Alka Tyagi,
Pravin Roman,
Renuka Doiphode,
Sanjivani Chaudhary,
- Associate Professor Shri Pandit Baburao Chaughule College of Pharmacy, Thane Maharashtra India
- Associate Professor Shri Pandit Baburao Chaughule College of Pharmacy, Thane Maharashtra India
- Associate Professor Shri Pandit Baburao Chaughule College of Pharmacy, Thane Maharashtra India
- Associate Professor Shri Pandit Baburao Chaughule College of Pharmacy, Thane Maharashtra India
Abstract
Background: Schiff bases, a class of organic compounds, have garnered significant attention due to their diverse applications in various fields such as pharmaceuticals, materials science, and coordination chemistry. This abstract provides a comprehensive overview of the synthesis of Schiff bases amino pyridine derivatives and aromatic ketones along with their anti-microbial activity. Method: The synthesis of Schiff bases primarily involves the condensation reaction between a primary amine and a carbonyl compound (ketone) along with glacial acetic acid. Various methods have been developed for the synthesis of Schiff bases; Classical methods typically involve refluxing the amine and carbonyl compound in a suitable solvent with or without a catalyst. In these research nine new compounds of Schiff bases have been synthesized along with characterization and antibacterial and anti-fungal activities. Result: It was discovered that all elemental analysis, IR, 1H NMR, and mass spectrometry values were significant. According to antimicrobial and antifungal screening results, compounds PS-1 and compound PS-9 were found to be more active against all tested strains, while Schiff bases demonstrate substantial activity against Staphylococcus aureus and Candida albicans. PS-1 compound was found to have most activity in anti-bacterial test while PS-9 was found to possess best anti-fungal activity. Conclusion: The current study examines the pharmacological properties of pyridine derivatives. Pyridine derivative PS-1 was found to be most active antibacterial agent and PS-9 most active antifungal agent. The results of the study have important implications for future investigations into possible therapies for bacterial infections.
Keywords: Schiff base, Synthesis, Pharmacological evaluation, NMR spectroscopy, Pyridine derivatives.
[This article belongs to Research & Reviews: A Journal of Drug Design & Discovery(rrjoddd)]
References
1. Khedr AM, Jadon S, Kumar V. Synthesis, Spectral analysis, and molecular modeling of bioactive Sn (II)-complexes with oxadiazole Schiff bases. Journal of Coordination Chemistry. 2011 Apr 20;64(8):1351-9.
2. Tsacheva I, Todorova Z, Momekova D, Momekov G, Koseva N. Pharmacological activities of Schiff bases and their derivatives with low and high molecular phosphonates. Pharmaceuticals. 2023 Jun 28;16(7):938. https://doi.org/10.3390/ph16070938
3. Gul R, Munir W, Saleh EA, Shujah S, Sirajuddin M, Tabassum S, ur Rehman K, Khan D, Al-Saeedi SI, Abdelrahman EA. Ferrocene based Schiff bases and their complexes: Synthesis, characterization and biological evaluation. Journal of Organometallic Chemistry. 2024 Jan 1;(1003):122944. https://doi.org/10.1016/j.jorganchem.2023.122944
4. Gurav SS, Waghmode KT, Dandekar SN, Jadhav SD, Lotlikar OA, Jadhav SR, Mali SN, Naphade JG. New 2-Chloroimidazo [1, 2-a] pyridine induced Schiff bases: Synthesis, characterization, antimicrobial and A-498 and A-549 anticancer activity, molecular modeling, in-silico pharmacokinetics, and DFT studies. Chemical Physics Impact. 2024 Jun 1;8:100494.
5. Ceramella J, Iacopetta D, Catalano A, Cirillo F, Lappano R, Sinicropi MS. A review on the antimicrobial activity of Schiff bases: Data collection and recent studies. Antibiotics. 2022 Feb 1;11(2):191..
6. Mishra N, Kumar K, Pandey H, Anand SR, Yadav R, Srivastava SP, Pandey R. Synthesis, characterization, optical and anti-bacterial properties of benzothiazole Schiff bases and their lanthanide (III) complexes. Journal of Saudi Chemical Society. 2020 Dec 1;24(12):925-33.
7. Pandey Alok, Dewangan Dhansay, Verma Shekhar, Mishra Achal, Dhar Dubey Ravindra.Synthesis of Schiff Bases of 2-amino-5-aryl-1,3,4- thiadiazole and Its Analgesic. (n.d.). In Anti-Inflammatory and Anti-Bacterial Activity. International Journal of ChemTech Research,Vol. 3, No.1, pp 178-184.
