Constrained TRPV1 agonists synthesized via silver-mediated intramolecular azo-methine ylide cycloaddition of α-iminoamides

TO Painter, K Kaszas, J Gross, JT Douglas…

Index: Painter, Thomas O.; Kaszas, Krisztian; Gross, Jacklyn; Douglas, Justin T.; Day, Victor W.; Iadarola, Michael J.; Santini, Conrad Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 3 p. 963 - 968

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Abstract

Abstract As part of an effort to identify agonists of TRPV1, a peripheral sensory nerve ion channel, high throughput screening of the NIH Small Molecule Repository (SMR) collection identified MLS002174161, a pentacyclic benzodiazepine. A synthesis effort was initiated that ultimately afforded racemic seco analogs 12 of the SMR compound via a silver mediated intramolecular [3+ 2] cycloaddition of an azo-methine ylide generated from α- ...

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