Synthesis and Evaluation of 2-Pyridinone Derivatives as Specific HIV-1 Reverse Transcriptase Inhibitors. 3. Pyridyl and Phenyl Analogs of 3-Aminopyridin-2(1H)-one

John S. Wai, Theresa M. Williams, Dona L. Bamberger, Thorsten E. Fisher, Jacob M. Hoffman, Ronald J. Hudcosky, Suzanne C. MacTough, Clarence S. Rooney, Walfred S. Saari, Craig M. Thomas, Mark E. Goldman, Julie A. O'Brien, Emilio A. Emini, Jack H. Nunberg, Julio C. Quintero, William A. Schleif, Paul S. Anderson

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Abstract

In an ongoing effort to develop novel nonnucleoside, specific human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) inhibitors, a series of 3-[(pyridylmethyl)amino]- and 3-[(phenylmethyl)amino]-2-pyridinone derivatives was synthesized and tested for HIV-1 RT inhibitory activity. The more potent compounds have a 2′-methoxy group and 4′- and/or 5′-aliphatic substituents on the pyridyl and phenyl rings. Several of the more potent compounds were also evaluated for antiviral activity in MT-4 cell culture. From this series of compounds, 3-[N-[(5-ethyl-2-methoxy-6-methyl-3-pyridyl)methyl]amino]-5-ethyl-6-methylpyridin-2(1H)-one (6) was selected for clinical evaluation.

Original languageEnglish
Pages (from-to)249-255
Number of pages7
JournalJournal of Medicinal Chemistry
Volume36
Issue number2
DOIs
StatePublished - 1993

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