An Efficient Parallel Synthesis of Capsazepine and Capsazepine Analogs

Title: An Efficient Parallel Synthesis of Capsazepine and Capsazepine Analogs

Volume: 7 Issue: 2

Author(s): Laykea Tafesse and Donald J. Kyle

Affiliation:

Keywords: vanilloid receptor (VR1), tetralone, benzazepine

Abstract: Capsazepine (CPZ, 1) is a well-known vanilloid receptor (VR1) antagonist that has been cited widely used inthe literature. However the current synthetic methods used for the total synthesis of CPZ are lengthy, involve multiple purification steps, and produce low yields. Here we describe a new and highly efficient synthesis of benzazepine 3, a synthetic precursor of CPZ, in only two steps and 59% overall yield from a commercially available tetralone 2 via a Schmidt reaction as a key step. Moreover, we apply parallel synthesis techniques to prepare CPZ and CPZ analogs. Our approach enables the possibility of preparing larger, and more diverse libraries of CPZ analogs.

Cite this article as:

Tafesse Laykea and Kyle J. Donald, An Efficient Parallel Synthesis of Capsazepine and Capsazepine Analogs, Combinatorial Chemistry & High Throughput Screening 2004; 7 (2) . https://dx.doi.org/10.2174/138620704773120838