Christopher Lipinski - pKa, Log P and MedChem CLOGP Fragment Values of Acidic Heterocyclic Potential Bioisosteres

Document created by Christopher Lipinski on Aug 22, 2014
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  Publication Details (including relevant citation   information): Lipinski, Christopher A., Fiese, Eugene   F., Korst, Robert J., Quantitative Structure-Activity   Relationships, 1991, 10 (2), pp   109-117

  Abstract: Log P values have been measured for   twenty phenyl and benzyl five membered heterocycles and alicyclic   analogs that might function as acidic bioisosteres. pKa's have   been measured by potentiometric titration in water and 1:1   dioxane-water. From this experimental data, twelve missing   fragmental CLOGP values are derived for use in calculating Log P   values according to the Pomona College MedChem program. Log P   values of some of the simple benzyl and phenyl heterocycles are   compared to those measured for four clinically used drugs   containing the same acidic moieties. Sulfonyl urea and acyl   sulfonamide moieties have similar pKa and Log P values suggesting   that these groups might be explored as bioisosteres.

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