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Vol. 33 No. 12 (2021): Vol 33 Issue 12, 2021

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Synthesis and Evaluation of Antiepileptic Activity of Newly Designed Coumarin-Sulfonamide Hybrids

https://doi.org/10.14233/ajchem.2021.23527
Arti Gupta
Amity Institute of Pharmacy, Amity University, Noida-201301, India ; Lloyd School of Pharmacy, Plot No. 3, Knowledge Park-2, Greater Noida-201306, India
Sandeep Kumar
School of Pharmacy, Sharda University, Plot No. 32, 43, Knowledge Park III, Greater Noida-201310, India
Vijay Kumar Singh
Department of Pharmacy, Galgotias University, Greater Noida-201310, India
B.P. Mallikarjun
IIMT College of Pharmacy, Plot No. 19 & 20, Knowledge Park III, Greater Noida-201310, India
Neerupma Dhiman
Amity Institute of Pharmacy, Amity University, Noida-201301, India
Archana Sharma
Amity Institute of Pharmacy, Amity University, Noida-201301, India

Corresponding Author(s) : Neerupma Dhiman

ndhiman@amity.edu

Asian Journal of Chemistry, Vol. 33 No. 12 (2021): Vol 33 Issue 12, 2021

Abstract

The combination of different heterocyclic rings to form a multifunctional compound is a new approach to get the potent and selective compounds, which can act as antiepileptic drugs. In this study we designed and synthesized the hybrid of the coumarin ring with sulfonamide moiety. Coumarin sulfonamide hybrids (CS1-CS7) were synthesized by Knoevenagel condensation of methyl anilinosulfonyl acetate with substituted salicyaldehyde in the presence of catalytic base. The synthesized hybrid compounds were characterized by means of mass, 1H & 13C NMR and FTIR spectroscopy, moreover antiepileptic activity was screened through seizure model of epilepsy using pentylenetetrazole and maximal electroshock. According to results, compound CS-2 remained to be highest potent and presented significant protection at 60 mg/kg in both the seizure models. Furthermore, compound CS-2 was also evaluated for biochemical and a histopathological study in which no significant results were obtained. In addition to former activities, compound CS-2 was also examined for liver toxicity.

