- All Journals
- Al-Qadisiyah University
- Basrah University
- Kirkuk University
- Mosul University
- The Iraqi Borad for Medical Specialization
- University of Anbar
- University of Technology
- Al Mustafa University
- Al-Zahraa University for Women
- Alnoor University
- Kunooz University
- Misan University
- Ninevah University
- Tikrit University
- University of Al-Hamdaniya
- University of Kerbala
Synthesis of Some New Derivatives of Pyrrolidine-2-one and Studying Their Antibacterial Potentials | ||
| Engineering and Technology Journal | ||
| Article 5, Volume 38, 3B, 2020, Pages 128-141 PDF (1.43 M) | ||
| Document Type: Research Paper | ||
| DOI: 10.30684/etj.v38i3B.706 | ||
| Authors | ||
| Nadia A. Betti* 1; Redha Ib. Hussain2; Sahar Ab. Kadhem2 | ||
| 1Materials Engineering Department, University of Technology, Baghdad, Iraq | ||
| 2Department of Chemistry, Mustansiriyah University, Baghdad, Iraq. | ||
| Abstract | ||
| New derivatives of pyrrolidine-2-one have been synthesized through lactamization of γ –butyrolactone (GBL) by hydrazine hydrate (80%), ethylene diamine and ethanol amine to afford compounds (1-aminopyrrolidin-2-one), (1-(2-aminoethyl)pyrrolidine-2-one) and (1-(2-hydroxyethyl)pyrrolidine-2-one), respectively. Compound (1-aminopyrrolidin-2-one) underwent several reactions to synthesize the rest of these derivatives. All synthesized compounds were approved by their FT-IR, 1H-NMR and some by Mass spectra. The biological activities of these derivatives were evaluated against Escherichia coli and Staphylococcus aureus. Many of these derivatives showed moderate biological activity against one or both kind of bacteria in comparison to amoxicillin and some showed no biological activity at all. | ||
| Keywords | ||
| Pyrrolidine-2-one; Lactamization; biological activity | ||
| References | ||
|
[1] Z. Hosseinzadeh, A. Ramazani, K. Hosseinzadeh, N. Razzaghi-AsI and F. Gouranlou, "An Overview on Chemistry and Biological Importance of Pyrrolidinone, "Current Org. Synthesis, 14, 1-13, 2017. [2] R. Vogelsang, R. Pinkos, U. Mahn, et al," Ullmann's encyclopedia of industrial chemistry," 7th edition, John Wiley & Sons, West Sussex, England, 2011. [3] K. Setrak, S. R. Tanielyan, R. L. More, T. T. Augustine, R. Kirk, S. Mark and G. Joseph," Hydrogenation of Succinimide to 2-Pyrrolidone Over Solid Catalysts, J. Top Catal., 57, 1582–1587, 2014. [4] K. Kim and S. H. Hong, "Iridium-Catalyzed Single-Step N Substituted Lactam Synthesis from Lactones and Amines," J. Org. Chem., 8, 4152-4156, 2015. [5] T. Yang, C. Lee, W. Huang and A. Lee, "Synthesis and Evaluation of Novel 2-Pyrrolidone-Fused (2-Oxoindolin-3-ylidene) methylpyrrole Derivatives as Potential Multi-Target Tyrosine Kinase Receptor Inhibitors," Molecule, 22, 2–18, 2017. [6] K. M. Koczkur, S. Mourdikoudis, L. Polavarapu and S. E. Skrabalak, "Polyvinylpyrrolidone (PVP) in Nanoparticle Synthesis," Dalton Trans., 44, 17883-17905. [7] J. Wu, W. Zhou, Q. Cheng and J. Yang," Poly Vinyl Pyrrolidone-Stabilized Magnetic Nickel Nanochains for Cancer Hyperthermia and Catalysis Applications," RSC Adv., 5, 22965–22971, 2015. [8] J.D. Vidal, M.J. Climent, A. Corma, D.P. Concepcion and S. Iborra, " One Pot Selective Catalytic Synthesis of Pyrrolidone Derivatives from Ethyl Levulinate and Nitro Compounds," Chem. Sus. Chem, 10, 119-128, 2017. [9] E. S. Ostroglyadov, O. S. Vasil’eva, S. M. Aleksandrovab, V. V. Pelipko, V. M. Berestovitskaya, I. N. Tyurenkov and V. V. Bagmetova," Indole-Containing Derivatives of α-Pyrrolidone: Synthesis and Structure, " Russian Journal of General Chemistry, 85, 1838–1844, 2015. [10] A. Nagaraja, Y. Puttaiahgowda, A. Kulal, A. M. Parambil and T. Varadavenkatesan," Synthesis, Characterization, and Fabrication of Hydrophilic Antimicrobial Polymer Thin Film Coatings," Macromolecular Res., 27, 301–309, 2019. [11] F. D. Schouwer, S. Adriaansen, L. Claesa and D. E. D. Vos," Bio-Based N-Alkyl-2-Pyrrolidones By Pd-Catalyzed