The Synthesis of N, N´-Propylene Bis-Benzohydroxamamide Ligands and Coordination with Copper(II) Ions
Article Sidebar
Main Article Content
Abstract
In this research, the synthesis of tetradentate ligand from benzohydroxamamide bidentate ligand was developed by using a simple two-step protocol. Firstly, Benzaldoxime was converted to benzaldehyde hydroximinoyl chloride. Then, Benzaldehyde hydroximinoyl chloride was reacted with 1,3-propylenediamine to obtain the tetradentate ligand. This ligand consisted of two units of benzohydroxamamide connecting by propylene. The overall yield of a tetradentate ligand was 65.01 percents. The coordination compound of this ligand with copper (II) ion was characterized by UV-Visible spectroscopy, Infrared spectroscopy, and Mass spectroscopy. It was found that the metal to ligand ratio was 1:1. The developed method was applied to prepare ligands containing derivative of benzohydroxamamide, and the ligands can be used as food supplement or medical use.
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
The author has the sole responsibility for the material published in RTNA Journal of Science and Technology, which the editorial board may not agree on that material.
RTNA Journal of Science and Technology owns the copyright of the text, the illustration, or other material published in the journal. No parts or the whole of the material published may be disseminated or used in any form without first obtaining written permission from the academy.
References
Bost M, Houdart S, Oberli M, Kalonji E, Huneau, J, Margaritis I. Dietary copper and human health: Current evidence and unresolved issues. J Trace Elem Med Biol. 2016 May;35:107–15.
Klevay LM. Alzheimer’s disease as copper deficiency. Med Hypotheses. 2008;70(4):802–7.
Siddiqui K. Bawazeer N. Scaria SJ. Variation in Macro and Trace Elements in Progression of Type 2 Diabetes. The Scientific World Journal. 2014 Aug 5:1–9.
Kim JJ, Kim YS, Kumar V. Heavy metal toxicity: an update of chelating therapeutic strategies. J Trace Elem Med Biol. 2019 Jul;54:226-31.
Eloy F, Lenaers R. The Chemistry of Amidoximes and Related Compounds. Chem Rev. 1962 Apr 1;62(2):155–183.
Clement B. Reduction of N-hydroxylated compounds: Amidoximes (N-hydroxyamidines) as pro-drugs of amidines. Drug Metlab Rev. 2002 Aug;34(3):565-79.
Clement B, Christiansen K, Girreser U. Phase 2 Metabolites of N-Hydroxylated Amidines (Amidoximes): Synthesis, in Vitro Formation by Pig Hepatocytes, and Mutagenicity Testing. Chem Res Toxicol. 2001 Mar;14(3):319-26.
Fylaktakidou KC, Hadjipavlou LDJ, Litinas KE, Varella EA, Nicolaides DN. Recent Developments in the Chemistry and in the Biological Applications of Amidoximes. Curr Pharm Des. 2008;14(10):1001-47.
Bolotin DS, Bokach NA, Kukushkin VY. Coordination chemistry and metal-involving reactions of amidoximes: Relevance to the chemistry of oximes and oxime ligands. Coord Chem Rev. 2015 Nov;313:62–93.
Witte EG, Schwochau KS, Henkel G. Krebs B. Uranyl complexes of acetamidoxime and benzamidoxime. Preparation, characterization, and crystal structure. Inorganica Chimica Acta, 1984 Jun;94(6):323–31.
Nakayama M, Xu LC, Koga Y, Harada K, Sugii A, Nakayama H, Okabayashi I. Hydroxamamide as a chelating moiety for the preparation of 99mTc-radiopharmaceuticals III. Characterization of various 99mTc-hydroxamamides. Appl Radiat Isot. 1997 May;48(5):571–7.
Xu LC, Nakayama M, Harada K, Nakayama H, Tomiguchi S, Kojima A, Arano Y. Synthesis and Evaluation of Hydroxamamide-Based Tetradentate Ligands as a New Class of Thiol-Free Chelating Molecules for 99mTc Radiopharmaceuticals. Nucl Med Biol. 1998 Apr;25(3):295-303.
Mccarroll A, Walton JC. Exploitation of aldoxime esters as radical precursors in preparative and EPR spectroscopic roles. J Chem Soc Perkin 1. 2000 Dec;2(12):2399–2409.
Gennet D, Zard SZ, Zhang H. Amidinyl radicals: new and useful intermediates for the synthesis of imidazolines and imidazoles. Chem Commun (Camb). 2003 Aug 7;(15):1870-1.
Kumar V, Kaushik MP. A novel one-pot synthesis of hydroximoyl chlorides and 2-isoxazolines using N-tert-butyl-N-chlorocyanamide. Tetrahedron Lett. 2006 Feb 27; 47(9):1457–60.
Shang Y, Hu M, He X, Niu Z, Yan Z, Zhou F. Synthesis of 3,4,5-Trisubstituted Isoxazoles by the 1,3-Dipolar Cycloaddition Reaction of α-Azido Acrylates and Aromatic Oximes. Synthesis. 2014;46(04):510–4.
Nishida Y, Kida S. A Study of Electronic Spectra of Square Planar Copper(II) and Nickel(II) Complexes by Circular Dichroism. Bull Chem Soc Jpn. 1970:43(12):3814–9.