Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors
BIOORGANIC CHEMISTRY, cilt.90, 2019 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 90
- Basım Tarihi: 2019
- Doi Numarası: 10.1016/j.bioorg.2019.103095
- Dergi Adı: BIOORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Anahtar Kelimeler: Mannich bases, Chalcone, Phenol, Carbonic anhydrase, Cytotoxicity, ERYTHROCYTE ISOZYMES I, CYTOTOXIC ACTIVITIES, HCA I, CORRESPONDING PIPERIDINOLS, ANTIMICROBIAL EVALUATION, THERAPEUTIC APPLICATIONS, ACETYLCHOLINE ESTERASE, ANGELICA-KEISKEI, 1ST SYNTHESIS, DERIVATIVES
- Atatürk Üniversitesi Adresli: Evet
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.