Synthesis and biological evaluation of some new mono Mannich bases with piperazines as possible anticancer agents and carbonic anhydrase inhibitors |
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| Institution: | 1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey;2. Division of Biochemistry, Meikai University School of Dentistry, Sakado, Saitama, Japan;3. Meikai University Research Institute of Odontology (M-RIO), Meikai University School of Dentistry, Sakado, Saitama, Japan;4. Faculty of Science, Department of Chemistry, Ataturk University, Erzurum, Turkey;5. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Anadolu University, Eski?ehir, Turkey;6. Neurofarba Department, Sezione di Scienza Farmaceutiche e Nutraceutiche, Universita egli Studi di Firenze, Via U. Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;1. University of Florence, Department of Neuroscience, Psychology, Drug Research and Child''s Health, Section of Pharmaceutical and Nutraceutical Sciences, Via Ugo Schiff 6, 50019, Sesto Fiorentino, Italy;2. University of Florence, Department of Chemistry, via della Lastruccia, 50019, Sesto Fiorentino, Italy;3. University of Florence, Department NEUROFARBA – Pharmaceutical and Nutraceutical section; Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Firenze, via Ugo Schiff 6, I-50019, Sesto Fiorentino, Firenze, Italy;4. University of Florence, Department of Neuroscience, Psychology, Drug Research and Child''s Health, Section of Pharmacology and Toxicology, Viale Gaetano Pieraccini 6, 50100, Florence, Italy;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, Erzurum, Turkey;2. Department of Biochemistry, Faculty of Pharmacy, Ege University, Bornova, Izmir, Turkey;3. Department of Physiology, Faculty of Medicine, Ataturk University, Erzurum, Turkey;4. Neurofarba Department, Sezione di Scienze Farmaceutiche e Nutraceutiche, Università degli Studi di Firenze, Via U. Schiff 6, 50019 Sesto Fiorentino (Florence), Italy;1. Sakarya University, Faculty of Science and Arts, Department of Chemistry, 54187 Serdivan Sakarya, Turkey;2. Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey;3. Sakarya University, Faculty of Medicine, Infectious Diseases and Clinical Microbiology Department, 54290 Adapazar? Sakarya, Turkey;1. Department of Chemistry, Jamanaben Narottambhai Motiram Patel Science College, Bharthana (Vesu), Surat 395017, Gujarat, India;2. Department of Chemistry, Veer Narmad South Gujarat University, Udhana-Magdalla Road, Surat 395007, Gujarat, India;3. Departamento de Microbiología Ambiental y Biotecnología, Universidad Autónoma de Campeche, Av. Agustín Melgar, s/n, Campeche, 24039, Mexico;4. Laboratorio de Biotecnologia Farmaceutica, Centro de Biotecnología Genómica, Instituto Politécnico Nacional, Reynosa, 88710, Mexico;1. School of Chemistry, The University of New South Wales, Sydney, NSW 2052, Australia;2. Children’s Cancer Institute Australia, Lowy Cancer Research Centre, UNSW, Randwick, NSW, Australia;3. Australian Centre for NanoMedicine, University of New South Wales, Sydney, NSW 2052, Australia;4. Metronomics Global Health Initiative, Marseille, France |
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| Abstract: | 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 1H NMR, 13C 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. |
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| Keywords: | Mannich bases Chalcone Phenol Carbonic anhydrase Cytotoxicity |
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