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 (MIC(50)=1.56 microg/mL) exhibited in vitro potent antifungal activity compared to the clinically useful antifungal drug Fluconazole (MIC(50)=2.0 microg/mL) against Sporothrix. schenckii. Compound 2a (MIC(50)=1.56 microg/mL) also exhibited same antifungal activity compared to clinically useful drug Amphotericin-B (MIC(50)=1.56 microg/mL) against Trichophyton. mentagraphytes.
Tandon
Vishnu K
VK
Department of Chemistry, University of Lucknow, Lucknow 226007, India.
Maurya
Hardesh K
HK
Tripathi
Ashutosh
A
ShivaKeshava
G B
GB
Shukla
Praveen K
PK
Srivastava
Pallavi
P
Panda
Dulal
D
D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects*; D006367:HeLa Cells; D006801:Humans; D006873:Hydroquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010640:Phenothiazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013175:Sporothrix / Q000187:drug effects; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D000970:Antineoplastic Agents; D006873:Hydroquinones; D010640:Phenothiazines; C063601:1,4-naphthohydroquinone