Derivatization of valproic acid using ferrocene derivatives: Synthesis, characterization and investigation of optical and electrochemical properties
Corresponding Author
Keshvar Rahimpour
Pharmaceutical Analysis Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran
Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran
Correspondence
Keshvar Rahimpour, Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran.
Email: [email protected]
Search for more papers by this authorAbolghasem Jouyban
Pharmaceutical Analysis Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran
Search for more papers by this authorReza Teimuri-Mofrad
Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran
Search for more papers by this authorCorresponding Author
Keshvar Rahimpour
Pharmaceutical Analysis Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran
Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran
Correspondence
Keshvar Rahimpour, Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran.
Email: [email protected]
Search for more papers by this authorAbolghasem Jouyban
Pharmaceutical Analysis Research Center and Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran
Search for more papers by this authorReza Teimuri-Mofrad
Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran
Search for more papers by this authorAbstract
New ferrocenyl-based valproic acid (VPA) ester derivatives were designed and synthesized according to the reaction of appropriate haloalkylferrocene derivatives with VPA in the presence of K2CO3 and a catalytic amount of 18-crown-6 ether. Elemental analyses and Fourier transform infrared, 1H NMR, 13C NMR and mass spectra all well confirmed the predicted molecular structure. This is the first report in which ferrocene has been applied in derivatization of VPA as a chromogenic group. The electrochemical properties of the synthesized compounds were studied using cyclic voltammetry measurements, and energies of the frontier molecular orbitals were determined. In addition, the solubilities of the final compounds were studied in distilled water, phosphate buffer (pH = 7.4) and 0.9% (w/v) NaCl solution.
Supporting Information
| Filename | Description |
|---|---|
| aoc5007-sup-0001-Supporting_Information.docxWord 2007 document , 1.7 MB |
Figure S1. NMR spectra of 2-ferrocenylethyl 2-propylpentanoate (VPAC2Fc, 6a). H NMR (CDCl3, 400 MHz) Figure S2. NMR spectra of 3-ferrocenylpropyl 2-propylpentanoate (VPAC3Fc, 6b). 1H NMR (CDCl3, 400 MHz) Figure S3. NMR spectra of 4-ferrocenylbutyl 2-propylpentanoate (VPAC4Fc, 6c). 1H NMR (CDCl3, 400 MHz) Figure S4. NMR spectra of 2-oxo-2-ferrocenylethyl 2-propylpentanoate (VPACOFc, 6d). 1H NMR (CDCl3, 400 MHz) |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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