Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity

Palion-Gazda, Joanna; Luz, André; Raposo, Luís R.; Choroba, Katarzyna; Nycz, Jacek E.; Bieńko, Alina; Lewińska, Agnieszka; Erfurt, Karol; Baptista, Pedro V.; Fernandes, Alexandra R.; Shul’pina, Lidia S.; Ikonnikov, Nikolay S.; Shul’pin, Georgiy B.

doi:10.3390/molecules26216364

Cited by 8 publications

(6 citation statements)

References 109 publications

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“…Oxovanadium(IV) complexes are a class of organometallic compounds that have characteristic structure where an oxygen atom is bonded to vanadium atom by a double bond at the apical position of the molecule. Due to prominent efficacy of this group towards screening against different disease-causing agents, the coordination complexes containing this moiety has garnered augmented interest in the field of biological chemistry and medicinal chemistry [1]. Although many other medicinal properties of vanadium complexes like the insulin mimetic property have been studied extensively in the past decades, its complexes with Schiff bases were not able to underscore their effectiveness in the treatment of other different types of diseases.…”

Section: Introductionmentioning

confidence: 99%

Chemical Synthesis, Characterization, and Computational Investigation of Two Schiff Bases Derived From 3-(2-Hydroxyphenyl)-4-amino-4H-1,2,4-triazole-5- thiol and Their Corresponding Oxovanadium(IV) Complexes

Sharma

Subin²,

Panthi

et al. 2023

J. Nepal Chem. Soc.

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A triazole, 2-(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)phenol, has been prepared from 2-hydroxybenzoic acid by routine multi-step chemical synthesis. It was then used in synthesizing two different Schiff base ligands (L1 and L2). Their respective oxovanadium (IV) complexes (ML1 and ML2) were consequently synthesized and characterized by different experimental techniques like elemental analysis, FTIR spectroscopy, UV-Visible spectroscopy, and EPR spectrometry. The cyclic voltammetry measurements showed the electrochemically stable nature of the complexes. The powder X-ray diffraction patterns revealed the presence of monoclinic crystals with particle sizes of ca. 15-17 nm for both complexes. DFT calculations were performed for the determination of geometrical models, energetic stability, electronic properties, spectral features, and reactivity of the synthesized ligands and complexes. The spectral characterization of the complexes suggests a square-pyramidal geometry around VO (IV)group and was supported by computational results derived from the proposed models. This work shows that computational calculation along with experimental characterization provides better insights into new chemical compounds and their properties that could be performed in parallel as a regular tool.

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Section: Introductionmentioning

confidence: 99%

Chemical Synthesis, Characterization, and Computational Investigation of Two Schiff Bases Derived From 3-(2-Hydroxyphenyl)-4-amino-4H-1,2,4-triazole-5- thiol and Their Corresponding Oxovanadium(IV) Complexes

Sharma

Subin²,

Panthi

et al. 2023

J. Nepal Chem. Soc.

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“…The metal ion is also relevant for the carboxylate complex, since different metals lead to distinct applications in catalysis, or as a sensor, pigment, etc. In particular, vanadium metal is very interesting due to its variability of oxidation states (+5, +4, +3, +2, and +1) allowing different forms of bonding, which can influence the structural characteristics for catalytic, microbiological, and even medicinal applications [ 8 , 9 , 10 , 11 , 12 ]. An impasse in the use of vanadium is its toxicity, some studies point out that the metal is essential in small amounts and toxic in excess [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Eco-Friendly Synthesis of an Oxovanadium(IV)-bis(abietate) Complex with Antimicrobial Action

