2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and Biological evaluation as potential antiproliferative and antifungal agents

A series of 2-chloro-3-arylsulfanyl-[1,4]naphthoquinones (2), 2,3-bis-arylsulfanyl-[1,4]naphthoquinones (3) and 12H-benzo[b]phenothiazine-6,11-diones and their analogs 6–8 were synthesized and evaluated for their antiproliferative activity against human cervical cancer (HeLa) cells. Compounds 3a and 3b were found to possess most potent antiproliferative and cell killing ability. Compounds 1–8 were also evaluated for antifungal activities. The structure–activity relationship of these compounds was studied and the results show that compound 2a (MIC50 = 1.56 μg/mL) exhibited in vitro potent antifungal activity compared to the clinically useful antifungal drug Fluconazole (MIC50 = 2.0 μg/mL) against Sporothrix. schenckii. Compound 2a (MIC50 = 1.56 μg/mL) also exhibited same antifungal activity compared to clinically useful drug Amphotericin-B (MIC50 = 1.56 μg/mL) against Trichophyton. mentagraphytes.

The synthesis, antiproliferative and antifungal activities of 1–8 are described.Figure optionsDownload as PowerPoint slide