Synthesis,Biological Activity Evaluation and Molecular Docking of Imidazole Derivatives Possessing Hydrazone Moiety |
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Authors: | Hüseyin Kekeçmuhammed Michael Tapera Ekrem Aydoğdu Emin Sarıpınar Elanur Aydin Karatas Eda Mehtap Uc Mesut Akyuz Burak Tüzün İlhami Gulcin Rıfat Emin Bora İlhan Özer İlhan |
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Affiliation: | 1. Department of Chemistry, Faculty of Science, Erciyes University, 38039 Kayseri, Turkey;2. Department of Molecular Biology and Genetics, Faculty of Science, Erzurum Technical University, 25050- Erzurum, Turkey;3. Atatürk University, Faculty of Science, Department of Chemistry, 25240- Erzurum, Turkey;4. Plant and Animal Production Department, Technical Sciences Vocational School of Sivas, Sivas Cumhuriyet University, 58140- Sivas, Turkey |
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Abstract: | In an attempt to identify potential active anticancer agents with low cytotoxic properties and CA inhibitors, a new series of hybrid compounds incorporating imidazole ring and hydrazone moiety as part of their structure were synthesized by aza-Michael addition reaction followed by intramolecular cyclization. The structure of synthesized compounds was elucidated using various spectral techniques. Synthesized compounds were evaluated for their in vitro anticancer (prostate cell lines; PC3) and CA inhibitory (hCA I and hCA II) activity. Among them, some compound displayed remarkable anticancer activity and CA inhibitory activity with Ki values in range of 17.53±7.19–150.50±68.87 nM against cytosolic hCA I isoform associated with epilepsy, and 28.82±14.26–153.27±55.80 nM against dominant cytosolic hCA II isoforms associated with glaucoma. Furthermore, the theoretical parameters of the bioactive molecules were calculated to establish their drug-likeness qualities. The proteins used for the calculations are prostate cancer protein (PDB ID: 3RUK and 6XXP). ADME/T analysis was carried out to examine the drug properties of the studied molecules. |
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Keywords: | anticancer agent carbonic anhydrase inhibitors hydrazone imidazole synthesis |
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