Synthesis and Investigations of Building Blocks with Dibenzo[<i>b</i>,<i>f</i>] Oxepine for Use in Photopharmacology

Abstract

The synthesis of photoswitchable azo-dibenzo[b,f]oxepine derivatives and microtubule inhibitors were described. Subsequently, we examined the reaction of methoxy derivative 3-nitrodibenzo[b,f]oxepine with different aldehydes and in the presence of BF3·OEt2 as a catalyst. Our study provided a very concise method for the construction of the azo-dibenzo[b,f]oxepine skeleton. The analysis of products was run using experimental and theoretical methods. Next, we evaluated the E/Z isomerization of azo-dibenzo[b,f]oxepine derivatives, which could be photochemically controlled using visible-wavelength light.

Keywords

• <i>azo</i>-dibenzo[<i>b</i>,<i>f</i>]oxepine derivatives
• photoisomerisation
• tubulin inhibitor