Synthesis and Characterization of Novel Hybrid Sulfonamide Molecules with Benzothiazole Scaffold

Year 2022, , 899 - 907, 01.06.2022

Erbay Kalay

https://doi.org/10.21597/jist.1039476

Cited By: 1

Abstract

Benzothiazole-based compounds have a wide spectrum of pharmacological activities such as anticancer, anti-diabetic, anticonvulsant, antiviral, antituberculous, antimalarial, analgesic, anti-inflammatory, antimicrobial, and fungicidal. On the other hand, compounds bearing a sulfonamide group are used to inhibit some enzymes such as carbonic anhydrase, HIV protease, cysteine protease and cyclooxygenase (COX-II) apart from their commercial applications as antibacterial/antibiotics. Due to the wide variety of biological activities of benzothiazole and sulfonamide scaffolds, the presence of such pharmacophores in synthetic organic compounds has aroused great interest in medicinal chemists. Recently, molecular hybrids have been envisaged by combining at least two pharmacophore-specific moieties to modulate multiple disease targets simultaneously. Molecular hybridization design appears to be a novel approach to develop multifunctional hybrid molecules that involve combining at least two pharmacophores in a scaffold. In this study, benzothiazole-based bissulfonamide 8a-b and sulfonamide-amide 7a-c hybrid compounds, which have the potential to be used in many different therapeutic applications, were synthesized effectively after a series of reactions starting from the 2-amino benzothiazole compound. The structures of the synthesized novel hybrid molecules 7a-c, 8a-b were elucidated by 1H, 13C NMR, FTIR and HRMS spectroscopy techniques.

Keywords

benzothiazole, sulfonamide, hybrid compound

References

• Abbot V, Sharma, P, Dhiman S, Noolvi MN, Patel HM, Bhardwaj V, 2017. Small hybrid heteroaromatics: resourceful biological tools in cancer research. RSC Advances, 7: 28313–28349.
• Adkins JC, Faulds D, 1998. Amprenavir. Drugs, 55(6): 837-842.
• Aggarwal M, Kondeti B, McKenna R, 2013. Anticonvulsant/antiepileptic carbonic anhydrase inhibitors: a patent review. Expert Opinion on Therapeutic Patents, 23: 717-724.
• Azzam RA, Elboshi, HA, Elgemeie GH, 2020. Novel Synthesis and Antiviral Evaluation of New Benzothiazole Bearing N Sulfonamide 2 Pyridone Derivatives as USP7 Enzyme Inhibitors. ACS Omega, 5: 30023−30036.
• Carta F, Supuran CT, 2013. Diuretics with carbonic anhydrase inhibitory action: a patent and literature review (2005-2013). Expert Opinion on Therapeutic Patents, 23: 681-691.
• Gulçin İ, Taslimi P, 2018. Sulfonamide inhibitors: a patent review 2013-present. Expert Opinion on Therapeutic Patents, 28: 541-549.
• Ivasiv V, Albertini C, Gonçalves AE, Rossi M, Bolognesi ML, 2019. Molecular hybridization as a tool for designing multitarget drug candidates for complex diseases. Current Topics in Medicinal Chemistry, 19: 1694-1711.
• Keri RS, Patil MR, Patil SA, Budagumpi S, 2015. A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry, European Journal of Medicinal Chemistry, 89, 207-251.
• Kerru N, Singh P, Koorbanally N, Raj R, Kumar V, 2017. Recent advances (2015–2016) in anticancer hybrids. European Journal of Medicinal Chemistry, 142: 179–212.
• Lin SJ, Tsai WJ, Chiou WF, Yang TH, Yang LM, 2008. Selective COX-2 inhibitors. Part 2: Synthesis and biological evaluation of 4-benzylideneamino-and 4-phenyliminomethyl-benzenesulfonamides. Bioorganic & Medicinal Chemistry, 16: 2697–2706.
• Luci DK, Jameson JB, Yasgar A, Diaz G, Joshi N, Kantz A, Markham K, Perry S, Kuhn N, Yeung J, Kerns EH, Schultz L, Holinstat M, Nadler JL, Taylor-Fishwick DA, Jadhav A, Simeonov A, Holman TR, Maloney DJ, 2014. Synthesis and Structure-Activity Relationship Studies of 4 ((2- Hydroxy-3-methoxybenzyl)amino) benzenesulfonamide Derivatives as Potent and Selective Inhibitors of 12-Lipoxygenase. Journal of Medicinal Chemistry, 57: 495−506.
• Lyseng-Williamson KA, Yang LPH, 2008. Spotlight on Topiramate in Epilepsy. CNS Drugs, 22: 171-174. Murata M, Horiuchi E, Kanazawa I, 2001. Zonisamide has beneficial effects on Parkinson's disease patients. Neuroscience Research, 41: 397-399.
• Naaz F, Srivastava R, Singh A, Singh N, Verma, R, Singh, VK, Singh RK, 2018. Molecular modeling, synthesis, antibacterial and cytotoxicity evaluation of sulfonamide derivatives of benzimidazole, indazole, benzothiazole andthiazole. Bioorganic & Medicinal Chemistry, 26: 3414–3428.
• Nishimoria I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT, 2005. Carbonic anhydrase inhibitors: Inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorganic & Medicinal Chemistry Letters, 15: 3828-3833.
• Rouf A, Tanyeli C, 2015. Bioactive thiazole and benzothiazole derivatives. European Journal of Medicinal Chemistry, 97, 911-927.
• Sandhu S, Bansal Y, Silakari O, Bansal G, 2014. Coumarin hybrids as novel therapeutic agents. Bioorganic & Medicinal Chemistry, 22: 3806–3814.
• Supuran CT, Nicolae A, Popescu A, 1996. Carbonic anhydrase inhibitors. Part 35. Synthesis of Schiff bases derived from sulfanilamide and aromatic aldehydes: the first inhibitors with equally high affinity towards cytosolic and membrane-bound isozymes. European Journal of Medicinal Chemistry, 31: 431-438.
• Supuran CT, Scozzafava A, 2000. Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opinion on Therapeutic Patents, 10: 575–600.
• Supuran CT, Scozzafava A, 2000. Carbonic anhydrase inhibitors-Part 94. 1,3,4-Thiadiazole-2-sulfonamide derivatives as antitumor agents? European Journal of Medicinal Chemistry, 35: 867-874.
• Supuran CT, Scozzafava A, 2001. Carbonic Anhydrase Inhibitors. Current Medicinal Chemistry, 363: 61-97.
• Supuran CT, Scozzafava A, 2007. Carbonic anhydrases as targets for medicinal chemistry. Bioorganic & Medicinal Chemistry. 15: 4336–4350.
• Wong D, Wang M, Cheng Y, Gerald GAF, 2005. Cardiovascular hazard and non-steroidal anti-inflammatory drugs. Current Opinion in Pharmacology, 5: 2014-210.