Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Author(s): Amol Kale*, Rajendra Kakde, Smita Pawar and Rutuja Thombare

DOI: 10.2174/1389557521666201222145236

DownloadDownload PDF Flyer Cite As
Recent Development in Substituted Benzothiazole as an Anticonvulsant Agent

Page: [1017 - 1024] Pages: 8

  • * (Excluding Mailing and Handling)

Abstract

Heterocyclic compounds and their derivatives gained more attention due to their valuable biological and pharmacological properties. Benzothiazole is a heterocyclic structure containing a bicyclic ring system with a large panel of applications. The benzothiazole is present in many new products undergoing research hoping that it possesses various biological activities.

Epilepsy is a diverse group of diseases marked by neuronal excitability and hypersynchronous neuronal activity of motor, sensory or autonomic events with or without loss of consciousness.

Presently, many antiepileptic drugs like lamotrigine, stiripentol tiagabine, pregabalin, felbamate, and topiramate are available and effective towards 60-80% of patients only, along with undesirable side effects, such as hepatotoxicity, gastrointestinal disturbance, drowsiness, gingival hyperplasia, and hirsutism. Thus, many attempts are still on-going to develop antiepileptic drugs with a safer profile.

This review is mainly focused on the compilation of reported scientific literature data in the recent one-decade on the anticonvulsant activity of benzothiazole compounds.

Keywords: Benzothiazole, substituted benzothiazoles, anticonvulsant agent, anticonvulsant, pharmacophore, seizures.

