Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzimidazoles / chemical synthesis
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Benzimidazoles / pharmacology
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Benzothiazoles
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Benzoxazoles / chemical synthesis
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Benzoxazoles / pharmacology
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Blood / metabolism
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Cyclooxygenase 1
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Cyclooxygenase 2
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors / chemical synthesis*
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Cyclooxygenase Inhibitors / pharmacology
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Drug Evaluation, Preclinical
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Heterocyclic Compounds / chemical synthesis*
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Heterocyclic Compounds / pharmacology*
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Humans
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Inhibitory Concentration 50
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Isoenzymes / antagonists & inhibitors
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Membrane Proteins
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Prostaglandin-Endoperoxide Synthases
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Structure-Activity Relationship
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Thiazoles / chemical synthesis
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Thiazoles / pharmacology
Substances
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Benzimidazoles
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Benzothiazoles
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Benzoxazoles
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Cyclooxygenase 2 Inhibitors
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Cyclooxygenase Inhibitors
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Heterocyclic Compounds
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Isoenzymes
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Membrane Proteins
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Thiazoles
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Cyclooxygenase 1
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Cyclooxygenase 2
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PTGS1 protein, human
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PTGS2 protein, human
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Prostaglandin-Endoperoxide Synthases
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benzothiazole