et al. 2022

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The search for less expensive and viable products is always one of the challenges for research development. Commonly, the synthesis of coordination compounds involves expensive ligands, through expensive and low-yield routes, in addition to generating toxic and unusable residues. In this work, the organic ligand used is derived from the resin of a reforestation tree, Pinus elliottii var. elliottii. The synthesis method used Pinus resin and an aqueous solution of vanadium(III) chloride at a temperature of 80 °C. The procedure does not involve organic solvents and does not generate toxic residues, thus imparting the complex formation reaction a green chemistry character. The synthesis resulted in an unprecedented oxovanadium(IV)-bis(abietate) complex, which was characterized by mass spectrometry (MS), chemical analysis (CHN), vibrational (FTIR) and electronic spectra (VISIBLE), X-ray diffraction (XRD), and thermal analysis (TG/DTA). Colorimetric studies were performed according to the CIELAB color space. The structural formula found, consisted of a complex containing two abietate ligands, [VO(C20H29O2)2]. The VO(IV)-bis(abietate) complex was applied against microorganisms and showed promising results in antibacterial and antifungal activity. The best result of inhibitory action was against the strains of Gram-positive bacteria S. aureus and L. monocytogenes, with minimum inhibitory concentration (MIC) values of 62.5 and 125 μmol L−1, respectively. For Gram-negative strains the results were 500 μmol L−1 for E. coli; and 1000 μmol L−1 for Salmonella enterica Typhimurium. Antifungal activity was performed against Candida albicans, where the MIC was 15.62 μmol L−1, and for C. tropicalis it was 62.5 μmol L−1. According to the MFC analysis, the complex presented, in addition to the fungistatic action, a fungicidal action, as there was no growth of fungi on the plates tested. The results found for the tests demonstrate that the VO(IV)-bis(abietate) complex has great potential as an antimicrobial and mainly antifungal agent. In this way, the pigmented ink with antimicrobial activity could be used in environments with a potential risk of contamination, preventing the spread of microorganisms harmful to health.

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“…The second original research article (by Joanna Palion-Gazda, André Luz, Luis R. Raposo, Katarzyna Choroba, Jacek E. Nycz, Alina Bie ńko, Agnieszka Lewi ńska, Karol Erfurt, Pedro V. Baptista, Barbara Machura, Alexandra R. Fernandes, Lidia S. Shul'pina, Nikolay S. Ikonnikov, and Georgiy B. Shul'pin) reports on the use of methyl-substituted 8hydroxyquinolines (Hquin) for the preparation of five-coordinated oxovanadium(IV) complexes [VO(2,6-(Me) 2 -quin) 2 , VO(2,5-(Me) 2 -quin) 2 , and VO(2-Me-quin) 2 ]. These complexes were then used as catalysts for the efficient oxidation of hydrocarbons (to alcohols) and alcohols (to ketones), carried out with H 2 O 2 in acetonitrile at 50 • C in the presence of 2-pyrazinecarboxylic acid (PCA) as a cocatalyst [5].…”

mentioning

confidence: 99%

“…The subsequent papers report on transition-metal-promoted cyclization processes leading to heterocyclic derivatives. Thus, new polycyclic heterocycles (1H-benzo [4,5]imidazo[1,2c][1,3]oxazin-1-ones) were synthesized by Lucia Veltri, Roberta Amuso, Marzia Petrilli, Corrado Cuocci, Maria A. Chiacchio, Paola Vitale, and Bartolo Gabriele using a ZnCl 2promoted deprotective annulation approach starting from N-Boc-2-alkynylbenzimidazoles under mild conditions (CH 2 Cl 2 as the solvent at 40 • C for 3 h) [6]. N-benzoylindoles were obtained by Zhe Chang, Tong Ma, Yu Zhang, Zheng Dong, Heng Zhao, and Depeng Zhao by Pd(II)-catalyzed oxidative C-H functionalization and annulation of substituted N-(2allylphenyl)benzamides, carried out with Pd(OAc) 2 as the catalyst in the presence of benzoquinone as the oxidant and dibutyl phosphate as the additive in DMSO at 60-70 • C [7].…”

mentioning

confidence: 99%

Organic Synthesis via Transition Metal-Catalysis

Gabriele

2022

Molecules

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Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity

Cited by 8 publications

References 109 publications

Chemical Synthesis, Characterization, and Computational Investigation of Two Schiff Bases Derived From 3-(2-Hydroxyphenyl)-4-amino-4H-1,2,4-triazole-5- thiol and Their Corresponding Oxovanadium(IV) Complexes

Chemical Synthesis, Characterization, and Computational Investigation of Two Schiff Bases Derived From 3-(2-Hydroxyphenyl)-4-amino-4H-1,2,4-triazole-5- thiol and Their Corresponding Oxovanadium(IV) Complexes

Eco-Friendly Synthesis of an Oxovanadium(IV)-bis(abietate) Complex with Antimicrobial Action

Organic Synthesis via Transition Metal-Catalysis

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