Reductive N-Alkylation and Decarboxylation of Glutamic Acid, "Green Chem., 20, 1-22, 2017. [12] P. Hemalatha, M. Veeraiah, S.P. Kumar, K. Vanasuya, M. Manju and R. Naika, "Antibacterial Properties of Poly (N-Vinyl Pyrrolidone-Co-Acrylic Acid)/Diethyl Amino Ethanol Ester," IJACS, 2, 50-54, 2014. [13] L. Jiang, C. Cheng and L. Dong, "Synthesis and Antitumor Activity of a Novel Series of Helicid-Pyrrolidone Derivatives," Chem. Nat. Compd., 51, 121-126, 2015. [14] C. Zhuang, Z. Miao, L. Zhu, G. Dong, Z. Guo, and S. Wang," Discovery, Synthesis, and Biological Evaluation of Orally Active Pyrrolidone Derivatives As Novel Inhibitors of p53−MDM2 Protein− Protein Interaction," J. Med. Chem., 55, 9630-9642, 2012. [15] D. Michael, T. H. N. Thi and L. Jochen," Investigations into The Mechanism of Lactamization of Lactones Yielding in a Novel Route to Biologically Active Tryptamine Derivatives, Tetrahedron, 60, 4567–4578, 2004. [16] G.Y. Nagesh and B.H.M. Mruthyu-njayaswamy, "Synthesis, Characterization and Biological Relevance of Some Metal (II) Complexes with Oxygen, Nitrogen and Oxygen (ONO) Donor Schiff Base Ligand Derived From Thiazole and 2-Hydroxy-1-Naphthaldehyde," J. Molec. Structure, 1085, 198–206, 2015. [17] N. N. Majeed, A. H. Esaa and A. A. Turki, "Synthesis and Characterization of Some New Dimeric Imines and Dispiro Bicyclo-γ-Lactam," Der Pharma Chemica, 6, 288-293, 2014. [18] R. M. Mohareb, K. A. El-sharkawy, M. M. Hussein and H. M. El-sehrawi, "Synthesis of Hydrazide –Hydrazone Derivatives and Their Evaluation of Antidepressant ,Sedative and Analgesic Agents, "J. Pharm. Sci. Res.,2, 185-196, 2010. [19] M. A. Hassan , G. H. Sayed, A. M. El-Nagar and A. M. Hussien, "A Convenient Synthesis of Some Diarylurea and Thiourea Derivatives as Antimicrobial Compounds," Chem. Process Eng. Res., 25, 1-11, 2014. [20] L. S. Ahamed, "Synthesis and Characterization of New N-Substituted Quinoline-2-One Derivatives and Evaluation of Their Biological Activity," PhD. Thesis, Chemistry Dep., College of Science, Mustansiriya Univ., Iraq, 2016. [21] R. Abdul-Hussein, "Synthesis, Characterization and Evaluation of Antimicrobial Activity for Some New Heterocyclic Derivatives Containing Five, Six Rings," M. Sc. Thesis, Univ. of Baghdad, Iraq, 2014. [22] Z. B. Hashim," Synthesis, Characterization, and Antibacterial Study of New Benzo [b] Thiophene Derivatives," PhD. Thesis, Univ. Mustansiriya, Iraq, 2018. [23] N. H. Karam, J. H. Tomma and A. H. AL-dujaili, "Synthesis and Characterization of Heterocyclic Compounds Derived From 4- Hydroxy and 4-Amino Acetophenone," Ibn AL-Haitham J. Pure Appl. Sc., 26, 296-312, 2017. [24] R. B. Toch, V. M. Patil, S. A. Chaudhari, S.M. Chavan and R. W. Sabnis," Green Synthesis of Pyrazole and Oxazole Derivatives," J. Heterocyclic Chem, 56, 38-43, 2019. [25] M. Balouiri, M. Sadiki and S. K. Ibnsouda," Methods for In Vitro Evaluating Antimicrobial Activity: A review," J. Pharm. Anal., 6, 71–79, 2016. [26] P. Murray, K. Rosenthal and M. Pfaller, "Medical Microbiology," 8th Edition, Elsevier, 2015. [27] B. Khameneh, M. Iranshahy, V. Soheili and B. S. F. Bazzaz," Review on Plant Antimicrobials: a Mechanistic Viewpoint," Antimicrob. Resist. Infect. Control, 8, 1-28, 2019. [28] R. M. Epand, C. Walker, R. F. Epand and N. A. Magarvey," Molecular Mechanisms of Membrane Targeting Antibiotics," Biochimica et Biophysica Acta (BBA) - Biomembranes, 1858, 980-987, 2016. [29] M. A. Kohanski, D. J. Dwyer and J. J. Collin," How Antibiotics Kill Bacteria: From Targets to Networks," Natural Rev. Microbiol., 8, 423-435, 2010. [30] R.B. Ghool and S.M. Thatte, " Inhibition of Cell Wall Synthesis -Is This the Mechanism of Action of Penicillin?" Medical Hypotheses, 44, 127-131, 1995. [31] P. Sarkar, V. Yarlagadda, C. Ghosh and J. Haldar," A review of Cell Wall Synthesis Inhibitors with Emphasis on Glycopeptide," Antibiotics, 3,.1-20, 2017 | ||
|
Statistics Article View: 396 PDF Download: 410 |
||