Synthesis of O-prenylated and O-geranylated derivatives of 5-benzylidene2,4-thiazolidinediones and evaluation of their free radical scavenging activity as well as effect on some phase II antioxidant/detoxifying enzymes.
A series of 5-arylidene-2,4-thiazolidinediones and its geranyloxy or prenyloxy derivative were synthesized and studied for their radical scavenging activity using 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Their comparable scavenging activities were expressed as IC50 value. Compounds 2c, 2d, 4d, and 6a showed appreciable radical scavenging activities. The vanillin based thiazolidinedione compound 2c displayed highest activity comparable to that of alpha-tocopherol. But in vivo, compound 6a showed better results in inducing phase II detoxifying/antioxidative enzyme.
Hossain
Sk Ugir
SU
Department of Cancer Chemoprevention, Chittaranjan National Cancer Institute, 37, S.P. Mukherjee Road, Kolkata 700 026, West Bengal, India.
Bhattacharya
Sudin
S
D000975:Antioxidants; D001547:Benzaldehydes; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers / Q000138:chemical synthesis* / Q000737:chemistry; D020128:Inhibitory Concentration 50; D010851:Picrates; D017368:Protein Prenylation; D013329:Structure-Activity Relationship; D045162:Thiazolidinediones / Q000138:chemical synthesis* / Q000737:chemistry; D024502:alpha-Tocopherol
D000975:Antioxidants; D001547:Benzaldehydes; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D010851:Picrates; D045162:Thiazolidinediones; C100058:vanillin; C004931:1,1-diphenyl-2-picrylhydrazyl; D024502:alpha-Tocopherol