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Synthesis, Structure and Cytotoxic Properties of Copper(II) Complexes of 2-Iminocoumarins Bearing a 1,3,5-Triazine or Benzoxazole/Benzothiazole Moiety
- A series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h, 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b, and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c were obtained by reacting of appropriate 2-iminocoumarin ligands L1a-h, L3a-b, and L5a-c with 3-fold molar excess of copper(II) chloride. The structure of these compounds was confirmed by IR spectroscopy, elemental analysis, and single-crystal X-ray diffraction data (2f, 2g, 2h, and 6c). All the synthesized complexes were screened for their activity against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO, and RT-4 by using a crystal violet microtiter plate assay and relationships between structure and in vitro cytotoxic activity are discussed. The coordination of 2-iminocoumarins with copper(II) ions resulted in complexes 2a-h, 4a-b, and 6a-c with significant inhibitory properties toward tested tumor cell lines with IC50 values ranging from 0.04 μM to 15.66 μM. In comparison to the free ligands L1a-h, L3a-b, and L5a-c, the newly prepared Cu(II) complexes often displayed increased activity. In the series of copper(II) complexes of 2-imino-2H-chromen-3-yl-1,3,5-triazines 2a-h the most potent compound 2g contained a 4-phenylpiperazine moiety at position 6 of the 1,3,5-triazine ring and an electron-donating diethylamino group at position 7′ of the 2-iminocoumarin scaffold. Among the Cu(II) complexes of 3-(benzoxazol-2-yl)-2H-chromen-2-imines 4a-b and 3-(benzothiazol-2-yl)-2H-chromen-2-imines 6a-c the most active was benzoxazole-2-iminocoumarin 4b that also possessed a diethylamino group at position 7′ of the 2-iminocoumarin moiety. Moreover, compound 4b was found to be the most prominent agent and displayed the higher potency than cisplatin against tested cell lines.
Author: | Anna Makowska, Franciszek Sączewski, Patrick J. BednarskiORCiD, Maria Gdaniec, Łukasz Balewski, Magdalena Warmbier, Anita Kornicka |
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URN: | urn:nbn:de:gbv:9-opus-76066 |
DOI: | https://doi.org/10.3390/molecules27217155 |
ISSN: | 1420-3049 |
Parent Title (English): | Molecules |
Publisher: | MDPI |
Place of publication: | Basel |
Editor: | Mostafa A. Hussien |
Document Type: | Article |
Language: | English |
Date of first Publication: | 2022/10/22 |
Release Date: | 2022/11/14 |
Tag: | 1,3,5-triazines; 2; 2-imino-2; 2-iminocoumarins; X-ray analysis; benzothiazoles; benzoxazoles; copper(II) complexes; in vitro cytotoxic activity |
GND Keyword: | - |
Volume: | 27 |
Article Number: | 7155 |
Page Number: | 20 |
Licence (German): | Creative Commons - Namensnennung |