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  • Authors: Nam, Tae-gyu (2006)

  • Pyridinol and pyrimidinol analogs of acetaminophen were synthesized as they have modified electronic properties without a significant structural modification. It was observed that inhibition of prostaglandin H2 synthases (PGHSs), or cyclooxygenases (COXs) by acetaminophen and the analogs is dependent on their abilities to donate a hydrogen atom or electron to the oxidized PGHS peroxidase heme. These abilities are reflected in their bond dissociation enthalpies (BDEs) and ionization potentials (IPs). Inhibitory activities of the analogs increased in the higher pH medium where the ionized form of the analogs are predominant, supporting that electron transfer from the analogs to peroxidase heme would be the major contributor to the mechanism of inhibition. Pyridinol and pyrimidinol an...