Synthesis of Some New Benzisothiazolone and Benzenesulfonamide Derivatives of Biological Interest Starting from Saccharin Sodium

• Published in: Archiv der Pharmazie (Weinheim) 2013-10, Vol.346 (10), p.733-742
• Main Author: El-Sabbagh, Osama I.
• Format: Article
• Language: English
• Subjects: Animals; Antiviral activity; Antiviral Agents - chemical synthesis; Antiviral Agents - chemistry; Antiviral Agents - pharmacology; Benzenesulfonamide; Benzenesulfonamides; Benzisothiazolone derivatives; Cell Line, Tumor; Cells, Cultured; Derivatives; Humans; Lung - cytology; Mice; Saccharin - chemistry; Saccharin sodium; Spectrum Analysis; Sulfonamides - chemical synthesis; Sulfonamides - chemistry; Sulfonamides - pharmacology; Synthesis; Thiazoles - chemical synthesis; Thiazoles - chemistry; Thiazoles - pharmacology; Viruses - drug effects
• ISSN: 0365-6233; 1521-4184
• DOI: 10.1002/ardp.201300110

Two new series of benzenesulfonamide (4a–f, 5a–b, 6, 7) and 1,2‐benzisothiazol‐3(2H)‐one‐1,1‐dioxide (9a–c, 10, 12a–d) derivatives were prepared starting from saccharin sodium. The novel compounds were characterized using elemental analyses and different spectroscopic methods. Assessment of the antiviral activities of these novel compounds against a broad panel of viruses in different cell cultures revealed that only the thiazole derivatives belonging to the benzisothiazol‐3(2H)‐one‐1,1‐dioxide series are the active ones. All thiazole derivatives 12a–d showed activity against both varicella‐zoster virus, especially TK− VZV strain 07‐1, and the cytomegalovirus strains AD‐169 and Davis in human embryonic lung (HEL) cell culture. New benzenesulfonamide (4a–f, 5a–b, 6, 7) and 1,2‐benzisothiazol‐3(2H)‐one‐1,1‐dioxide (9a–c, 10, 12a–d) derivatives were prepared starting from saccharin sodium (1). Antiviral activity assessment revealed that benzisothiazol‐3(2H)‐one‐1,1‐dioxides bearing the thiazole moiety (12a–d) exhibited the highest activity (EC50  =  20  μM) against varicella‐zoster virus, especially TK− VZV strain 07‐1.