New phenolic Mannich bases with piperazines and their bioactivities
Özet
In this study, new Mannich bases, 2-(4-hydroxy-3-methoxy-5-((substitutedpiperazin-1-yl)methyl)benzylidene)-2,3-dihydro-1H-inden-1-one (1, 2, 4, 5, 8), 2-(3-((substituted)piperazin-1-yl)methyl)-4-hydroxy-5-methoxybenzylidene)-2,3-dihydro-1H-inden-1-one (3, 6, 7) were synthesized with the reaction of vanilin derived chalcone compound (2-(4-hydroxy-3-methoxybenzylidene)indan-1-one), paraformaldehyde and suitable amine in 1:1.2:1 mol ratios. Amine part was changed as N-methylpiperazine (1), N-phenylpiperazine (2), N-benzyl-piperazine (3), 1-(2-methoxyphenyl)piperazine (4), 1-(3-methoxyphenyl)piperazine (5), 1-(2-fluorophenyl)piperazine (6), 1-(4-fluorophenyl)piperazine (7), and 1-(3-trifluoromethyl)phenyl piperazine (8). Compounds were evaluated in terms of cytotoxic/anticancer and CA inhibitory effects. According to the results obtained, the compounds 2 and 8 had the highest potency selectivity expression (PSE) values (60.6 and 19.2, respectively). On the other hand, the compounds 3 (Ki = 209.6 +/- 70.2 pM) and 5 (Ki = 342.66 +/- 63.72 pM) had the lowest Ki values in CA inhibition experiments towards hCA I and hCA II, respectively.
Anahtar kelimeler
Atıf için künye
Gül, H. İ., TUĞRAK, M., Gül, M., MAZLUMOĞLU, S., Sakagami, H., Gülçin, İ., & Supuran, C. T. (2019). New phenolic Mannich bases with piperazines and their bioactivities. Bioorganic Chemistry, 90. https://doi.org/10.1016/j.bioorg.2019.103057
BibTeX
@article{gul2019-19937,
author = {Gül, Halise İnci and TUĞRAK, Mehtap and Gül, Mustafa and MAZLUMOĞLU, Sertac and Sakagami, Hiroshi and Gülçin, İlhami and Supuran, Claudiu T.},
title = {New phenolic Mannich bases with piperazines and their bioactivities},
journal = {Bioorganic Chemistry},
year = {2019},
volume = {90},
issn = {0045-2068},
doi = {10.1016/j.bioorg.2019.103057},
url = {https://akademik.atauni.edu.tr/yayinlar/19937-new-phenolic-mannich-bases-with-piperazines-and-their-bioactivities}
}