Green Synthesis, Characterization and Bioactivity Evaluation of Bis (5-((1H-Imidazol)Methyl)-3-Phenylimidazolidin) Derivatives
Keywords:
Green Chemistry, Imidazole, Biological activity, Laser activityAbstract
This study describes the environmentally friendly synthesis of novel imidazole derivatives by the use of both conventional and microwave techniques to react Schiff bases with histidine in ethanol. Despite their importance in medicinal chemistry, imidazole molecules are still difficult to synthesize efficiently. The research included the preparation of new imidazole derivatives by reacting prepared Schiff bases with the amino acid histidine in the presence of ethanol as a solvent. The reaction was carried out using conventional and microwave methods, and the progress of the reaction was monitored and described by determining the melting point and purity. The Rf values were determined using thin-layer chromatography (T.L.C.), infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (1H-NMR), and quantitative elemental analysis (C.H.N.). The biological activity of the synthesised compounds was evaluated by examining their effect on the growth of four antibiotic-resistant bacterial isolates: Gram-negative (Escherichia) and Gram-positive (Staphylococcus aureus). The antibiotic Amoxicillin was used as a control sample. The prepared compounds showed good inhibitory activity against the tested bacteria. Furthermore, the laser activity of the synthesized composites was measured using a helium-neon laser (visible laser). The composites were exposed to radiation for four different time periods (15, 30, 45, 60) seconds, and their physical properties were re-examined to observe any changes caused by the laser exposure.
References
L. Zhang, X. M. Peng, G. L. Damu, R. X. Geng, and C. H. Zhou, "Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry," Med. Res. Rev., vol. 34, no. 2, pp. 340-437, 2014.
N. S. Khab, Z. Rezaei, M. Eskandari, A. Khalafinezhad, and M. Motazedian, "Synthesis of Metronidazole Derivatives as Antigiardiasis Agents," unpublished, 2007.
H. van den Bossche, "Biochemical Effects of Miconazole on Fungi—I: Effects on the Uptake and/or Utilization of Purines, Pyrimidines, Nucleosides, Amino Acids and Glucose by Candida albicans," Biochem. Pharmacol., vol. 23, no. 4, pp. 887-899, 1974.
H. Che, T. N. Tuyen, H. P. Kim, and H. Park, "1, 5-Diarylimidazoles with Strong Inhibitory Activity Against COX-2 Catalyzed PGE2 Production from LPS-Induced RAW 264.7 Cells," Bioorg. Med. Chem. Lett., vol. 20, no. 14, pp. 4035-4037, 2010.
P. Zhan, X. Liu, J. Zhu, Z. Fang, Z. Li, C. Pannecouque, and E. De Clercq, "Synthesis and Biological Evaluation of Imidazole Thioacetanilides as Novel Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors," Bioorg. Med. Chem., vol. 17, no. 16, pp. 5775-5781, 2009.
V. K. Kapoor, R. Chadha, P. K. Venisetty, and S. Prasanth, "Medicinal Significance of Nitroimidazoles—Some Recent Advances," unpublished.
D. Pectasides, H. Yianniotis, N. Alevizakos, D. Bafaloukos, V. Barbounis, J. Varthalitis, and A. Athanassiou, "Treatment of Metastatic Malignant Melanoma with Dacarbazine, Vindesine and Cisplatin," Br. J. Cancer, vol. 60, no. 4, pp. 627-629, 1989.
F. M. Muhammad, B. A. Khairallah, M. J. Saleh, and J. N. Saleh, "Preparation and Characterization of New Rings of Oxazine Derivatives and Studying Their Biological and Laser Effectiveness and Molecular Docking," Cent. Asian J. Theor. Appl. Sci., vol. 5, no. 4, pp. 190-201, 2024.
M. M. Aftan, M. A. Toma, A. H. Dalaf, E. Q. Abdullah, and H. K. Salih, "Synthesis and Characterization of New Azo Dyes Based on Thiazole and Assess the Biological and Laser Efficacy for Them and Study Their Dyeing Application," Egypt. J. Chem., vol. 64, no. 6, pp. 2903-2911, 2021.