8. Shahraki S, Majd MH, Heydari A. Novel tetradentate Schiff base zinc (II) complex as a potential antioxidant and cancer chemotherapeutic agent: Insights from the photophysical and computational approach. Journal of Molecular Structure. 2019 Feb 5;1177:536-44. https://doi.org/10.1016/j.molstruc.2018.10.005
9. Saedi Z, Hoveizi E, Roushani M, Massahi S, Hadian M, Salehi K. Synthesis, characterization, anticancer properties and theoretical study of asymmetrical Cd (II) N2-Schiff base complexes. Journal of Molecular Structure. 2019 Jan 15;1176:207-16. https://doi.org/10.1016/j.molstruc.2018.08.072
10.Shabbir, M., Akhter, Z., Ahmad, I., Ahmed, S., Ismail, H., Mirza, B., McKee, V., & Bolte, M. (2016). Synthesis, characterization, biological and electrochemical evaluation of novel ether based ON donor bidentate Schiff bases. Journal of Molecular Structure, 1116, 84–92. https://doi.org/10.1016/j.molstruc.2016.03.008
11. Deepika P, Vinusha HM, Begum M, Ramu R, Shirahatti PS, Prasad MN. 2-methoxy-4-(((5-nitropyridin-2-yl) imino) methyl) phenol Schiff base ligand and its Cu (II) and Zn (II) complexes: synthesis, characterization and biological investigations. Heliyon. 2022 Jun 1;8(6). https://doi.org/10.1016/j.heliyon.2022.e09648
12.Pouralimardan, O., Chamayou, A.-C., Janiak, C., & Hosseini-Monfared, H. (2007). Hydrazone Schiff base-manganese(II) complexes: Synthesis, crystal structure and catalytic reactivity. Inorganica Chimica Acta, 360(5), 1599–1608. https://doi.org/10.1016/j.ica.2006.08.056
13.Karvembu, R., Hemalatha, S., Prabhakaran, R., & Natarajan, K. (2003). Synthesis, characterization and catalytic activities of ruthenium complexes containing triphenylphosphine/triphenylarsine and tetradentate Schiff bases. Inorganic Chemistry Communications, 6(5), 486–490. https://doi.org/10.1016/s1387-7003(03)00021-2
14.İspir, E. (2009). The synthesis, characterization, electrochemical character, catalytic and antimicrobial activity of novel, azo-containing Schiff bases and their metal complexes. Dyes and Pigments: An International Journal, 82(1), 13–19. https://doi.org/10.1016/j.dyepig.2008.09.019
15.Mabad, B., Cassoux, P., Tuchagues, J. P., & Hendrickson, D. N. (1986). Manganese(II) complexes of polydentate Schiff bases. 1. Synthesis, characterization, magnetic properties, and molecular structure. Inorganic Chemistry, 25(9), 1420–1431. https://doi.org/10.1021/ic00229a025
16. Kaushik S, Paliwal SK, Iyer MR, Patil VM. Promising Schiff bases in antiviral drug design and discovery. Medicinal Chemistry Research. 2023 Jun;32(6):1063-76. https://doi.org/10.1007/s00044-023-03068-0
17. Joshi KK. Chemistry with Schiff bases of pyridine derivatives: Their potential as bioactive ligands and chemosensors. InExploring Chemistry with Pyridine Derivatives 2022 Oct 7. IntechOpen.
18. Jiang L, Tian Y, Cheng J, Zhang J. A biomass-based Schiff base vitrimer with both excellent performance and multiple degradability. Polymer Chemistry. 2021;12(45):6527-37.https://doi.org/10.1039/d1py01003d
19 . Sztanke M, Wilk A, Sztanke K. An Insight into Fluorinated Imines and Hydrazones as Antibacterial Agents. International Journal of Molecular Sciences. 2024 Mar 15;25(6):3341.
20. Zhao J, Xie Y, Fang J, Ling Y, Gao Y, Liu X, Zhang Q, Xu Q, Xiong H. P-phenylenediamine-benzoquinone Schiff base Ag (I) complexes chemically bonded to few-layered graphene as flexible materials for electromagnetic studies. Journal of Materials Science. 2016 Dec;51:10574-84.
21 . Cui J, Sun Y, Wang L, Miao Q, Tan W, Guo Z. Preparation of l-arginine schiff bases modified chitosan derivatives and their antimicrobial and antioxidant properties. Marine Drugs. 2022 Oct 31;20(11):688.https://doi.org/10.3390/md20110688
22.John C. Christenson, E. Kent Korgenski, Ryan F. Relich, 286 – Laboratory Diagnosis of Infection Due to Bacteria, Fungi, Parasites, and Rickettsiae, Editor(s): Sarah S. Long, Charles G. Prober, Marc Fischer, Principles and Practice of Pediatric Infectious Diseases (Fifth Edition), Elsevier, 2018, Pages 1422 1434.e3, https://asm.org/getattachment/2594ce26-bd44-47f6-8287-0657aa9185ad/Kirby-Bauer-Disc-Diffusion- Susceptibility-Test-Protocol-pdf.pdf
23.https://asm.org/getattachment/2594ce26-bd44-47f6-8287-0657aa9185ad/Kirby-Bauer-Disk-Diffusion-Susceptibility-Test-Protocol-pdf.pdf
John C. Christenson, E. Kent Korgenski, Ryan F. Relich, 286 – Laboratory Diagnosis of Infection Due to Bacteria, Fungi, Parasites, and Rickettsiae, Editor(s): Sarah S. Long, Charles G. Prober, Marc Fischer, Principles and Practice of Pediatric Infectious Diseases (Fifth Edition), Elsevier, 2018, Pages 1422 1434.e3,
Research & Reviews: A Journal of Drug Design & Discovery
Volume | 11 |
Issue | 02 |
Received | July 4, 2024 |
Accepted | July 26, 2024 |
Published | August 12, 2024 |