2012
DOI: 10.1111/j.1747-0285.2012.01372.x
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A Combined Study Using Ligand‐Based Design, Synthesis, and Pharmacological Evaluation of Analogues of the Acetaminophen Ortho‐Regioisomer with Potent Analgesic Activity

Abstract: A ligand-based drug design study was performed to acetaminophen regioisomers as analgesic candidates employing quantum chemical calculations at the DFT ⁄ B3LYP level of theory and the 6-31G* basis set. To do so, many molecular descriptors were used such as highest occupied molecular orbital, ionization potential, H-O bond dissociation energies, and spin densities, which might be related to quench reactivity of the tyrosyl radical to give N-acetyl-p-benzosemiquinone-imine through an initial electron withdrawing… Show more

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Cited by 5 publications
(2 citation statements)
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“…In the same way, EWGs (-F, -Cl, and -NO 2 ) increased BDE NH values for 91.52 (7), 91.69 (8), and 92.81 kcal/mol (9). These results show that all regioisomers would be less toxic than acetaminophen [21].…”
Section: Design Of Acetaminophen Regioisomersmentioning
confidence: 69%
“…In the same way, EWGs (-F, -Cl, and -NO 2 ) increased BDE NH values for 91.52 (7), 91.69 (8), and 92.81 kcal/mol (9). These results show that all regioisomers would be less toxic than acetaminophen [21].…”
Section: Design Of Acetaminophen Regioisomersmentioning
confidence: 69%
“…As a consequence, research on new APAP derivatives is an active area of drug development [15][16][17][18][19][20][21][22][23][24][25][26]. According to current reports, a structural modification of the N-acetylp-aminophenol skeleton can improve, reduce, or even change the enzymatic activities of a drug and, thus, the pharmacological properties including cytotoxicity.…”
Section: Introductionmentioning
confidence: 99%