A. H. Dalaf, F. H. Jumaa, and H. K. Salih, "Preparation, Characterization, Biological Evaluation and Assess Laser Efficacy for New Derivatives of Imidazolidin-4-One," Int. Res. J. Multidiscip. Technov., vol. 3, no. 4, pp. 41-51, 2021.
H. Dalaf, F. H. Jumaa, and H. K. Salih, "Multidisciplinary Technovation Red," Int. Res. J. Multidiscip. Technov., vol. 15, no. A2, p. C44H36N10O8, 2021.
H. Dalaf, "Synthesis and Characterization of Some Quartet and Quinary Heterocyclic Rings Compounds by Traditional Method and Microwave Routes Method and Evaluation of Their Biological Activity," M.S. thesis, Tikrit Univ., Tikrit, Iraq, 2018.
H. Dalaf and F. H. Jumaa, "Synthesis, Characterization of Some 1,3-Oxazepane-4,7-Dione by Traditional and Microwave Routes Method and Evaluation of Their Biological Activity," Al-Utroha Pure Sci., vol. 8, pp. 93-108, 2018.
H. Dalaf, F. H. Jumaa, and S. A. S. Jabbar, "Synthesis and Characterization of Some 2,3-Dihydroquinozoline and Evaluation of Their Biological Activity," Tikrit J. Pure Sci., vol. 23, no. 8, pp. 66-67, 2018.
S. A. J. Salwa, L. H. Ali, A. H. Adil, and H. S. A. Hossam, "Synthesis and Characterization of Azetidine and Oxazepine Compounds Using Ethyl-4-((4-Bromo Benzylidene) Amino) Benzoate as Precursor and Evaluation of Their Biological Activity," J. Educ. Sci. Stud., vol. 16, no. 5, pp. 39-52, 2020.
Q. Abd, H. I. Ibrahim, H. M. Jirjes, and A. H. Dalaf, "Synthesis and Identification of New Compounds with Antioxidant Activity Beta-Carotene from Natural Auxin Phenyl Acetic Acid," Res. J. Pharm. Technol., vol. 13, no. 1, pp. 40-46, 2020.
A. H. Dalaf and F. H. Jumaa, "Synthesis, Identification and Assess the Biological and Laser Efficacy of New Compounds of Azetidine Derived from Benzidine," Muthanna J. Pure Sci., vol. 7, no. 2, pp. 12-25, 2020.
M. M. Al-Tufah, S. S. Jasim, and K. A. Al-Badrany, "Synthesis and Antibacterial Evaluation of Some New Pyrazole Derivatives," Prof. Dr. R. K. Sharma, vol. 20, no. 3, p. 178, 2020.
A. Yass, M. M. Aftan, A. H. Dalaf, and F. H. Jumaa, "Synthesis and Identification of New Derivatives of Bis-1,3-Oxazepene and 1,3-Diazepine and Assess the Biological and Laser Efficacy for Them," Second Int. & Fourth Sci. Conf. Coll. Sci., Tikrit Univ., pp. 77-87, Nov. 2020.
D. Salih, A. H. Dalaf, M. A. Alheety, W. M. Rashed, and I. Q. Abdullah, "Biological Activity and Laser Efficacy of New Co (II), Ni (II), Cu (II), Mn (II) and Zn (II) Complexes with Phthalic Anhydride," Mater. Today: Proc., vol. 43, pp. 869-874, 2021.
M. M. Aftan, M. Q. Jabbar, A. H. Dalaf, and H. K. Salih, "Application of Biological Activity of Oxazepine and 2-Azetidinone Compounds and Study of Their Liquid Crystalline Behavior," Mater. Today: Proc., vol. 43, pp. 2040-2050, 2021.
