Synthesis of jacaranone-derived nitrogenous cyclohexadienones and their antiproliferative and antiprotozoal activities

Armin Presser*, Gunda Lainer, Nadine Kretschmer, Wolfgang Schuehly, Robert Saf, Marcel Kaiser, Marc Manuel Kalt

*Korrespondierende/r Autor/in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikel

Abstract

The cytotoxic and antiprotozoal activities of the phytoquinoide, jacaranone, and related compounds have been an ongoing topic in recent drug discovery. Starting from the natural product-derived cyclohexadienone scaffold, a series of nitrogen-containing derivatives were synthesized and subsequently evaluated for their antiproliferative and antiprotozoal activity. Anticancer potency was analyzed using different types of cancer cell lines: MDA-MB-231 breast cancer, CCRF-CEM leukemia, HCT-116 colon cancer, U251 glioblastoma, and, in addition, non-tumorigenic MRC-5 lung fibroblasts. Antiproliferative activities at micromolar concentrations could be shown. Antiprotozoal activity was assessed against Plasmodium falciparum NF54 and Trypanosoma brucei rhodesiense STIB900. For all compounds, selectivity indices (SI) were calculated based on assessed cytotoxicity towards L6 cells. In addition, the structure-activity-relationships and physicochemical parameters of these compounds are discussed.

Originalspracheenglisch
Aufsatznummer2902
FachzeitschriftMolecules
Jahrgang23
Ausgabenummer11
DOIs
PublikationsstatusVeröffentlicht - 7 Nov 2018

ASJC Scopus subject areas

  • Analytische Chemie
  • !!Chemistry (miscellaneous)
  • !!Molecular Medicine
  • !!Pharmaceutical Science
  • !!Drug Discovery
  • !!Physical and Theoretical Chemistry
  • Organische Chemie

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