Synthesis and biological screening of some novel amidocarbamate derivatives of ketoprofen.
A series of novel ketoprofen derivatives 4a-j bearing both amide and carbamate functionalities were prepared using benzotriazole. Selective reduction of ketoprofen produced hydroxy derivative 2, which reacts with one or 2 mol of 1-benzotriazole carboxylic acid chloride (1) gave benzotriazole derivatives 3a and 3b respectively. Antioxidative screenings revealed that the prepared compounds 3b and 4a-j possess excellent lipid peroxidation inhibition at 0.1 mM concentration. Two of the compounds 3b and 4 g also showed high soybean lipoxygenase inhibition activity, where as the amidocarbamate derivatives of ketoprofen showed only weak reducing activity against 1,1-diphenyl-2-picrylhydrazyl radicals. No selective antiviral effects were noted for the tested compounds against a broad variety of DNA and RNA viruses.
Sahoo
Prasanta Kumar
PK
Sri Vasavi Institute of Pharmaceutical Sciences, Pedatadepalli, Tadepalligudem, West Godavari District 534101, Andhra Pradesh, India. psahoo.phar@gmail.com
Behera
Pritishova
P
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000737:chemistry; D002219:Carbamates / Q000737:chemistry*; D002460:Cell Line; D054697:Cytostatic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D004267:DNA Viruses / Q000187:drug effects; D004353:Drug Evaluation, Preclinical; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D019787:Linoleic Acid / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008084:Lipoxygenase / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D010851:Picrates / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012328:RNA Viruses / Q000187:drug effects; D013025:Glycine max / Q000201:enzymology
D000998:Antiviral Agents; D001713:Biphenyl Compounds; D002219:Carbamates; D054697:Cytostatic Agents; D016166:Free Radical Scavengers; D016859:Lipoxygenase Inhibitors; D010851:Picrates; D015363:Quinolones; D019787:Linoleic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D008084:Lipoxygenase