Synthesis and biological activity of substituted 3-fluoro/3-trifluoromethyl 10 H-phenothiazines, its ribofuranosides and sulfones

• Published in: Journal of fluorine chemistry Vol. 132; no. 6; pp. 420 - 426
• Main Authors: Gautam, Naveen, Goyal, Kshamta, Saini, Omprakash, Kumar, Ashok, Gautam, D.C.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 2011
• Subjects: Antimicrobial activities; Antioxidant activities; Ribofuranosides; Smiles rearrangement; Sulfones; Smiles rearrangement; Antioxidant activities; Antimicrobial activities; Ribofuranosides; Sulfones
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2011.04.012

The present work reveals the synthesis of substituted 3-fluoro/3-trifluoromethyl-10 H-phenothiazines, its ribofuranosides and sulfones and their characterization. The compounds were evaluated for their antioxidant and antimicrobial activities. [Display omitted] ► Synthesized compounds showed mixed radical scavenging activity in DPPH and ABTS + assay. ► These compounds showed good chemopreventive and antigenotoxic effect. ► Synthesized compounds exhibited significant antibacterial and antifungal activities. The present article describes the synthesis of new fluorinated 10H-phenothiazines by Smiles rearrangement. The reaction of these synthesized phenothiazines with sugar (beta- d-ribofuranose 1-acetate-2,3,5-tribenzoate) afforded the new ribofuranosides and the oxidation of these synthesized phenothiazines with 30% hydrogen peroxide in glacial acetic acid resulted in the formation of 10 H-phenothiazine sulfones. These compounds were evaluated for their antioxidant and antimicrobial activities (using broth microdilution method). The structural assignments of the synthesized compounds were made on the basis of elemental analysis and spectroscopic data.