A. Khairallah, F. M. Muhammad, J. N. Saleh, and M. J. Saleh, "Preparation, Characterization, Biological Activity Evaluation, and Liquid Crystallography Study of New Diazepine Derivatives," World Med. J. Biomed. Sci., vol. 1, no. 7, pp. 65-76, 2024.
M. J. Saleh, J. N. Saleh, K. Al-Badrany, A. H. Dalaf, R. S. Najm, and A. W. A. S. Talluh, "Preparation and Evaluation of the Biological Activity of a 2-Amino Pyran Ring Using a Solid Base Catalyst," Cent. Asian J. Med. Nat. Sci., vol. 5, no. 4, pp. 130-138, 2024.
A. W. A. S. Talluh, M. J. Saleh, and J. N. Saleh, "Preparation, Characterisation and Study of the Molecular Docking of Some Derivatives of the Tetrazole Ring and Evaluation of Their Biological Activity," World Med. J. Biomed. Sci., vol. 1, no. 7, pp. 15-23, 2024.
M. J. Saleh, J. N. Saleh, and K. Al-Badrany, "Preparation, Characterization, and Evaluation of the Biological Activity of Pyrazoline Derivatives Prepared Using a Solid Base Catalyst," Eur. J. Mod. Med. Pract., vol. 4, no. 7, pp. 25-32, 2024.
N. Saleh and A. Khalid, "Synthesis, Characterization and Biological Activity Evaluation of Some New Pyrimidine Derivatives by Solid Base Catalyst Al2O3-OBa," Cent. Asian J. Med. Nat. Sci., vol. 4, no. 4, pp. 231-239, 2023.
A. W. A. S. Talluh, M. J. Saleh, J. N. Saleh, K. Al-Badrany, and H. M. M. Saleh Al-Jubori, "Preparation, Characterization, and Evaluation of the Biological Activity of New 2,3-Dihydroquinazoline-4-One Derivatives," Eur. J. Mod. Med. Pract., vol. 4, no. 4, pp. 326-332, 2024.
W. A. S. Talluh, "Preparation, Characterization, Evaluation of Biological Activity, and Study of Molecular Docking of Azetidine Derivatives," Cent. Asian J. Med. Nat. Sci., vol. 5, no. 1, pp. 608-616, 2024.
H. Dalaf, M. J. Saleh, and J. N. Saleh, "Green Synthesis, Characterization, and Multifaceted Evaluation of Thiazolidinone Derivatives: A Study on Biological and Laser Efficacy," Eur. J. Mod. Med. Pract., vol. 4, no. 7, pp. 155-168, 2024.
W. A. S. Sattar Talluh, J. N. Saleh, M. J. Saleh, and H. M. Saleh Al-Jubori, "Preparation and Characterization of New Imidazole Derivatives Derived from Hydrazones and Study of Their Biological and Laser Efficacy," Cent. Asian J. Theor. Appl. Sci., vol. 5, no. 4, pp. 202-211, 2024.
H. Dalaf, "3-Phenylimidazolidin-4-One: Characterization, Green Synthesis, Evaluation of Biological and Laser Performance," Eur. J. Mod. Med. Pract., vol. 4, no. 7, pp. 417-427, 2024.
W. A. S. Talluh, J. N. Saleh, and M. J. Saleh, "Preparation, Characterization and Evaluation of Biological Activity and Study of Molecular Docking of Some New Thiazolidine Derivatives," unpublished, 2024.
H. Dalaf, F. H. Jumaa, M. M. Aftana, H. K. Salih, and I. Q. Abd, "Synthesis, Characterization, Biological Evaluation, and Assessment Laser Efficacy for New Derivatives of Tetrazole," in Key Eng. Mater., vol. 911, pp. 33-39, Trans Tech Publications Ltd, 2022.
H. Dalaf, F. H. Jumaa, and I. A. Yass, "Synthesis, Characterization, Biological Evaluation, Molecular Docking, Assess Laser Efficacy, Thermal Performance and Optical Stability Study for New Derivatives of Bis-1, 3-Oxazepene and 1, 3-Diazepine," in AIP Conf. Proc., vol. 2394, no. 1, AIP Publishing, Nov. 2022.
