheses and antibacterial studies of some 2-[5-(Aryl)-[1,3,4]oxadiazole-2-ylsulfanyl] alkanoic Acids

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Abstract

Some new 2-[5-(aryl)-[1,3,4]oxadiazole-2-ylsulfanyl]alkanoic acids were synthesized and studied for their antibacterial activity. These compounds were prepared from aromatic carboxylic acid hydrazides. Aromatic carboxylic acid hydrazides 1 on refluxing with carbon disulfide and methanolic potassium hydroxide and then on subsequent acidification with hydrochloric acid furnish 5-aryl-1,3,4-oxadiazole-2-thiones 2. 2-Chloro alkanoic acids react with 2 in alkaline media and on acidification yield the title compounds 3. These compounds were characterised by CHN analyses, IR, mass and 1H NMR spectral data. All the compounds were evaluated for their in vitro antibacterial activity against two Gram negative strains (Escherichia coli and Pseudomonas aeruginosa) and two Gram positive strains (Bacillus subtilis and Staphylococcus aureus) and their minimum inhibitory concentration (MIC) were determined.

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References

  1. M.G. Mamolo, D. Zampieri, L. Vio, M. Fermeglia, M. Ferrone, S. Pricl, G. Scialino, E. Banfi, Bioorg. Med. Chem. 13 (2005) 3797.

    CAS  Google Scholar 

  2. Y.A. Al-Soud, N.A. Al-masoudi, J. Braz. Chem. Soc. 14 (2003) 790.

    CAS  Google Scholar 

  3. S. Jain, N. Jain, P. Mishra, Indian J. Heterocyclic Chem. 14 (2005) 359.

    CAS  Google Scholar 

  4. H. El-Masry, H.H. Fahmy, S.H. Ali Abdel Wahed, Molecules. 5 (2000) 1429.

    CAS  Google Scholar 

  5. X.J. Zou, L.H. Lai, G.Y. Jin, Z.X. Zhang, J. Agric Food Chem. 50 (2002) 3757.

    CAS  Google Scholar 

  6. A. Shehata, Saudi Pharmaceutical Journal. 11 (2003) 87.

    CAS  Google Scholar 

  7. S. Holla, C.S. Prasanna, B. Poojary, K.S. Rao, K. Shridhara, U.G. Bhat, Indian J. Chem. 43 (2004) 864.

    Google Scholar 

  8. M.A. Shaban, A.Z. Nasr, S.M. El-badry, J. Islamic Acad. Sci. 4 (1991) 184.

    Google Scholar 

  9. S. Aboraia, H.M. Abdel-Rahman, N.M. Mahfouz, M.A. El-Gendy, Bioorg. Med. Chem. 14 (2006) 1236.

    CAS  Google Scholar 

  10. M.M. Burbuliene, V. Jakubkiene, G. Mekuskiene, E. Udrenaite, R. Smicius, P. Vainilavicius, Farmaco. 59 (2004) 767.

    CAS  Google Scholar 

  11. A. Foroumadi, Z. Kargar, A. Sakhteman, Z. Sharifzadeh, R. Feyzmohammadi, M. Kazemi, A. Shafiee, Bioorg. Med. Chem. Lett. 16 (2006) 1164.

    CAS  Google Scholar 

  12. A. Foroumadi, F. Soltani, H. Moallemzadeh-Haghighia, A. Shafiee, Arch. Pharm. Chem. Life Sci. 338 (2005) 112.

    CAS  Google Scholar 

  13. A. Foroumadi, Z. Kiani, F. Soltani, Farmaco 58 (2003) 1073.

    CAS  Google Scholar 

  14. A. Foroumadi, M. Mirzaei, A. Shafiee, Pharmazie 56 (2001) 610.

    CAS  Google Scholar 

  15. D.P. Pathak, N. Jain, P. Mishra, S. Jain, Indian J. Heterocyclic Chem. 14 (2005) 373.

    CAS  Google Scholar 

  16. D.P. Pathak, N. Jain, P. Mishra, S. Jain, Indian J. Heterocyclic Chem. 15 (2005) 177.

    CAS  Google Scholar 

  17. H.L. Yale, K. Loose, J. Martins, M. Holsing, F.M. Perry, J. Bernstein, J. Am. Chem. Soc. 75 (1953) 1933.

    CAS  Google Scholar 

  18. S. Jain, P. Mishra., Indian J. Heterocyclic Chem. 13 (2004) 307.

  19. J.G. Cappucino, N. Sherman, Microbiology- A Laboratory Manual, Addison Weslay Longman, Inc., Harlow, 1999.

    Google Scholar 

  20. Bauernfeind, J. Antimicrob. Chemother. 40 (1997) 639.

    CAS  Google Scholar 

  21. A.A. Hoogkamp-Korstanje, J. Antimicrob. Chemother. 40 (1997) 427.

    CAS  Google Scholar 

  22. D.J. Weber, S.M. Saviteer, W.A. Rutala, C.A. Thomann, Antimicrob. Agents Chemother. 32 (1988) 642.

    CAS  Google Scholar 

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Jain, N., Pathak, D.P., Mishra, P. et al. Syntheses and antibacterial studies of some 2-[5-(Aryl)-[1,3,4]oxadiazole-2-ylsulfanyl] alkanoic Acids. JICS 6, 77–81 (2009). https://doi.org/10.1007/BF03246504

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  • DOI: https://doi.org/10.1007/BF03246504

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