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Synthesis of Some New N-Alkyl/Aralkyl-N-(2,3-Dihydro-1,4-Benzodioxin-6-YL)-4-Bromobenzenesulfonamides as Possible Therapeutic Agents F or Alzheimer’s Disease

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Pharmaceutical Chemistry Journal Aims and scope

The present work summarizes the synthesis of new sulfonamides and their N-substituted derivatives as possible agents for treating Alzheimer’s disease. The synthesis was triggered by reaction of 1,4-benzodioxane-6- amine (1) with 4-bromobenzenesulfonyl chloride (2) in aqueous alkaline media to yield N-(2,3-dihydro-1,4- benzodioxin-6-yl)-4-bromobenzenesulfonamide (3), which was further treated with different alkyl/aralkyl halides (4a–4n) using N,N-dimethylformamide (DMF) as reaction medium in the presence of lithium hydride (LiH) as a base to yield N-alkyl/aralkyl-N-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-bromobenzenesulfonamides 5a–5n. The structures of all synthesized derivatives were confirmed by spectroscopic techniques including IR, 1H NMR and EI-MS. All the cholinesterase enzyme inhibitors are good agents for treating Alzheimer’s disease. The inhibition activity of synthesized molecules was studied so as to assess their possible therapeutic effect on this disease.

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References

  1. A. Shaabani, E. Soleimani and A. H. Rezayan, Tetrahedron. Lett., 48(12), 2185 – 2188 (2007).

    Article  CAS  Google Scholar 

  2. Y. Kanda, Y. Kawanishi, K. Oda, et al, Bioorg. Med. Chem., 9(4), 897 – 907 (2001).

    Article  CAS  PubMed  Google Scholar 

  3. U. O. Ozdemir, P. Guvenc, E. Sahin, et al., Inorg.. Chim. Acta., 362(8), 2613 – 2618 (2009).

    Article  CAS  Google Scholar 

  4. M. Irshad, M. A. Abbasi, Aziz-ur-Rehman, et al., J. Chem. Soc. Pak., 36(4), 660 – 673 (2014).

    CAS  Google Scholar 

  5. M. A. Abbasi, Aziz-ur-Rehman, T. Muhmood, et al., J. Chem. Soc. Pak., 35(2), 404 – 410 (2013).

    Google Scholar 

  6. A. Husain, Acta. Polon. Pharm., 66(5), 513 – 521 (2009).

    CAS  Google Scholar 

  7. X. Deng and N. S. Mani, Green Chem., 8(9), 835 – 838 (2006).

    Article  CAS  Google Scholar 

  8. M. A. Abbasi, S. Najm, Aziz-ur-Rehman, et al., Trop. J. Pharm. Res., 14(1), 47 – 54 (2015).

    Article  Google Scholar 

  9. M. Remko and C. W. V. D. Leith, Bioorg. Med. Chem., 12(20), 5395 – 5403 (2004).

    Article  CAS  PubMed  Google Scholar 

  10. M. Irshad, M. A. Abbasi, Aziz-ur-Rehman, et al., Asian J. Chem., 26(4), 1151 – 1160 (2014).

    Article  CAS  Google Scholar 

  11. W. R. Roush, S. L. Gwaltney, and J. Cheng, J. Am. Chem. Soc., 120(42), 10994 – 10995 (1998).

    Article  CAS  Google Scholar 

  12. W. R. Roush, J. Cheng, B. K. Reed, et al., Bioorg. Med. Chem. Lett., 11(20), 2759 – 2762 (2001).

    Article  CAS  PubMed  Google Scholar 

  13. M. A. Abbasi, Aziz-ur-Rehman, M. Z. Qureshi, et al., Braz. J. Pharm. Sci., 49(1), 127 – 133 (2013).

    Article  CAS  Google Scholar 

  14. M. A. Abbasi, S. Ahmad, Aziz-ur-Rehman, et al., Trop. J. Pharm. Res., 13(5), 739 – 745 (2014).

    Article  CAS  Google Scholar 

  15. M. A. Abbasi, A. Saeed, Aziz-ur-Rehman, et al., Iran. J. Pharm. Res., 13(1), 87 – 94 (2014).

    CAS  PubMed  PubMed Central  Google Scholar 

  16. G. L. Ellman, K. D. Courtney, V. Andres Jr., et al., Biochem. Pharmacol., 7(2), 88 – 95 (1961).

    Article  CAS  PubMed  Google Scholar 

Download references

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Authors and Affiliations

  1. Department of Chemistry, Government College University, -54000, Lahore, Pakistan

    M. A. Abbasi,  Aziz-ur-Rehman, S. Z. Siddiqui & M. Nazir

  2. Hamdard Institution of Pharmaceutical Sciences, Hamdard University Islamabad Campus, Islamabad, Pakistan

    A. Anum

  3. Department of Chemistry, The Islamia University of Bahawalpur, -63100, Bahawalpur, Pakistan

    M. Ashraf & A. Noreen

  4. Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

    S. A. A. Shah

  5. Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

    S. A. A. Shah

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  1. M. A. Abbasi
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Correspondence to M. A. Abbasi.

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Abbasi, M.A., Anum, A., Aziz-ur-Rehman et al. Synthesis of Some New N-Alkyl/Aralkyl-N-(2,3-Dihydro-1,4-Benzodioxin-6-YL)-4-Bromobenzenesulfonamides as Possible Therapeutic Agents F or Alzheimer’s Disease. Pharm Chem J 56, 61–70 (2022). https://doi.org/10.1007/s11094-022-02598-y

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  • DOI: https://doi.org/10.1007/s11094-022-02598-y

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