M. M. Saleh and F. H. Juma, "Synthesis, Characterization, and Study of Biological Activity of Oxazepine Compounds Derived from 1, 3, 4-Oxadiazole," Cent. Asian J. Med. Nat. Sci., vol. 5, no. 1, pp. 224-232, 2024.
A. I. Owed, A. A. Al-Jubouri, and S. Y. Al-Samarrai, "A Nano-Sensor for Copper Oxide Was Manufactured and Developed Using a New Organic Precipitant via Green Chemistry Methods," Sensors Mach. Learn. Appl., vol. 1, no. 1, 2024.
W. A. S. Talluh, R. S. Najm, M. J. Saleh, and J. N. Saleh, "Synthesis, Characterization, and Evaluation of the Biological Activity of Novel Oxazepine Compounds Derived from Indole-5-Carboxylic Acid," Am. J. Biosci. Clin. Integrity, vol. 1, no. 8, pp. 10-19, 2024.
M. M. Saleh, A. L. Al-Nassiry, J. N. Saleh, and M. J. Saleh, "Preparation and Diagnosis of New Complexes for Hg (II) with 4-Amino Acetanilide and (Dppp) as a Ligand and Study of the Bacterial Efficacy and Molecular Docking of the Prepared Complexes," Cent. Asian J. Theor. Appl. Sci., vol. 5, no. 4, pp. 364-373, 2024.
A. W. A. S. Talluh, M. J. Saleh, and J. N. Saleh, "Application of Infrared and Nuclear Magnetic Resonance Spectra in Studying the Bacterial Efficacy of Some Oxazepane Derivatives Derived from Hydrazones," Sensors Mach. Learn. Appl., vol. 3, no. 3, 2024. doi: 10.69534/smla/193913.
M. M. Aftan, A. A. Talloh, A. H. Dalaf, and H. K. Salih, "Impact Para Position on Rho Value and Rate Constant and Study of Liquid Crystalline Behavior of Azo Compounds," Mater. Today: Proc., vol. 45, pp. 5529-5534, 2021.
S. D. Khalaf, N. A. A. S. Ahmed, and A. H. Dalaf, "Synthesis, Characterization and Biological Evaluation (Antifungal and Antibacterial) of New Derivatives of Indole, Benzotriazole and Thioacetyl Chloride," Mater. Today: Proc., vol. 47, no. 17, pp. 6201-6210, 2021.
A. H. Dalaf, F. H. Jumaa, and H. K. Salih, "Preparation, Characterization, Biological Evaluation and Assess Laser Efficacy for New Derivatives of Imidazolidin-4-One," Int. Res. J. Multidisciplinary Technovation, vol. 3, no. 4, pp. 41-51, 2021.
H. Dalaf, F. H. Jumaa, and H. K. Salih, "Multidisciplinary Technovation," Red, vol. 15, no. A2, p. C44H36N10O8, 2021.
Y. Kh. Alasadi, F. H. Jumaa, A. H. Dalaf, S. M. Shawkat, and M. Gh. Mukhlif, "Synthesis, Characterization, and Molecular Docking of New Tetrazole Derivatives as Promising Anticancer Agents," J. Pharm. Negative Results, vol. 13, no. 3, pp. 513-522, 2022.
Y. K. Alasadi, F. H. Jumaa, and A. H. Dalaf, "Synthesis, Identification, Antibacterial Activity and Laser Effect of New Derivatives of Bis-1, 3-Oxazepene-4, 7-Dione and 1, 3-Diazepine-4, 7-Dione," in AIP Conf. Proc., vol. 2394, no. 1, p. 040019, AIP Publishing LLC, Nov. 2022.
M. A. Toma, D. A. Ibrahim, A. H. Dalaf, S. Q. Abdullah, M. M. Aftan, and E. Q. Abdullah, "Study the Adsorption of Cyclopentanone on to Natural Polymers," in AIP Conf. Proc., vol. 2394, no. 1, p. 040007, AIP Publishing LLC, Nov. 2022.
