Synthesis, antiproliferative and antifungal activities of some 2-(2,4-dihydroxyphenyl)-4H-3,1-benzothiazines.
A new method for the synthesis of 4H-3,1-benzothiazine skeleton is described. The compounds were obtained by the reaction of sulfinylbis(2,4-dihydroxythiobenzoyl) with o-substituted anilines bearing an activated methylene group (-CH2OH, -CH2NR1R2), o-aminobenzanilides or 2-aminobenzophenones. The reaction proceeded through thiobenzanilide intermediates, which were converted to the 4H-3,1-benzothiazine fused ring by an endocyclization process. The compounds were tested for their antiproliferative properties against the cells of a human breast cancer T47D line. The activity of some compounds was comparable to that of cisplatin, studied as a control. A strong antifungal effect against the strains of moulds, yeasts and dermatophytes was also found.
Matysiak
Joanna
J
Department of Chemistry, Agricultural University, Akademicka 15, 20-950 Lublin, Poland. matysiak@ar.lublin.pl
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D052160:Benzothiazoles; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D003500:Cyclization; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D014961:X-Ray Diffraction
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D052160:Benzothiazoles; D013844:Thiazoles; C005465:benzothiazole