This contribution presents an historical account of the medicinal chemistry of the DATA (diaryltriazine) and DAPY (diarylpyrimidine) series of inhibitors of HIV-1 reverse transcriptase (NNRTIs). The history extends over a period of more than 18 years, starting from 1987, and is still ongoing. The authors attempt to describe the often tortuous and unpredictable route that led from the virological screening of compounds, over serendipitous chemistry, X-ray crystallography, molecular modelling, animal pharmacokinetics, biochemistry and physical chemistry to the design and further development of highly potent anti-HIV compounds, three of which are now in advanced stages of clinical studies. The emphasis in this historical account is on the medicinal chemistry that led to the DATA and DAPY series of NNRTIs.
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