Synthesis and structural characterization of novel pyrazoline derivatives
Öz
Pyrazolines, which are nitrogen including five-membered heterocyclic structures, have been used in the organic and pharmaceutical industries. This study aimed was to synthesize and characterizes new series of 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives. The new pyrazoline compounds have been synthesized from chalcones and hydrazine hydrate in two steps. In the first step, chalcones were synthesized from 2-amino acetophenone and various substituted benzaldehyde by Claisen-Schmidt condensation at room temperature. In second step, starting from various substituted chalcones derivatives with hydrazine hydrate and glacial acetic acid in anhydrous ethanol were synthesized six novel 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives utilizing intramolecular Michael addition reaction in good yields. The structures of the newly synthesized 3,5-diphenyl-4,5-dihydro-1H-pyrazole derivatives are identified via 1H NMR, 13C NMR, FT-IR, and HRMS.
Anahtar Kelimeler
Kaynakça
- Abdel-Halim, M., Tinsley, H., keeton, A. B., Weam, M., Atta, N. H., Hammam, M. A., Hefnawy, A., Hartmann, R. W., Engel, M., Piazza, G. A. and Abadi, A. H. (2020). Discovery of trisubstituted pyrazolines as a novel scaffold for the development of selective phosphodiesterase 5 inhibitors. Bioorganic Chemistry, 104, 104322, https://doi.org/10.1016/j.bioorg.2020.104322.
- Ahmad, A., Husain, A., Khan, S. A., Mujeeb, M. and Bhandari, A. (2016). Synthesis, antimicrobial and antitubercular activities of some novel pyrazoline derivatives. Journal of Saudi Chemical Society, 20(5), 577-584, https://doi.org/10.1016/j.jscs.2014.12.004.
- Arslan, T., Çelik, G., Çelik, H., Şentürk, M., Yaylı, N. and Ekinci, D. (2016). Synthesis and Biological Evaluation of Novel Bischalcone Derivatives as Carbonic Anhydrase Inhibitors. Archiv der Pharmazie, 349(9), 741-748, https://doi.org/10.1002/ardp.201600122.
- Bano, S., Alam, M. S., Javed, K., Dudeja, M., Das, A. K. and Dhulap, A. (2015). Synthesis, biological evaluation and molecular docking of some substituted pyrazolines and isoxazolines as potential antimicrobial agents. European Journal of Medicinal Chemistry, 95, 96-103, https://doi.org/10.1016/j.ejmech.2015.03.031.
- Çelik, G., Arslan, T., Şentürk, M. and Ekinci, D. (2020). Synthesis and characterization of some new pyrazolines and their inhibitory potencies against carbonic anhydrases. Archiv der Pharmazie, 353(3), 1900292, https://doi.org/10.1002/ardp.201900292.
- Çelik, G. (2020). New chalcone-3-O-glycoside derivatives: Synthesis and characterization. Journal of Chemical Research, 44(9-10), 598-601, https://doi.org/10.1177/1747519820915165.
- Delgado, G. E., Liew, S. M., Jamalis, J., Cisterna, J., Cardenas, A. and Brito, I. (2020). Structural characterization and Hirsfeld surface analysis of the pyrazoline 1-(3-(4-iodophenyl)-5-(3-methylthiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl) ethan-1-one. Journal of Molecular Structure, https://doi.org/10.1016/j.molstruc.2020.128044.
- Dofe, V. S., Sarkate, A. P., Tiwari, S. V., Lokwani, D. K., Karnik, K. S., Kale, I. A., Dodamani, S., Jalalpure, S. S. and Burra, P. V. L. S. (2020). Ultrasound assisted synthesis of tetrazole based pyrazolines and isoxazolines as potent anticancer agents via inhibition of tubulin polymerization. Bioorganic & Medicinal Chemistry Letters, 30(22), 127592, https://doi.org/10.1016/j.bmcl.2020.127592.
- El Sayed Aly, M. R., El Razek Fodah, H. H .A. and Saleh, S. Y. (2014). Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes. European Journal of Medicinal Chemistry, 76, 517-530, https://doi.org/10.1016/j.ejmech.2014.02.021.
- Farooq, S. and Ngaini, Z. (2020). One-Pot and Two-Pot Synthesis of Chalcone Based Mono and Bis-Pyrazolines. Tetrahedron Letters, 61(4), 151416, https://doi.org/10.1016/j.tetlet.2019.151416.