3-(2,5-Dihydro-1H-pyrrol-2-ylmethoxy)pyridines: synthesis and analgesic activity.

Bioorg Med Chem Lett

Syntagon AB, Tallvägen 2, Box 2073, SE-15102 Södertälje, Sweden.

Published: March 2005

AI Article Synopsis

  • The researchers describe a method to create ethers of specific pyrroline compounds using a process that includes the formation of a cyclic sulfamidate.
  • The study involved synthesizing new versions of two known compounds, epibatidine and tebanicline.
  • The new compounds were then tested for their ability to alleviate pain using a mouse formalin model.

Article Abstract

We disclose an efficient procedure for the preparation of ethers of 2-substituted 2-hydroxymethylpyrroline and of 2-aminomethyl-3-pyrrolines, involving, as a key step, formation and nucleophilic ring opening of a cyclic sulfamidate. Several new analogs of epibatidine (1) and tebanicline (ABT-594, 2) were prepared and tested for analgesic activity in the mouse formalin model.

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http://dx.doi.org/10.1016/j.bmcl.2005.01.058DOI Listing

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