Synthesis and characterization of novel bis(diphenylphosphino)-oxalyl and (substituted) malonyl dihydrazones: P,N,N,P-tetradentate complexes of an oxalyl derivative with Cu(II), Pd(II), and Mn(II)

Adam, Mohamed Shaker S.; Mohamad, Ahmad Desoky M.; Elhady, Omar M.

doi:10.1007/s00706-013-1122-4

Cited by 12 publications

(6 citation statements)

References 65 publications

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“…The molar ratio [14,15,16] and continuous variation methods [19] were applied to determine the equilibria in its solutions and to evaluate the ratio of metal ion to the coordinated ligands, as M : L ratio.…”

Section: Stoichiometry Evaluation and Apparent Formation Constantsmentioning

confidence: 99%

“…Formation constant values (K f ) of Cr(III)-imine complexes, which are investigated in solutions, are derived from the spectrophotometric measurements with operating of the continuous variation method [14,15,16] as follows:…”

Section: Stoichiometry Evaluation and Apparent Formation Constantsmentioning

confidence: 99%

“…Several studies have been reported that the oxo-chromium(V) complexes are probably the intermediates in the oxidation processes of various organic compounds catalyzed by Cr III complexes [38,39,40,41,42]. Hence, the Cr V − −O active species are formed through the oxygen transfer mechanism from the coordinated oxidant molecule to give the active intermediate (structure III) with extraction of a water molecule [14]. The change in the color of the reaction in the beginning of the catalytic oxidation process initial solution from light green to brown highly supports the suggestion for the oxygen transfer from the oxidant (H 2 O 2 ) to the central metal ion (Cr V ) to form oxo-chromium(V) species (structure III in the mechanistic proposal).…”

Section: Proposed Catalytic Mechanismmentioning

confidence: 99%

“…Transition metal complexes with imine ligands as Schiff base derivatives [13] are cataloged as the backbone of the catalysts for the oxidation of alcohols, thioles, thiophenes, and olefins due to their commercially cheap, easy preparation and specific chemical and thermal stability in both solid and liquid phases [14,15,16]. In addition, another component of our catalytic system is the oxidant, that is, H 2 O 2 , which is widely used and applied for being a clean and inexpensive oxidant.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H₂O₂

Abdel‐Rahman¹,

Adam²,

Abu‐Dief³

et al. 2019

J Trans Met Compl

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Chromium(III) complexes were derived, as tri-and tetradentate imine chelates, from 2-hydroxy-1-napthaldehyde or 3ethoxysalicylaldehyde with 2-aminophenol or 1,2-phenylenediamine. The catalytic potentials of Cr(III)-imine chelates were probed and tested in the chemoselective benzyl alcohol oxidation to benzaldehyde (BA) within an eco-friendly terminal oxidant (i.e., H 2 O 2 ). The effect of various applicable parameters in the catalytic systems (e.g., solvents, temperature, and catalyst molar ratios) was studied. From the obtained results, it is found that the most favored and suitable solvent applied is acetonitrile at best reaction conditions; temperature 80 °C after 4 h. The mechanistic aspects of the Cr(III)-catalyzed oxidation were tentatively described and discussed based on electron and oxygen transfer processes.

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Section: Stoichiometry Evaluation and Apparent Formation Constantsmentioning

confidence: 99%

Section: Stoichiometry Evaluation and Apparent Formation Constantsmentioning

confidence: 99%

Section: Proposed Catalytic Mechanismmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H₂O₂

Abdel‐Rahman¹,

Adam²,

Abu‐Dief³

et al. 2019

J Trans Met Compl

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“…Hemi-synthetic hydrazones issued from natural ketones and aldehydes can be further converted to their corresponding alkane via the Wolff-Kishner Reduction method [27] . Besides, the di-Schiff bases are polyfunctional N,O,O,N-type ligands which may form mono-, di-, and polynuclear complexes with monoterpene ketones [ 26 , 28 ] involving ligand bridging and oxobridging [29] . Thus, the possible C = N imine condensation provided by hemi-synthesis processes may eventually allow access to more potent molecules that may exhibit a promising in vivo pharmacokinetic profile and other desirable biological properties.…”

Section: Introductionmentioning

confidence: 99%

Hemi-synthesis of novel (S)-carvone hydrazone from Carum carvi L. essential oils: Structural and crystal characterization, targeted bioassays and molecular docking on human protein kinase (CK2) and Epidermal Growth factor Kinase (EGFK)

