An Efficient Parallel Synthesis of Capsazepine and Capsazepine Analogs

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

Journal Name: Combinatorial Chemistry & High Throughput Screening
Accelerated Technologies for Biotechnology, Bioassays, Medicinal Chemistry and Natural Products Research

Volume 7 , Issue 2 , 2004

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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.

Keywords: vanilloid receptor (VR1), tetralone, benzazepine

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Article Details

Year: 2004
Page: [153 - 161]
Pages: 9
DOI: 10.2174/138620704773120838
Price: $65

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