Advertisement

Russian Journal of Bioorganic Chemistry

, Volume 42, Issue 2, pp 198–209 | Cite as

Synthesis of some new N-substituted-N-(2,3-Dihydro-[1,4]benzodioxin-6-yl)-4-acetamidobenzenesulfonamides as valuable antibacterial agents

  • M. A. AbbasiEmail author
  • S. Tariq
  • Aziz-ur-Rehman
  • S. Z. Siddiqui
  • I. Ahmad
  • R. Malik
  • S. A. A. Shah
Article

Abstract

The aim of the research was to investigate the anti-bacterial potential of some N-substituted sulfonamides bearing benzodioxane moiety. The synthesis was started by reaction of N-2,3-dihydrobenzo[1,4]dioxin-6-amine with 4-acetamidobenzene-1-sulfonyl chloride in the presence of 10% aqueous Na2CO3 solution to yield N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-acetamidobenzenesulfonamide, which was further reacted with alkyl/aralkyl halides in DMF and lithium hydride as a base to afford N-substituted-N-(2,3dihydro-[1,4]-benzodioxin-6-yl)-4-acetamidobenzenesulfonamides. All the synthesized compounds were characterized by spectral data (IR, 1H NMR, EI-MS, and HR-MS). The compounds were tested for antibacterial activity and most of them exhibited potent therapeutic potential against various Gram-negative and Gram-positive strains.

Keywords

N-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-4-acetamidobenzenesulfonamide alkyl/aralkyl halides spectral analysis antibacterial activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Dauban, P. and Dodd, R.H., Org. Lett., 2000, vol. 2, pp. 2327–2329.CrossRefPubMedGoogle Scholar
  2. 2.
    Roush, W.R., Cheng, J., Knapp-Reed, B., AlvarezHernandez, A., McKerrow, J.H., Hansell, E., and Engel, J.C., J. Am. Chem. Soc., 1998, vol. 120, pp. 10994–10995.CrossRefGoogle Scholar
  3. 3.
    Tougu, V., Curr. Med. Chem., 2001, vol. 1, pp. 155–170.Google Scholar
  4. 4.
    Hartman, G.D., Halczenko, W., Prugh, J.D., Smith, R.L., Sugrue, M.F., Mallorga, P., Michelson, S.R., Randall, W.C., Schwam, H., and Sondey, J.M., J. Med. Chem., 1992, vol. 35, pp. 3027–3033.CrossRefPubMedGoogle Scholar
  5. 5.
    Cremlyn, R., An Introduction to Sulphur Chemistry, New York: Wiley, 1996.Google Scholar
  6. 6.
    Lukin, O., Gramlich, V., Kandre, R., Zhun, I., Felder, T., Schalley, C.A., and Dolgonos, G., J. Am. Chem. Soc., 2008, vol. 128, pp. 8964–8974.CrossRefGoogle Scholar
  7. 7.
    Isik, K. and Kocak, F.O., Microbiol. Res., 2009, vol. 164, pp. 49–58.CrossRefPubMedGoogle Scholar
  8. 8.
    Caballero, D., Torres-Lapasio, J.R., Baeza-Baeza, J.J., and Garcia-Alvarez-Coque, M.C., J. Liq. Chromatogr. Rel. Technol., 2001, vol. 24, pp. 117–131.CrossRefGoogle Scholar
  9. 9.
    Mallesha, L. and Mohana, K.N., Eur. J. Chem., 2011, vol. 2, pp. 193–199.CrossRefGoogle Scholar
  10. 10.
    Vazquez, M.T., Rosell, G., and Pujol, M.D., Eur. J. Med. Chem., 1997, vol. 32, pp. 529–534.CrossRefGoogle Scholar
  11. 11.
    Ahmed, A., Khan, S.A., and Alam, T., Pharmazie, 2003, vol. 58, pp. 173–176.PubMedGoogle Scholar
  12. 12.
    Chapleo, C.B., Myers, P.L., Butler, C.M., Doxey, J.C., Roach, A.G., and Smith, C.F.C., J. Med. Chem., 1983, vol. 26, pp. 823–831.CrossRefPubMedGoogle Scholar
  13. 13.
    Khan, S.A., Ahmed, B., and Alam, T., Pak. J. Pharm. Sci., 2006, vol. 19, pp. 290–294.PubMedGoogle Scholar
  14. 14.
    Davis-Searles, P.R, Nakanishi, Y., Kim, N.C., Graf, T.N., Oberlies, N.H., and Wani, M.C., Cancer Res., 2005, vol. 65, pp. 4448–4457.CrossRefPubMedGoogle Scholar
  15. 15.
    Arai, A., Kessler, M., and Xiao, P., Brain Res., 1994, vol. 638, pp. 343–346.CrossRefPubMedGoogle Scholar
  16. 16.
    Neill, M.J.O., Bleakman, D., and Zimmerman, D.M., Curr. Drug Targets: CNS Neurol. Disord., 2004, vol. 3, pp. 181–194.Google Scholar
  17. 17.
    Avihai, Y., Rachel, O., Tzofit, K., Sima M., Daniel, S., Alex, A., Alina, S., Efrat, B.Z., Nili, S., Osnat, B.K., Alexander, K., Vered, B., and Oren, M.B., Bioorg. Med. Chem. Lett., 2012, vol. 22, pp. 6460–6468.CrossRefGoogle Scholar
  18. 18.
    Martin, J.W., Kyle, R.B., Henrike, V., James, M.B., Thomas, D., William, L., Lewis, C.C., William, J.I., Matthew, G.V.H., Min, S., Douglas, S.A., Craig, J.T., and Matthew, B.B., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 6322–6327.CrossRefGoogle Scholar
  19. 19.
    Irshad, M., Abbasi, M.A., Aziz-Ur-Rehman, Siddiqui, S.Z., Ashraf, M., Ejaz, S.A., Lodhi, M.A., and Jamal, S.B., J. Chem. Soc. Pak., 2014, vol. 36, pp. 660–673.Google Scholar
  20. 20.
    Doran, K., Jihae, B., Jiho, S., Hyeyoung, B., Hyeyoung, M., and Kyung, H.M., Bioorg. Med. Chem. Lett., 2014, vol. 24, pp. 3823–3825.CrossRefGoogle Scholar
  21. 21.
    Kaspady, M., Narayanaswamy, V.K., Raju, M., and Rao, G.K., Lett. Drug Des. Discov., 2009, vol. 6, pp. 21–28.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2016

Authors and Affiliations

  • M. A. Abbasi
    • 1
    Email author
  • S. Tariq
    • 1
  • Aziz-ur-Rehman
    • 1
  • S. Z. Siddiqui
    • 1
  • I. Ahmad
    • 2
  • R. Malik
    • 2
  • S. A. A. Shah
    • 3
    • 4
  1. 1.Department of ChemistryGovernment College UniversityLahorePakistan
  2. 2.Department of Pharmacythe Islamia University of BahawalpurBahawalpurPakistan
  3. 3.Faculty of PharmacyUniversity Technology MARA, Puncak Alam Campus42300Bandar Puncak Alam, Selangor Darul EhsanMalaysia
  4. 4.Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3University Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak AlamSelangor Darul EhsanMalaysia

Personalised recommendations