Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors.
We have synthesised a series of 2-[[2-alkoxy-6-pentadecylphenyl)methyl]thio]-1H-benzimidazoles/benzothiazoles and benzoxazoles from anacardic acid and investigated their ability to inhibit human cyclooxygenase-2 enzyme (COX-2). The active compounds were screened for cyclooxygenase-1 (COX-1) inhibition. Compound 13 is 384-fold and 19 is more than 470-fold selective towards COX-2 compared to COX-1. Thus, this class of compounds may serve as excellent candidates for selective COX-2 inhibition.
Paramashivappa
R
R
Vittal Mallya Scientific Research Foundation, PO Box #406, K. R. Road, Bangalore 560 004, India.
Phani Kumar
P
P
Subba Rao
P V
PV
Srinivasa Rao
A
A
D001562:Benzimidazoles / Q000138:chemical synthesis / Q000494:pharmacology; D052160:Benzothiazoles; D001583:Benzoxazoles / Q000138:chemical synthesis / Q000494:pharmacology; D001769:Blood / Q000378:metabolism; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D008565:Membrane Proteins; D011451:Prostaglandin-Endoperoxide Synthases; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis / Q000494:pharmacology
D001562:Benzimidazoles; D052160:Benzothiazoles; D001583:Benzoxazoles; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D006571:Heterocyclic Compounds; D007527:Isoenzymes; D008565:Membrane Proteins; D013844:Thiazoles; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; C496511:PTGS1 protein, human; C496540:PTGS2 protein, human; D011451:Prostaglandin-Endoperoxide Synthases; C005465:benzothiazole