A. M. Hamad, Q. M. Atiyea, D. N. A. Hameed, and A. H. Dalaf, "Green Synthesis of Copper Nanoparticles Using Strawberry Leaves and Study of Properties, Anti-Cancer Action, and Activity Against Bacteria Isolated from Covid-19 Patients," Karbala Int. J. Mod. Sci., vol. 9, no. 1, pp. 12, 2023.
S. Jassim, A. H. Dalaf, and T. F. Abdullah, "Studying the Biological Activity and Properties of Copper Nanoparticles Prepared by Pulsed Laser Ablation in Liquid," The 3rd Int. and 5th Sci. Conf. for College of Science – Tikrit University, vol. 1, no. 25, pp. 213-221, 2022.
M. Hamad, Q. M. Atiyea, W. A. Jwair, A. H. Dalaf, A. S. Jasim, S. M. El-Saigher, Z. H. Saad, and L. J. Mohammed, "In Vitro Comparison of the Effect of Zinc Oxide Nanoparticles and Hibiscus sabdariffa Extract on Streptococcus mutans Isolated from Human Dental Caries," The 3rd Int. and 5th Sci. Conf. for College of Science – Tikrit University, vol. 2, no. 02, pp. 213-221, 2022.
S. M. Abdulkareem, R. M. Alsaffar, G. H. A. Razzaq, J. H. Mohammed, T. M. Awad, M. A. Alheety, and S. Ghotekar, "Effect of Direct and Indirect In-Situ Sonochemical Synthesis Methods of MWCNTs–CoNiFerrite on the Hydrogen Storage," J. Sol-Gel Sci. Technol., pp. 1-10, 2024.
M. J. Saleh, J. N. Saleh, K. Al-Badrany, A. W. A. S. Talluh, Q. A. Shannak, and A. Z. Abdulmajeed, "Use of Solid Basic Catalysts in the Preparation of Cyclohexenone Derivatives and Evaluation of Their Bacterial Activity," Vital Annex: Int. J. Novel Res. Adv. Sci., vol. 3, no. 3, pp. 104-112, 2024.
M. M. Aftan, H. K. Salih, and A. A. Talloh, "Synthesis of New Mesogenic Schiff Bases Ether with Polar Halogen Substituent and Study Their Liquid Crystalline Properties," J. Educ. Sci. Stud., vol. 5, no. 17, 2021.
A. S. T. Abdul Wahed, "Preparation and Evaluation of Bacterial Activity and Study of the Crystalline Properties of Some 1, 3-Oxazepine-4, 7-Dione Derivatives," Cent. Asian J. Theor. Appl. Sci., vol. 5, no. 2, pp. 15-26, 2024.
H. Dalaf, "3-Phenylimidazolidin-4-One: Characterization, Green Synthesis, Evaluation of Biological and Laser Performance," Eur. J. Mod. Med. Pract., vol. 4, no. 7, pp. 417-427, 2024.
W. A. S. Talluh, M. J. Saleh, J. N. Saleh, and H. M. S. Al-Jubori, "Synthesis and Characterization of Some New Imine Graphene Derivatives and Evaluation of Their Biological Activity," Cent. Asian J. Med. Nat. Sci., vol. 5, no. 4, pp. 272-290, 2024.
R. H. Saleh, W. M. Rashid, A. H. Dalaf, K. A. Al-Badrany, and O. A. Mohammed, "Synthesis of Some New Thiazolidinone Compounds Derived from Schiff Bases Compounds and Evaluation of Their Laser and Biological Efficacy," Ann. Trop. Public Health, vol. 23, no. 7, pp. 1012-1031, 2020.
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2024 Adil Hussein Dalaf, Mohammed Jwher Saleh, Jamil Nadhem Saleh
This work is licensed under a Creative Commons Attribution 4.0 International License.