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Medicinal Chemistry Research

, Volume 28, Issue 10, pp 1694–1703 | Cite as

New pyranoquinoline derivatives as vascular-disrupting anticancer agents

  • Florian Schmitt
  • Rainer Schobert
  • Bernhard BiersackEmail author
Original Research
  • 39 Downloads

Abstract

A series of new 4-aryl-pyranoquinoline derivatives with a focus on meta-nitro and meta-halophenyl derivatives were prepared and investigated for their structure-dependent antiproliferative effects on a panel of six human cancer cell lines. The compounds were highly active with nanomolar IC50 values. Some of them even exceeded the activities of known analogs such as LY290181 in vitro while not affecting non-malignant fibroblasts. These most active derivatives led to an increase of reactive oxygen species in cancer cells and to a disruption of their microtubular cytoskeleton by inhibiting tubulin polymerization. They also displayed vascular-disrupting activity in ovo as assessed by chorioallantoic membrane assays.

Keywords

Pyranoquinoline Anticancer agents Tubulin polymerization inhibitors Vascular-disrupting agents 

Notes

Acknowledgements

We thank Madeleine Gold and Kerstin Hannemann (Organic Chemistry 1, University of Bayreuth) for technical assistance.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

44_2019_2406_MOESM1_ESM.docx (17.6 mb)
Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Organic Chemistry LaboratoryUniversity of BayreuthBayreuthGermany

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