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Molecules 2018, 23(11), 2902; https://doi.org/10.3390/molecules23112902

Synthesis of Jacaranone-Derived Nitrogenous Cyclohexadienones and Their Antiproliferative and Antiprotozoal Activities

1
Institute of Pharmaceutical Sciences, Pharmaceutical Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, Austria
2
Institute of Pharmaceutical Sciences, Pharmacognosy, University of Graz, Universitaetsplatz 4, 8010 Graz, Austria
3
Institute for Chemistry and Technology of Materials (ICTM), Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria
4
Swiss Tropical and Public Health Institute, Socinstrasse 57, 4002 Basel, Switzerland
5
University of Basel, Petersplatz 1, 4003 Basel, Switzerland
*
Author to whom correspondence should be addressed.
Academic Editors: Claudio Santi and Luca Sancineto
Received: 26 September 2018 / Revised: 19 October 2018 / Accepted: 29 October 2018 / Published: 7 November 2018
(This article belongs to the Special Issue Chemistry & Health)
Full-Text   |   PDF [4477 KB, uploaded 7 November 2018]   |  

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. View Full-Text
Keywords: antiproliferative activity; antiprotozoal activity; green chemistry; natural products; jacaranone antiproliferative activity; antiprotozoal activity; green chemistry; natural products; jacaranone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Presser, A.; Lainer, G.; Kretschmer, N.; Schuehly, W.; Saf, R.; Kaiser, M.; Kalt, M.-M. Synthesis of Jacaranone-Derived Nitrogenous Cyclohexadienones and Their Antiproliferative and Antiprotozoal Activities. Molecules 2018, 23, 2902.

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