Keywords

Coumarin Sulfonamide Knoevenagel condensation Salicyaldehyde Anilinosulfonyl acetate Antiepileptic activity
Gupta, A., Kumar, S., Kumar Singh, V., Mallikarjun, B., Dhiman, N., & Sharma, A. (2021). Synthesis and Evaluation of Antiepileptic Activity of Newly Designed Coumarin-Sulfonamide Hybrids. Asian Journal of Chemistry, 33(12), 3108–3114. https://doi.org/10.14233/ajchem.2021.23527
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References
  1. S. Song, L. Luo, B. Sun and D. Sun, Glia, 68, 472 (2020); https://doi.org/10.1002/glia.23699
  2. C.T. Supuran, Clin. Sci., 135, 1233 (2021); https://doi.org/10.1042/CS20210040
  3. S. Thouta, Y. Zhang, E. Garcia and T.P. Snutch, Sci. Rep., 11, 15180 (2021); https://doi.org/10.1038/s41598-021-94633-3
  4. T. Auer, P. Schreppel, T. Erker and C. Schwarzer, Pharmacol. Ther., 205, 107422 (2020); https://doi.org/10.1016/j.pharmthera.2019.107422
  5. T.H. Maren, Physiol. Rev., 47, 595 (1967); https://doi.org/10.1152/physrev.1967.47.4.595
  6. W.H. Abd-Allah, E.E.A. Osman, M.A.E.M. Anwar, H.N. Attia and S.M. El Moghazy, Bioorg. Chem., 98, 103738 (2020); https://doi.org/10.1016/j.bioorg.2020.103738
  7. A.M. Aribi and J.L. Stringer, Epilepsy Res., 49, 143 (2002); https://doi.org/10.1016/S0920-1211(02)00019-0
  8. Z.Q. Xiong and J.L. Stringer, Brain Res. Dev. Brain Res., 122, 113 (2000); https://doi.org/10.1016/S0165-3806(00)00057-2
  9. J.L. Stringer and E.W. Lothman, Brain Res. Dev. Brain Res., 91, 136 (1996); https://doi.org/10.1016/0165-3806(95)00165-4
  10. E.W. Lothman and R.C. Collins, Brain Res., 218, 299 (1981); https://doi.org/10.1016/0006-8993(81)91308-1
  11. B. Malawska, Front. Med. Chem., 4, 805 (2009); https://doi.org/10.2174/978160805207310904010805
  12. B. Masereel, S. Rolin, F. Abbate, A. Scozzafava and C.T. Supuran, J. Med. Chem., 45, 312 (2002); https://doi.org/10.1021/jm0109199
  13. A. Thiry, J.-M. Dogne, C. Supuran and B. Masereel, Curr. Top. Med. Chem., 7, 855 (2007); https://doi.org/10.2174/156802607780636726
  14. N. Siddiqui, M.F. Arshad and S.A. Khan, Acta Pol. Pharm. Drug Res., 66, 161 (2009).
  15. J. Jumal, Sci. Heal. Technol., 7, 62 (2021); https://doi.org/10.33102/mjosht.v7i1.145
  16. S. Partap, M.S. Yar, M.Z. Hassan, M.J. Akhtar and A.A. Siddiqui, Arch. Pharm., 350, 1700135 (2017); https://doi.org/10.1002/ardp.201700135
  17. K. Kamiñski, A. Rapacz, J.J. £uszczki, G. Latacz, J. Obniska, K. KieæKononowicz and B. Filipek, Bioorg. Med. Chem., 23, 2548 (2015); https://doi.org/10.1016/j.bmc.2015.03.038
  18. R. Morphy and Z. Rankovic, J. Med. Chem., 48, 6523 (2005); https://doi.org/10.1021/jm058225d
  19. M. Sahu, N. Siddiqui, M.J. Naim, O. Alam, M.S. Yar, V. Sharma and S. Wakode, Arch. Pharm., 350, 1700146 (2017); https://doi.org/10.1002/ardp.201700146
  20. C.B. Mishra, S. Kumari, A. Angeli, S. Bua, R.K. Mongre, M. Tiwari and C.T. Supuran, J. Med. Chem., 64, 3100 (2021); https://doi.org/10.1021/acs.jmedchem.0c01889
  21. H.M. Alshibl, E.S. Al-Abdullah, M.E. Haiba, H.M. Alkahtani, G.E.A. Awad, A.H. Mahmoud, B.M.M. Ibrahim, A. Bari and A. Villinger, Molecules, 25, 3251 (2020); https://doi.org/10.3390/molecules25143251
  22. W.H. Abd-Allah, M.E. Aboutabl, M.N. Aboul-Enein and A.A.S. ElAzzouny, Bioorg. Chem., 71, 135 (2017); https://doi.org/10.1016/j.bioorg.2017.01.021
  23. M.E. Aboutabl, R.M. Hassan, A.A.-S. El-Azzouny, M.N. Aboul-Enein and W.H. Abd-Allah, Bioorg. Chem., 94,103473 (2020); https://doi.org/10.1016/j.bioorg.2019.103473
  24. O. Bedi and P. Krishan, Naunyn Schmiedebergs Arch. Pharmacol., 393, 565 (2020); https://doi.org/10.1007/s00210-019-01742-y
  25. K. Socala and P. Wlaz, Eds.: D. Vohora, Acute Seizure Tests Used in Epilepsy Research: Step-by-Step Protocol of the Maximal Electroshock Seizure (MES) Test, the Maximal Electroshock Seizure Threshold (MEST) Test, and the Pentylenetetrazole (PTZ)-Induced Seizure Test in Rodents, In: Experimental and Translational Methods to Screen
  26. Drugs Effective Against Seizures and Epilepsy. Neuromethods, Springer, vol. 167, pp. 79-102 (2021); https://doi.org/10.1007/978-1-0716-1254-5_5
  27. A.P. Nikalje, A. Ansari, S. Bari and V. Ugale, Arch. Pharm., 348, 433 (2015); https://doi.org/10.1002/ardp.201500020
  28. N.S. Reddy, M.R. Mallireddigari, S. Cosenza, K. Gumireddy, S.C. Bell, E.P. Reddy and M.V.R. Reddy, Bioorg. Med. Chem. Lett., 14, 4093 (2004); https://doi.org/10.1016/j.bmcl.2004.05.016
  29. J.N. Appaturi, R. Ratti, B.L. Phoon, S.M. Batagarawa, I.U. Din, M. Selvaraj and R.J. Ramalingam, Dalton Trans., 50, 4445 (2021); https://doi.org/10.1039/D1DT00456E
  30. N. Siddiqui, A. Rana, S.A. Khan, M.A. Bhat and S.E. Haque, Bioorg. Med. Chem. Lett., 17, 4178 (2007); https://doi.org/10.1016/j.bmcl.2007.05.048
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