New Pyrazoline Derivatives Containing Imine Moiety: Synthesis, Characterization and Antimicrobial Study
DOI:
https://doi.org/10.23851/mjs.v32i3.955Keywords:
Chalcone, Pyrazoline, Schiff base and antimicrobial.Abstract
A new series of pyrazoline derivatives (3-10) have been synthesized and characterized on the basis of FT-IR, 1H-NMR, and Mass techniques. 1-(4-Aminophenyl)-3-(pyridin-4-yl)prop-2-en-1-one (1) as a starting material was prepared by the reaction of 4-aminoacetophenone and 4-pyridinecarboxaldehyde in ethanol, using sodium hydroxide as a catalyst. Pyrazoline derivatives 2 was obtained via the cyclization reaction of compound 1 by the action of hydrazine hydrate 80% in ethanol. The target derivatives (3-8) were obtained by the reaction of pyrazoline derivative (2) with the corresponding aldehyde in ethanol. The novel pyrazoline derivatives 9 and 10 were synthesized by the reaction of pyrazoline derivative 2 with the corresponding anhydride (maleic or phthalic anhydride) in presence of anhydrous sodium acetate in glacial acetic acid. The synthesized derivatives were screened against several bacterial strains: Staphylococcus aureus, Staphylococcus espidermididis, Escherichia coli, Klebsiella and Candida albicans. The synthesized compounds showed promising bio-activity compared with amoxicillin.
Downloads
References
B. Varghese, S. N. Al-Busafi, F. O. Suliman, and S. M. Z. Al-Kindy, "Unveiling a versatile heterocycle: pyrazoline-a review," RSC Adv., vol. 7, no. 74, pp. 46999-47016, 2017.
R. A. Mekheimer, E. A. Ahmed, and K. U. Sadek, "Recent developments in the chemistry of pyrazolo [4, 3-c] quinolines," Tetrahedron (Oxford. Print), vol. 68, no. 6, 2012.
S. D. Joshi et al., "Synthesis, antimycobacterial screening and ligand-based molecular docking studies on novel pyrrole derivatives bearing pyrazoline, isoxazole and phenyl thiourea moieties," Eur. J. Med. Chem., vol. 107, pp. 133-152, 2016.
A. P. S. Bonakdar, A. Sadeghi, H. R. Aghaei, K. Beheshtimaal, S. M. R. Nazifi, and A. R. Massah, "Convenient synthesis of novel chalcone and pyrazoline sulfonamide derivatives as potential antibacterial agents," Russ. J. Bioorganic Chem., vol. 46, no. 3, pp. 371-381, 2020.
B. P. Bandgar et al., "Bioorganic & Medicinal Chemistry Letters Synthesis , biological evaluation , and docking studies of 3- ( substituted ) -aryl-5- ( 9-methyl-3-carbazole ) -1 H -2-pyrazolines as potent anti-inflammatory and antioxidant agents," Bioorg. Med. Chem. Lett., vol. 22, no. 18, pp. 5839-5844, 2012, doi: 10.1016/j.bmcl.2012.07.080.
N. C. Desai, D. V Vaja, K. A. Jadeja, S. B. Joshi, and V. M. Khedkar, "Synthesis, Biological Evaluation and Molecular Docking Study of Pyrazole, Pyrazoline Clubbed Pyridine as Potential Antimicrobial Agents," Anti-Infective Agents, vol. 18, no. 3, pp. 306-314, 2020.
B. B. Dias et al., "Synthesis, structural characterization, and prospects for new cobalt (II) complexes with thiocarbamoyl-pyrazoline ligands as promising antifungal agents," J. Inorg. Biochem., vol. 213, p. 111277, 2020.
P. Kumari, V. S. Mishra, C. Narayana, A. Khanna, A. Chakrabarty, and R. Sagar, "Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents," Sci. Rep., vol. 10, no. 1, pp. 1-16, 2020.
pp. 154-63. Kumar, SureshKumar, Suresh, et al. "Biological Activities of Pyrazoline Derivatives-A Recent Development." Recent Patents on Anti-Infective Drug Discovery, vol. 4, no. 3, Bentham Science Publishers, 2009, S. Bawa, S. Drabu, R. Kumar, and H. Gupta, "Biological activities of pyrazoline derivatives-A recent development," Recent Pat. Antiinfect. Drug Discov., vol. 4, no. 3, pp. 154-163, 2009.
F. Turkan, A. Cetin, P. Taslimi, H. S. Karaman, and İ. Gulçin, "Synthesis, characterization, molecular docking and biological activities of novel pyrazoline derivatives," Arch. Pharm. (Weinheim)., vol. 352, no. 6, p. 1800359, 2019.
O. J. Mohammed, M. F. Radi, A. M. Abdula, B. W. Al-ahdami, W. F. Rodhan, and H. G. S. H. A. Aban, "SYNTHESIS OF FOUR CHALCONE DERIVATIVES BEARING HETEROCYLIC MOIETIES AS NEW AChE INHIBITORS BY DOCKING SIMULATION," Int. J. Chem. Sci. vol. 13, no. 1, pp. 157-166, 2015.
M. T. Mohammed and A. Abdula, "Derivatives as New Antimicrobial Agents : Synthesis , Characterization and Docking Study,"Intern. J. Chem. Sci. vol.15 Iss 2 no. July, 2017.
G. L. Mohsen, A. M. Abdula, A. Mohammed, and N. Jassim, "Synthesis , Antimicrobial , Antioxidant and Docking Study of Novel Isoxazoline Derivatives," Acta Pharm. Sci. vol. 56, no. 3, pp. 2-8, 2018, doi: 10.23893/1307-2080.APS.05619.
K. Kankanala, V. R. Reddy, K. Mukkanti, and S. Pal, "Lewis acid free high speed synthesis of nimesulide-based novel N-substituted cyclic imides," J. Braz. Chem. Soc., vol. 21, no. 6, pp. 1060-1064, 2010, doi: 10.1590/S0103-50532010000600015.
[F. Fatima, S. H. Bhat, M. F. Ullah, F. Abu-duhier, and E. Husain, "In-Vitro Antimicrobial Activity of Herbal Extracts From Tabuk Region ( Kingdom of Saudi Arabia ) Against Nosomial Pathogens : A Preliminary Study," vol. 10, no. 3, pp. 83-89, 2018, doi: 10.5539/gjhs.v10n3p83.
Downloads
Key Dates
Published
Issue
Section
License
Articles accepted for publication in Al-Mustansiriyah Journal of Science (MJS) are protected under the Creative Commons Attribution 4.0 International License (CC BY-NC). Authors of accepted articles are requested to sign a copyright release form prior to their article being published. All authors must agree to the submission, sign copyright release forms, and agree to be included in any correspondence between MJS and the authors before submitting a work to MJS. For personal or educational use, permission is given without charge to print or create digital copies of all or portions of a MJS article. However, copies must not be produced or distributed for monetary gain. It is necessary to respect the copyright of any parts of this work that are not owned by MJS.
How to Cite
