Field of Science

Amidine-aminoisoquinoline substitution

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Nice replacement to preserve overall electronic characteristics such as HBonding, but increase absorbtion and lipophilicity, and decrease basicity. From a nice review on FactorXa inhibitor development from Structure-Based Drug Discovery


  1. You might have one too many nitrogens in that first structure...

  2. It's a bit misleading to draw the structure as neutral because it's most likely to bind as a cation. The lower pKa of the aminoisoquinoline will ensure that there is plenty of neutral form to get thru membranes. I commented on a 5/7/2007 post on aromaticity in carbon-based curiosities and mentioned pKa of isoquinolines. From what I remember an amino group in the 6-position will also push the pKa to approximately 7.

  3. Thanks...took care of it. DMAP is ~9 I believe?


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