Volume 4, Issue 2 (April 2025)                   Health Science Monitor 2025, 4(2): 131-139 | Back to browse issues page


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Afzal-Ahangaran S, Sharifi Y, Allahyari-Devin M. Development of novel antimicrobial agents: investigating the efficacy of 1,3,5-Triphenyl-2-pyrazoline derivatives. Health Science Monitor 2025; 4 (2) :131-139
URL: http://hsm.umsu.ac.ir/article-1-213-en.html
Department of Medicinal Chemistry, School of Pharmacy, Urmia University of Medical Sciences, Urmia, Iran
Abstract:   (140 Views)
Background & Aims: In this research, a novel series of heterocyclic compounds containing pyrazoline nuclei was synthesized in two steps.
Materials & Methods: In the first step, chalcones were prepared using the Claisen-Schmidt reaction between substituted benzaldehydes and acetophenone derivatives. In the second step, the chalcones were cyclized under acidic conditions with hydrazine derivatives to produce pyrazolines. All compounds were characterized through physical, chromatographic, spectroscopic, and elemental analyses, and their antibacterial properties were tested using seven microorganisms. The minimum inhibitory concentrations of all compounds were determined using the broth dilution method.
Results: Among them, compound 2f (4-(1, 5-diphenyl-4, 5-dihydro-1H-pyrazol-3-yl) phenol) exhibited the highest antibacterial and antifungal activity, making it the most potent compound in the series.
Conclusion:  These results indicate that increasing the polarity of the compounds enhanced their efficacy against Gram-positive strains, whereas derivatives containing at least one methoxy group in their structure suppressed Gram-negative growth.
Full-Text [PDF 416 kb]   (39 Downloads)    
Type of Study: Research | Subject: General
Received: 2024/12/7 | Accepted: 2025/04/6 | Published: 2025/04/30