Graphical Abstract

[1]
Tariq, S.; Kamboj, P.; Amir, M. Therapeutic advancement of benzothiazole derivatives in the last decennial period. Arch. Pharm. (Weinheim), 2019, 352(1)1800170
[http://dx.doi.org/10.1002/ardp.201800170] [PMID: 30488989]
[2]
Mohd, A.; Asif, S.; Ali, I. Hassan MohdZ. Synthesis of benzothiazole derivatives having acetamido and carbothioamido pharmacophore as anticonvulsant agents. Med. Chem. Res., 2012, 21(9), 2661-2670.
[http://dx.doi.org/10.1007/s00044-011-9791-1]
[3]
Sahu, P.K.; Sahu, P.K.; Lal, J.; Thavaselvam, D.; Agarwal, D.D. A facile green synthesis and in vitro antimicrobial activity 4H-pyrimido[2,1-b][1,3]benzothiazole derivatives using aluminum trichloride under solvent free conditions. Med. Chem. Res., 2012, 21(11), 3826-3834.
[http://dx.doi.org/10.1007/s00044-011-9908-6]
[4]
Wang, Z.; Shi, X-H.; Wang, J.; Zhou, T.; Xu, Y-Z.; Huang, T-T.; Li, Y.F.; Zhao, Y.L.; Yang, L.; Yang, S.Y.; Yu, L.T.; Wei, Y.Q. Synthesis, structure-activity relationships and preliminary antitumor evaluation of benzothiazole-2-thiol derivatives as novel apoptosis inducers. Bioorg. Med. Chem. Lett., 2011, 21(4), 1097-1101.
[http://dx.doi.org/10.1016/j.bmcl.2010.12.124] [PMID: 21262571]
[5]
Ammazzalorso, A.; Giancristofaro, A.; D’Angelo, A.; Filippis, B.D.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Amoroso, R. Benzothiazole-based N-(phenylsulfonyl)amides as a novel family of PPARα antagonists. Bioorg. Med. Chem. Lett., 2011, 21(16), 4869-4872.
[http://dx.doi.org/10.1016/j.bmcl.2011.06.028] [PMID: 21742490]
[6]
Pereira, G.A.; Massabni, A.C.; Castellano, E.E.; Costa, L.A.S.; Leite, C.Q.F.; Pavan, F.R. A broad study of two new promising antimycobacterial drugs: Ag(I) and Au(I) complexes with 2-(2-thienyl)benzothiazole. Polyhedron, 2012, 38(1), 291-296.
[http://dx.doi.org/10.1016/j.poly.2012.03.016]
[7]
Shafi, S.; Alam, M.M.; Mulakayala, N.; Mulakayala, C.; Vanaja, G.; Kalle, A.M.; Pallu, R.; Alam, M.S. Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities. Eur. J. Med. Chem., 2012, 49, 324-333.
[http://dx.doi.org/10.1016/j.ejmech.2012.01.032] [PMID: 22305614]
[8]
Liu, D-C.; Zhang, H-J.; Jin, C-M.; Quan, Z-S. Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents. Molecules, 2016, 21(3), 164.
[http://dx.doi.org/10.3390/molecules21030164] [PMID: 26938519]
[9]
Siddiqui, N.; Rana, A.; Khan, S.A.; Bhat, M.A.; Haque, S.E. Synthesis of benzothiazole semicarbazones as novel anticonvulsants--the role of hydrophobic domain. Bioorg. Med. Chem. Lett., 2007, 17(15), 4178-4182.
[http://dx.doi.org/10.1016/j.bmcl.2007.05.048] [PMID: 17572089]
[10]
Navale, A.; Pawar, S.; Deodhar, M.; Kale, A. Synthesis of substituted benzo[d]thiazol-2-ylcarbamates as potential anticonvulsants. Med. Chem. Res., 2013, 22(9), 4316-4321.
[http://dx.doi.org/10.1007/s00044-012-0434-y]
[11]
Ugale, V.G.; Patel, H.M.; Wadodkar, S.G.; Bari, S.B.; Shirkhedkar, A.A.; Surana, S.J. Quinazolino-benzothiazoles: Fused pharmacophores as anticonvulsant agents. Eur. J. Med. Chem., 2012, 53, 107-113.
[http://dx.doi.org/10.1016/j.ejmech.2012.03.045] [PMID: 22534186]
[12]
Singh, R.; Sharma, S. Synthesis, characterization and evaluation of 2-imino benzothiazole derivatives as anticonvulsant agents. Int. J. Pharm. Sci. Res., 2014, 5(05), 213-217.
[13]
Siddiqui, N.; Rana, A.; Khan, S.; Haque, S.; Arshad, M.; Ahmed, S. Synthesis and preliminary screening of benzothiazol-2-yl thiadiazole derivatives for anticonvulsant activity. Acta Pharm., 2009, 59(4), 441-451.https://content.sciendo.com/doi/10.2478/v10007-009-0031-x
[14]
Siddiqui, N.; Ahuja, P.; Malik, S.; Arya, S.K. Design of benzothiazole-1,3,4-thiadiazole conjugates: Synthesis and anticonvulsant evaluation. Arch. Pharm. (Weinheim), 2013, 346(11), 819-831.
[http://dx.doi.org/10.1002/ardp.201300083] [PMID: 24081512]
[15]
Siddiqui, N.; Rana, A.; Khan, S.A.; Haque, S.E.; Alam, M.S.; Ahsan, W.; Ahmed, S. Synthesis of 8-substituted-4-(2/4-substituted phenyl)-2H-[1,3,5]triazino[2,1-b][1,3]benzothiazole-2-thiones and their anticonvulsant, anti-nociceptive, and toxicity evaluation in mice. J. Enzyme Inhib. Med. Chem., 2009, 24(6), 1344-1350.
[http://dx.doi.org/10.3109/14756360902888176] [PMID: 19912067]
[16]
Choudhary, S.; Kalra, N.; Jeyabalan, G. Synthesis, characterization and pharmacological evaluation of some newer benzothiazole derivatives. Indian J. Pharm. Biol. Res., 2018, 6(02), 31-36.
[http://dx.doi.org/10.30750/ijpbr.6.2.6]
[17]
Siddiqui, N.; Pandeya, S.N.; Khan, S.A.; Stables, J.; Rana, A.; Alam, M.; Arshad, M.F.; Bhat, M.A. Synthesis and anticonvulsant activity of sulfonamide derivatives-hydrophobic domain. Bioorg. Med. Chem. Lett., 2007, 17(1), 255-259.
[http://dx.doi.org/10.1016/j.bmcl.2006.09.053] [PMID: 17046248]
[18]
Raju, G.N. Synthesis and anticonvulsant activity of newer benzothiazole derivatives. World J. Pharm. Pharm. Sci., 2017, 1701-1713.
[http://dx.doi.org/10.20959/wjpps20174-8963]
[19]
Khokra, S.L.; Arora, K.; Khan, S.A.; Kaushik, P.; Saini, R.; Husain, A. Synthesis, computational studies and anticonvulsant activity of novel benzothiazole coupled sulfonamide derivatives. Iran. J. Pharm. Res., 2019, 18(1), 1-15.
[PMID: 31089339]
[20]
Liu, D-C.; Deng, X-Q.; Wang, S-B.; Quan, Z-S. Synthesis and anticonvulsant activity evaluation of 7-alkoxy[1,2,4]triazolo[3,4-b]benzothiazol-3(2H)-ones. Arch. Pharm. (Weinheim), 2014, 347(4), 268-275.
[http://dx.doi.org/10.1002/ardp.201300277] [PMID: 24448887]
[21]
Siddiqui, N.; Rana, A.; Khan, S.A.; Haque, S.E.; Alam, M.S.; Ahsan, W. Anticonvulsant and toxicity evaluation of newly synthesized 1-[2-(3,4-disubstituted phenyl) -3-chloro-4-oxoazetidin-1-yl]-3-(6-substituted -1,3-benzothiazol-2-yl)ureas. Acta Chim. Slov., 2009, 56, 462-469.
[22]
Amnerkar, N.D.; Bhusari, K.P. Synthesis, anticonvulsant activity and 3D-QSAR study of some prop-2-eneamido and 1-acetyl-pyrazolin derivatives of aminobenzothiazole. Eur. J. Med. Chem., 2010, 45(1), 149-159.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.037] [PMID: 19853976]
[23]
Malik, S.; Bahare, R.S.; Khan, S.A. Design, synthesis and anticonvulsant evaluation of N-(benzo[d]thiazol-2-ylcarbamoyl)-2-methyl-4-oxoquinazoline-3(4H)-carbothioamide derivatives: A hybrid pharmacophore approach. Eur. J. Med. Chem., 2013, 67, 1-13.
[http://dx.doi.org/10.1016/j.ejmech.2013.06.026] [PMID: 23831504]
[24]
Siddiqui, N.; Alam, M.S.; Sahu, M.; Naim, M.J.; Yar, M.S.; Alam, O. Design, synthesis, anticonvulsant evaluation and docking study of 2-[(6-substituted benzo[d]thiazol-2-ylcarbamoyl)methyl]-1-(4-substituted phenyl)isothioureas. Bioorg. Chem., 2017, 71, 230-243.
[http://dx.doi.org/10.1016/j.bioorg.2017.02.009] [PMID: 28238402]
[25]
Tripathi, L.; Juneja, R. Synthesis and anticonvulsant evaluation of benzothiazole derivatives. MIT Int. J. Pharm. Sci., 2015, 1(2), 26-30.
[26]
Hassan, M.Z.; Khan, S.A.; Amir, M. Design, synthesis and evaluation of N-(substituted benzothiazol-2-yl)amides as anticonvulsant and neuroprotective. Eur. J. Med. Chem., 2012, 58, 206-213.
[http://dx.doi.org/10.1016/j.ejmech.2012.10.002] [PMID: 23124217]