Synthesis and Characterization of Novel Hybrid Sulfonamide Molecules with Benzothiazole Scaffold

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

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