References
1. Olczak-kowalczyk D, Daszkiewicz M, Krasuska-Sławińska E, Dembowska-Bagińska B, Gozdowski D, Daszkiewicz P, et al. Bacteria and Candida yeasts in inflammations of the oral mucosa in children with secondary immunodeficiency. Journal of oral pathology & medicine: official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology 2012; 41:568-76. doi: 10.1111/j.1600-0714.2012.01146.x. [DOI] [PMID]
2. Baker RE, Mahmud AS, Miller IF, Rajeev M, Rasambainarivo F, Rice BL, et al. Infectious disease in an era of global change. Nature Reviews Microbiology 2021; doi: 10.1038/s41579-021-00639-z. [DOI] [PMID] [PMCID]
3. Tuite N, Lacey K. Overview of Invasive Fungal Infections. Methods in molecular biology (Clifton, NJ) 2013; 968:1-23. doi: 10.1007/978-1-62703-257-5_1. [DOI] [PMID]
4. Dhingra S, Rahman NAA, Peile E, Rahman M, Sartelli M, Hassali MA, et al. Microbial Resistance Movements: An Overview of Global Public Health Threats Posed by Antimicrobial Resistance, and How Best to Counter. Frontiers in Public Health 2020; 8 doi: 10.3389/fpubh.2020.535668. [DOI] [PMID] [PMCID]
5. Agrawal M, Sonar PK, Saraf SK. Synthesis of 1,3,5-trisubstituted pyrazoline nucleus containing compounds and screening for antimicrobial activity. Med Chem Res 2012; 21(11):3376-81. doi: 10.1007/s00044-011-9871-2. [DOI]
6. Kerru N, Gummidi L, Maddila S, Gangu KK, Jonnalagadda SB. A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications. Molecules 2020; 25(8):1909. [DOI] [PMID] [PMCID]
7. Sapnakumari M, Narayana B, Gurubasavarajswamy P, Sarojini B. Design, synthesis, and pharmacological evaluation of new pyrazoline derivatives. Monatshefte für Chemie - Chemical Monthly 2015; 146:1015-24. doi: 10.1007/s00706-014-1371-x. [DOI]
8. Praceka MS, Megantara S, Maharani R, Muchtaridi M. Comparison of various synthesis methods and synthesis parameters of pyrazoline derivates. Journal of advanced pharmaceutical technology & research 2021; 12(4):321-6. doi: 10.4103/japtr.JAPTR_252_21. [DOI] [PMID] [PMCID]
9. Hamid Reza S, Yadollah Y, Ali E, Mehdi A. Extraction and determination of 2-pyrazoline derivatives using liquid phase microextraction based on solidification of floating organic drop. Journal of Pharmaceutical and Biomedical Analysis 2008; 48(4):1059-63. doi: https://doi.org/10.1016/j.jpba.2008.07.029 [DOI] [PMID]
10. Munawar M, Muhammad A, Makshoof A, Paul G. Synthesis and antimicrobial activity of quinoline-based 2-pyrazolines. Chemical Papers 2008; 62(3):288--93. doi: doi:10.2478/s11696-008-0025-z. [DOI]
11. Yin J, Wang Z. Ordered Self-Assembling of Tetrahedral Oxide Nanocrystals. Physical Review Letters 1997; 79 doi: 10.1103/PhysRevLett.79.2570. [DOI]
12. Sarojini B, Vidyagayatri M, Raj D, B.R B, Hanumanthappa M. DPPH Scavenging Assay of Novel 1,3-disubstituted-1H-pyrazol-5-ols and their in silico Studies on Some Proteins Involved in Alzheimer's Disease Signaling Cascade. Letters in Drug Design & Discovery 2010; 7:214-24. doi: 10.2174/157018010790596588. [DOI]
13. Sano T, Fujii T, Nishio Y, Hamada Y, Shibata K, Kuroki K. Pyrazoline Dimers for Hole Transport Materials in Organic Electroluminescent Devices. Japanese Journal of Applied Physics 1995; 34(Part 1, No. 6A):3124-7. doi: 10.1143/jjap.34.3124. [DOI]
14. Rajendra Prasad Y, Lakshmana Rao A, Prasoona L, Murali K, Ravi Kumar P. Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2″-hydroxy naphthalen-1″-yl)-1,5-diphenyl-2-pyrazolines. Bioorganic & Medicinal Chemistry Letters 2005; 15(22):5030-4. doi: 10.1016/j.bmcl.2005.08.040. [DOI] [PMID]
15. Parmar SS, Pandey BR, Dwivedi C, Harbison RD. Anticonvulsant Activity and Monoamine Oxidase Inhibitory Properties of 1,3,5-Trisubstituted Pyrazolines. Journal of Pharmaceutical Sciences 1974; 63(7):1152-5. doi: 10.1002/jps.2600630730. [DOI] [PMID]
16. Vamaraju HB, Manna S, Srinivasan K, Giliyaru V. Synthesis and biological evaluation of 1,3,5-trisubstituted pyrazolines bearing benzofuran. Indian Journal of Heterocyclic Chemistry 2004; 13:253-6. [Google Scholar]
17. Abid M, Azam A. Synthesis and antiamoebic activities of 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones. Bioorganic & medicinal chemistry 2005; 13:2213-20. doi: 10.1016/j.bmc.2004.12.050. [DOI] [PMID]
18. Sahu S, Banerjee M, Samantray A, Behera C, Azam A. Synthesis, Analgesic, Anti-inflammatory and Antimicrobial Activities of Some Novel Pyrazoline Derivatives. Tropical Journal of Pharmaceutical Research (ISSN: 1596-5996) Vol 7 Num 2 2008; 7 doi: 10.4314/tjpr.v7i2.14664. [DOI]
19. Patel V, Desai K. Eco-friendly synthesis of fluorine-containing pyrazoline derivatives over potassium carbonate. Arkivoc 2004; 2004. [DOI]
20. Chen Y, Lam Y, Lai Y-H. Solid-Phase Synthesis of Pyrazolines and Isoxazolines with Sodium Benzenesulfinate as a Traceless Linker. Organic Letters 2003; 5(7):1067-9. doi: 10.1021/ol0340888. [DOI] [PMID]
21. Soni N, Pande K, Kalsi R, Gupta TK, Parmar SS, Barthwal JP. Inhibition of rat brain monoamine oxidase and succinic dehydrogenase by anticonvulsant pyrazolines. Res Commun Chem Pathol Pharmacol 1987; 56(1):129-32. [Google Scholar]
22. Smith SR, Denhardt G, Terminelli C. The anti-inflammatory activities of cannabinoid receptor ligands in mouse peritonitis models. European Journal of Pharmacology 2001; 432(1):107-19. doi: 10.1016/S0014-2999(01)01477-7. [DOI] [PMID]
23. Sakthinathan SP, Vanangamudi G, Thirunarayanan G. Synthesis, spectral studies and antimicrobial activities of some 2-naphthyl pyrazoline derivatives. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2012; 95:693-700. doi: 10.1016/j.saa.2012.04.082. [DOI] [PMID]
24. Turan-Zitouni G, Chevallet P, Kiliç FS, Erol K. Synthesis of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity. European Journal of Medicinal Chemistry 2000; 35(6):635-41. doi: 10.1016/S0223-5234(00)00152-5. [DOI] [PMID]
25. Chimenti F, Fioravanti R, Bolasco A, Manna F, Chimenti P, Secci D, et al. Synthesis, molecular modeling studies and selective inhibitory activity against MAO of N1-propanoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives. European journal of medicinal chemistry 2008; 43(10):2262-7. doi: 10.1016/j.ejmech.2007.12.026. [DOI] [PMID]
26. Reddy MVR, Billa VK, Pallela VR, Mallireddigari MR, Boominathan R, Gabriel JL, et al. Design, synthesis, and biological evaluation of 1-(4-sulfamylphenyl)-3-trifluoromethyl-5-indolyl pyrazolines as cyclooxygenase-2 (COX-2) and lipoxygenase (LOX) inhibitors. Bioorganic & Medicinal Chemistry 2008; 16(7):3907-16. doi: 10.1016/j.bmc.2008.01.047. [DOI] [PMID]
27. Hasan A, Abbas A, Akhtar M. Synthesis, Characterization and Fluorescent Property Evaluation of 1,3,5-Triaryl-2-pyrazolines. Molecules (Basel, Switzerland) 2011; 16:7789-802. doi: 10.3390/molecules16097789. [DOI] [PMID] [PMCID]
28. Andrews JM. Determination of minimum inhibitory concentrations. Journal of antimicrobial Chemotherapy 2001; 48(suppl_1):5-16. [DOI] [PMID]

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