Author(s): Huda Jamal Al-Adhami, Suaad M. H. Al-Majidi, Thikra Hasan Mathkor

Email(s): huda1.aladhami@gmail.com

DOI: 10.5958/0974-360X.2020.00930.0   

Address: Huda Jamal Al-Adhami*, Suaad M. H. Al-Majidi, Thikra Hasan Mathkor
1Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq.
*Corresponding Author

Published In:   Volume - 13,      Issue - 11,     Year - 2020


ABSTRACT:
In this work the synthesis of a 6-( amino acetyl chloride)-1,3-dimethylpyrimidine-2,4-dione-6-yl [1] by reaction of 6-amino-1,3-dimethyluracil with chloroacetyl chloride, triethylamine in DMF as a solvent, the product [1] then, reacted with a hydrazine hydrate in absolute ethanol to produce hydrazide derivative [2]. A series of Schiff bases (3-8) were synthesized in moderate yields via a reaction of 6-(hydrazinoacetamide)-1,3-dimethyl pyrimidine-2,4-dione-6-yl [2], substituted aryl aldehydes and glacial acetic acid under reflux conditions. The resulting [3-8] could be useful for the synthesis of [9-26] ß-Lactams derivatives. They have been achieved by cyclization of Schiff bases compounds with different reagents (chloroacetyl chloride, phenyl isocyanate and phenyl isothiocyanate) in THF solvent. All newly synthesized compounds conformation were characterized in detail by FT-IR and NMR spectroscopy including 1D NMR experiments (1H and 13C). The study antioxidant of some new compounds.


Cite this article:
Huda Jamal Al-Adhami, Suaad M. H. Al-Majidi, Thikra Hasan Mathkor. Synthesis and Identification of some new β-Lactam derivatives from 6-amino-1,3-dimethyluracil and study their antioxidant activity. Research J. Pharm. and Tech. 2020; 13(11):5317-5327. doi: 10.5958/0974-360X.2020.00930.0


