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Medicinal Chemistry Research

, Volume 14, Issue 5, pp 241–259 | Cite as

Biososteric Replacement in the Design and Synthesis of Ligands for Nicotinic Acetylcholine Receptors

  • Weilin Sun
  • Michael P. Blanton
  • Jerome L. Gabriel
  • Daniel J. CanneyEmail author
Article

A series of ethers containing pyrrolidine and/or pyridine bioisosteres was synthesized and evaluated as nicotinic ligands. The dimethylaminoethoxypridines 6 and 7 inhibited the specific bind of (-)-[3H]Nicotine with Ki values of 300 nM and 450 nM, respectively. Compounds 8 and 9 were found to have Ki values of 3390 nM and 360 nM. These results suggest that dialkylamino and appropriately substituted benzene rings (NO2, 8; OH, 9) are bioisosteric replacements for pyrrolidine and pyridine, respectively.

Keywords

Ether Benzene Nicotine Pyridine Acetylcholine 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Birkhäuser 2006

Authors and Affiliations

  • Weilin Sun
    • 1
  • Michael P. Blanton
    • 2
  • Jerome L. Gabriel
    • 3
  • Daniel J. Canney
    • 1
    Email author
  1. 1.Department of Pharmaceutical SciencesTemple University, School of PharmacyPhiladelphiaUSA
  2. 2.Department of BiochemistryTemple University, School of MedicinePhiladelphiaUSA
  3. 3.Department of Pharmacology and NeuroscienceTexas Tech University HSCLubbockUSA

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