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Amidine-aminoisoquinoline substitution

By Wavefunction on Friday, June 22, 2007
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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
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4 comments:

  1. Russ12:55 PM, June 22, 2007

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

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  2. Wavefunction1:01 PM, June 22, 2007

    Corrected, thanks

    ReplyDelete
  3. Georg-Martin Krapper2:14 PM, June 25, 2007

    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.

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  4. Wavefunction2:55 PM, June 25, 2007

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

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