REFERENCES:
1.    Jiang KU, Yi JI and Jun LI. 1, 3-Dipolar Cycloaddition of Uracil Derivatives with Nitrile Oxides: Synthesis of [1, 2, 4] Oxadiazolo [4, 5-C] Pyrimidine-5, 7 (6h)-Dione Derivatives." Tetrahedron. 2017;  73(47): 6662-6668.
2.    Gkotsos GE, Christina VI, Ioanna LA, Chrysanthi SA, Nikolaos RA, Georgios TH and Georgios DI. The Role of Sarcosine, Uracil, and Kynurenic Acid Metabolism in Urine for Diagnosis and Progression Monitoring of Prostate Cancer." Metabolites. 2017; 7(1): 1-9.
3.    Pałasz AL and Dariusz CI. In Search of Uracil Derivatives as Bioactive Agents. Uracils and Fused Uracils: Synthesis, Biological Activity and Applications." European Journal of Medicinal Chemistry. 2015; 97: 582-611.
4.    Kostova IR and Petar YA. Antioxidant Properties of Pyrimidine and Uracil Derivatives." Current Organic Chemistry. 2017; 21(20): 2096-2108.
5.    Sorní CA, Mari LU, Moreno SA, María MI, María IN, Antonio FA, María AN, Navarro MO, Santos FU, Salvador ME and Vicente VI. Antioxidant Capacity of 5-Fluorouracile and New Fluorinated Uracil Derivates." Nereis: revista iberoamericana interdisciplinar de métodos, modelización y simulación. 2018; 10: 99-105.
6.    Zhao SH, Ke LI, Yi JI and Jun LI. Synthesis and Biological Evaluation of Novel 1-(Aryl-Aldehyde-Oxime) Uracil Derivatives as a New Class of Thymidine Phosphorylase Inhibitors." European Journal of Medicinal Chemistry. 2018; 144: 41-51.
7.    Alper TU, Murat ŞE, Claudiu SU and Deniz EK. Carbonic Anhydrase Inhibitory Properties of Some Uracil Derivatives." Journal of Enzyme Inhibition and Medicinal Chemistry. 2017; 32(1): 74-77.
8.    Paramonova MA, Anastasia KH, Katherine SE and Mikhail NO. Mendeleev Commun. 2017; 27: 85-87.
9.    Putz MI, Nicoleta DU and Adriana IS. Double Variational Binding—(Smiles) Conformational Analysis by Docking Mechanisms for Anti-HIV Pyrimidine Ligands." International Journal of Molecular Sciences. 2015; 16(8): 19553-19601.
10.     Zou JU, Ling WU, Zheng MI, Ping ZH, Zuo HO. Determination of the Main Nucleosides and Nucleobases in Natural and Cultured Ophiocordyceps Xuefengensis." Molecules. 2017; 22(9) 1530.
11.     Kim SE, Minhee LE, So YO, Soo MI, Eun JE, Jae SU, Jihyae AN, Jiyoun LE, and Jeewoo LE. Synthesis and Biological Evaluation of 3-(2-Aminoethyl) Uracil Derivatives as Gonadotropin-Releasing Hormone (Gnrh) Receptor Antagonists." European Journal of Medicinal Chemistry. 2018; 145: 413-424.
12.    Kozanecka OK, Weroni KA, Beata JA, Tomasz PO, Renata JA, Monika SK and Lucyna MR. Spectroscopy, Molecular Modeling and Anti-Oxidant Activity Studies on Novel Conjugates Containing Indole and Uracil Moiety." Journal of Molecular Structure. 2018; 1169: 130-137.
13.    Stecko SE, Bartłomiej FU and Marek CH. Kinugasa Reaction: An Ugly Duckling of-Lactam Chemistry." Tetrahedron 70 (2014): 7817-7844.
14.    Abrams EL, Adelle AT, Tiffany WO and Moshe BE. The Importance of Delabeling Β-Lactam Allergy in Children." The Journal of Pediatrics. 2019; 204: 291-297.
15.    Timm AL, Ewa BO, Marius MA, Sylvain ME, Christian ZW, Stefan BR and Harald HO. Photolysis of Four Β Lactam Antibiotics under Simulated Environmental Conditions: Degradation, Transformation Products and Antibacterial Activity." Science of The Total Environment. 2019; 651: 1605-1612.
16.    Zagursky RO and Michael PI. Cross-Reactivity in Β-Lactam Allergy. The Journal of Allergy and Clinical Immunology: In Practice. 2018; 6(1) 72-81.
17.    Tayari MA, Zahra MO, Fatemeh MO, Mostafa RE, and Marzieh. Heterotropic Effect of Β-Lactam Antibiotics on Antioxidant Property of Haptoglobin (2-2)-Hemoglobin Complex." Iranian Journal of Pharmaceutical Research. 2011; 10(2) 313.
18.    Shahani SO, Farzaneh BE, Danial JA, Maryam GH and Fatemeh SH. Antioxidant and Anti-Inflammatory Effects of Nasturtium Officinale Involved in Attenuation of Gentamicin-Induced Nephrotoxicity." Toxicology Mechanisms and Methods. 2017; 27(2) 104-107.
19.    Hussein AB, Mohammed GH, Khaled MA and Osama AB. Beta Lactams Antibiotic Ceftriaxone Modulates Seizures, Oxidative Stress and Connexin 43 Expression in Hippocampus of Pentylenetetrazole Kindled Rats." Journal of Epilepsy Research. 2016; 6(1): 1-8.
20.    Zeynep C, Senem A and Zulbiye K. Reaction of aminopyrimidine derivatives with chloroacetyl chloride and isopthaloyl chloride.
21.    Suaad MH, Hala AR, Suhad FA. Synthesis, Identification and Evaluation of Antimicrobial Activities of some New N-substituted 2-azetidinone, Imidazolidinone and tetrazole derivatives of 2-(methylthio) benzimidazole " International Journal of Science and Research. 2015; 6(1): 2319-7064.
22.    Safa T and Hasan G. Synthesis and characterization of β-Lactam compounds" JPOCR. 2016; 8(8): 730-738.
23.    Ahmed WN and Atheer MM. Synthesis and Characterization of Heterocyclic Derivatives Containing Four, Five, Six and Seven Membered Rings from 6-Methyl 2-Thiouracil and Evaluation their Biological Activity.2015.
24.    Das M, Das B and Samanta A. Antioxidant and anticancer activity of synthesized 4‐amino‐5‐((aryl substituted)‐4H‐1, 2, 4‐triazole‐3‐yl) thio‐linked hydroxamic acid derivatives. Journal of Pharmacy and Pharmacology. 2019.
25.    Philip S, Jayasree EG and Mohanan K. Antidiabetic, antioxidant, DFT and molecular docking studies of a triazene derivative and its transition metal complexes. Research on Chemical Intermediates. 2019; 1-25.
26.    Verma G. A Review Exploring Therapeutic Worth of 1, 3, 4-Oxadiazole Tailored Compounds. Mini Reviews in Medicinal Chemistry. 2019; 19(6): 477-509.
27.    Krishna S. GCMS analysis, antioxidant and antibacterial activities of ethanol extract of Anisomeles malabarica (L.) R. Br. ex. Sims leaves. Asian Journal of Pharmacy and Pharmacology. 2019; 5(1): 180-187.
28.    Haida Z and Hakiman M. A comprehensive review on the determination of enzymatic assay and nonenzymatic antioxidant activities. Food Science & Nutrition. 2019; 7(5): 1555-1563.
29.    Redhab A and Suaad MH. Synthesis, Characterization and Evaluation of Antimicrobial Activity for New Heterocyclic Derivatives Containing Pentagonal, Hexagonal Rings" Iraqi Journal of Science. 2014; 55(4): 1694-1707.
30.    Shriner R, Fuson R, Cartin D and Morril T. The systematic Identification of Organic Compounds). John Wiley and Sons, New York, USA. 1980; 8th ed.
31.    Silverstein We.  Spectrometric Identification of Organic Compounds. USA, John Wiley & Sons. 2005; 7ed.
32.    Lim S. Evaluation of antioxidant activities of various solvent extract from Sargassum serratifolium and its major antioxidant components. Food Chemistry. 2019; 278: 178-184.
33.    Cesari L, Mutelet F and Canabady L. Antioxidant properties of phenolic surrogates of lignin depolymerisation. Industrial Crops and Products. 2019; 129: 480-487.

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