Tedjini

Ziani

Casimiro

et al. 2021

Journal of Molecular Structure

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Polyfunctional N,O,O,N-type ligands such as the oxalyl dihydrazide (ODH) may induce formation of mono-, di-, and polynuclear complexes with natural monoterpene ketones, involving ligand bridging and Oxobridging. In this context, a novel chiral dihydrazone is designed through hemi-synthesis process by reacting oxalyldihydrazide (ODH) with ( s )-carvone, the major compound of caraway's seeds essential oil. The C = N imine bi-condensation is performed without prior isolation of the natural ( s )-carvone and the resulting ( s )-carvone dihydrazone (s-CHD) is structurally characterized by Single-crystal X-ray diffraction, 2D-NMR spectroscopy and chiral LCMS analysis to confirm the formation of a single pure enantiomer. In -vitro cell-based assays were conducted on normal fibroblast (L929) using a presBlue (PB) fluorescence quantification method of cell-viability and by sulforhodamine B calorimetric cytotoxicity assays to determine the anti-proliferative effect on four human tumoral lines (NCI-H460, Hela, HepG2 and MCF-7) and normal PLP2. Anti-inflammatory assays were determined through NO production by Maurine LPS-stimulated macrophages (RAW 264.7). The ( s )-CHD has no effect on normal cells viability ( > 88%) and PLP2 (GI50 = 326 ug/mL), while a moderate ( ∼55%) to significant ( ∼63%) antigrowth potential was recorded against HepG2, Hela and MCF-7 tumor cell lines, where RAW 264.7 was feebly sensitive. A molecular docking was performed using Autodock vina software on the protein kinase CK2 and Epidermal Growth factor Kinase proteins EGFK and the dock scores allowed to identify significant binding affinities (lower G and Ki values) and potential hydrophilic/hydrophobic interactions with ( s )-CHD comparing to the clinical ellipticine as potential ligands. Molecular docking suggests that ( s )-CHD possesses high affinity towards the kinase domain receptors CK2 and EGFR, being able to bind to the ATP region.

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Bis‐dioxomolybdenum (VI) oxalyldihydrazone complexes: Synthesis, characterization, DFT studies, catalytic epoxidation potential, molecular modeling and biological evaluations

Adam

Ahmed

Elhady

et al. 2020

Applied Organom Chemis

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Two cis‐bis‐dioxomolybdenum oxalylsalicylidenedihydrazone complexes (MoO2L1 and MoO2L2) were synthesized via the complexation of dioxomolybdenum (VI) acetylacetonate with oxalylsalicylidenedihydrazone (H2L1) and p‐sodium sulfonate oxalylsalicylidenedihydrazone (H2L2) bis‐Schiff base chelating ligands, respectively. The structures of the newly synthesized complexes were confirmed by 1H‐ and 13C‐NMR, IR, ultraviolet–visible and mass spectra, as well as elemental analyses (EA) and conductivity measurements. The spectrophotometric continuous variation method revealed the formation of 2: 1 (metal: ligand molar ratios). DFT studies were applied for the ligands and their Mo‐chelates. Interestingly, the bis‐MoO2(VI) oxalyldihydrazone complexes showed remarkable catalytic sufficiency towards the selective (ep)oxidation of 1,2‐cyclooctene, benzyl alcohol and thiophene using H2O2 or tert‐butyl hydroperoxide (tBuOOH) at 85 °C. Under aqueous conditions, the MoO2L2 (with p‐sodium sulfonate substituent) exhibited superior that of the MoO2L1 (without p‐NaSO3―group), highlighting the role of sodium sulfonate substituent in the catalytic progress of the Mo‐chelate. The ligands (H2L1 and H2L2) and their corresponding Mo‐complexes (MoO2L1 and MoO2L2) were assessed for their antitumor and antimicrobial activities. Furthermore, the antioxidant activity was also evaluated using the 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and superoxide dismutase (SOD) assays. The binding nature between the Mo‐complexes and calf thymus DNA (ctDNA) was also studied within spectroscopic and hydrodynamic techniques.

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Synthesis and characterization of novel bis(diphenylphosphino)-oxalyl and (substituted) malonyl dihydrazones: P,N,N,P-tetradentate complexes of an oxalyl derivative with Cu(II), Pd(II), and Mn(II)

Cited by 12 publications

References 65 publications

Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H₂O₂

Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H₂O₂

Hemi-synthesis of novel (S)-carvone hydrazone from Carum carvi L. essential oils: Structural and crystal characterization, targeted bioassays and molecular docking on human protein kinase (CK2) and Epidermal Growth factor Kinase (EGFK)

Bis‐dioxomolybdenum (VI) oxalyldihydrazone complexes: Synthesis, characterization, DFT studies, catalytic epoxidation potential, molecular modeling and biological evaluations

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Synthesis and characterization of novel bis(diphenylphosphino)-oxalyl and (substituted) malonyl dihydrazones: P,N,N,P-tetradentate complexes of an oxalyl derivative with Cu(II), Pd(II), and Mn(II)

Cited by 12 publications

References 65 publications

Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H2O2

Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H2O2

Hemi-synthesis of novel (S)-carvone hydrazone from Carum carvi L. essential oils: Structural and crystal characterization, targeted bioassays and molecular docking on human protein kinase (CK2) and Epidermal Growth factor Kinase (EGFK)

Bis‐dioxomolybdenum (VI) oxalyldihydrazone complexes: Synthesis, characterization, DFT studies, catalytic epoxidation potential, molecular modeling and biological evaluations

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Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H₂O₂

Catalytic Potential of Mononuclear Cr(III)-Imine Complexes for Selective Oxidation of Benzyl Alcohol by Aqueous H₂O₂