Synthesis and Study of Building Blocks with Dibenzo[ b,f]oxepine: Potential Microtubule Inhibitors

Piotr Tobiasz; Filip Borys; Marta Kucharska; Marcin Poterała; Hanna Krawczyk

doi:10.3390/ijms25116155

Synthesis and Study of Building Blocks with Dibenzo[ b,f]oxepine: Potential Microtubule Inhibitors

Int J Mol Sci. 2024 Jun 3;25(11):6155. doi: 10.3390/ijms25116155.

Authors

Piotr Tobiasz¹, Filip Borys^{1

2}, Marta Kucharska¹, Marcin Poterała¹, Hanna Krawczyk¹

Affiliations

¹ Department of Organic Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
² Nencki Institute of Experimental Biology, Polish Academy of Sciences, 3 Pasteur Street, 02-093 Warsaw, Poland.

Abstract

The synthesis of biphenylmethoxydibenzo[b,f]oxepine or photoswitchable fluorinated dibenzo[b,f]oxepine derivatives with one or three azo bonds, potential microtubule inhibitors, is described. Our studies provide a concise method for constructing derivatives containing the dibenzo[b,f]oxepine skeleton. An 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: azo-dibenzo[b,f]oxepine derivative; biological activity; photoisomerization; tubulin inhibitor.

MeSH terms

Microtubules / drug effects
Microtubules / metabolism
Molecular Structure
Tubulin Modulators* / chemical synthesis
Tubulin Modulators* / chemistry
Tubulin Modulators* / pharmacology

Substances

Tubulin Modulators

Grants and funding

This research was funded by the Warsaw University of Technology within the Excellence Initiative: Research University (IDUB) program (Nchem5). This work was implemented as a part of Operational Project Knowledge Education Development 2014–2020 co-financed by the European Social Fund (Project No. POWR.03.02.00-00-I007/16-00 (POWER 2014–2020)) and by the Diamond Grant project (the scientific work financed from budget funds for science in the years 2019–2023).