Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors
Özet
New mono Mannich bases, (2-(4-hydroxy-3-((4-substituephenylpiperazin-1-yl)methyl)benzylidene)-2,3-dihydro-1H-inden-1-one), were prepared to evaluate their cytotoxic/anticancer properties and also their inhibitory effects on human carbonic anhydrase I and II isoenzymes (hCA I and II). Amine part was changed as [N-phenylpiperazine (1),N-benzylpiperazine (2), 1-(2-fluorophenyl)piperazine (3), 1-(4-fluorophenyl)piperazine (4), 1-(2-methoxyphenyl)piperazine (5)]. The structure of the synthesized compounds was characterized by H-1 NMR, C-13 NMR and HRMS spectra. Cytotoxicity results of the series pointed out that the compound 4 had the highest tumor selectivity value (TS: 59.4) possibly by inducing necrotic cell death in series. Additionally, all compounds synthesized showed a good inhibition profile towards hCA I and II isoenzymes with the Ki values between 29.6 and 58.4 nM and 38.1-69.7 nM, respectively. These values were lower than the reference compound AZA. However, it seems that the compounds 4 and 2 can be considered as lead compounds of CA studies with the lowest Ki values in series for further designs.
Anahtar kelimeler
Atıf için künye
TUĞRAK, M., Gül, H. İ., BANDOW, K., Sakagami, H., Gülçin, İ., Ozkay, Y., & Supuran, C. T. (2019). Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors. Bioorganic Chemistry, 90. https://doi.org/10.1016/j.bioorg.2019.103095
BibTeX
@article{tugrak2019-19987,
author = {TUĞRAK, Mehtap and Gül, Halise İnci and BANDOW, Kenjiro and Sakagami, Hiroshi and Gülçin, İlhami and Ozkay, Yusuf and Supuran, Claudiu T.},
title = {Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors},
journal = {Bioorganic Chemistry},
year = {2019},
volume = {90},
issn = {0045-2068},
doi = {10.1016/j.bioorg.2019.103095},
url = {https://akademik.atauni.edu.tr/yayinlar/19987-synthesis-and-biological-evaluation-of-some-new-mono-mannich-bases-with}
}