Double piperazinediium and 1,4-diazabicyclo[2.2.2]octanediium MII selenates (MII=CoII, NiII, CuII, ZnII) as effective catalysts for Henry reaction

Nkhili, Nouha Loulou; Rekik, Walid; Mhiri, Tahar; Mahmudov, Kamran T.; Kopylovich, Maximilian N.; Naı̈li, Houcine

doi:10.1016/j.ica.2013.12.007

Cited by 21 publications

(3 citation statements)

References 24 publications

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“…Some nickel compounds can also act as catalysts towards the Henry reaction under different conditions, namely in homogeneous systems [23], under solvent free microwave conditions [16] or in ionic liquids [24], and high activities (more than 90% yields) are found in a few cases [16,24].…”

Section: Introductionmentioning

confidence: 99%

A new cyclic binuclear Ni(II) complex as a catalyst towards nitroaldol (Henry) reaction

Sutradhar

Silva

Pombeiro

2014

Catalysis Communications

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Section: Introductionmentioning

confidence: 99%

A new cyclic binuclear Ni(II) complex as a catalyst towards nitroaldol (Henry) reaction

Sutradhar

Silva

Pombeiro

2014

Catalysis Communications

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“…On the other hand, the supramolecular hybrid materials represent also an interesting opportunity for the development of new materials in different applications, as dielectrics, semiconductors or NLO materials [22,23]. Among them, many sulfates and selenates have been elaborated using organic molecules as templates, while cations involved in their syntheses have included transition metals [24][25][26][27][28][29][30][31], lanthanides [32] and actinides [33]. The diversity of structure framework dimensionality that could be built from chains, layers, or three dimensional connections was mentioned.…”

Section: Introductionmentioning

confidence: 99%

Structure Evolution and Thermal Decomposition of Supramolecular and Lamellar Hybrid Sulfates Templated by 4-Aminopyridinium

Hfidhi

Kammoun

Bataille

et al. 2021

J Inorg Organomet Polym

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The aromatic diamine 4-aminopirydine was used for the synthesis of a series of supramolecular metal-organic sulfate salts. The obtained compounds with the formulacrystallize with a triclinic symmetry (S.G. P1 � ). These complexes possess a hybrid structure type with an interlayer distance that varies from 10 to 12 Å depending on the metal. The fact that the crystal structure is supramolecular, the mineral layer is built from hydrogen bonds only and the interlayer space is filled with aromatic diamines that form chains through π…π interactions. The thermal study in-situ of all metal compounds revealed an important stability with the formation of crystalline phases during heating. The dehydration proceeds differently according to the metal incorporated into the structure.

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“…14 Previously, some double piperazinediium-M(II){M(II) ¼ Cu(II), Co(II), Zn(II)} sulfates were synthesized as catalysis for organic diastereoselective transformation. 15,16 Since our interest was to nd a lead metal-based antitumor drug candidate, we have therefore carried out in vitro binding studies of ionic tin(IV) iminodiacetic acid-piperazinediium conjugate (1) with multiple targets of drugs viz., DNA, RNA and topoisomerase I. Complex 1 bears structural novelty as a chemotherapeutic molecular entity possessing a dianaionic iminodiacetate trichlorotin(IV) chloride moiety that acts in synergy with the dicationic piperazinediium counter ion to undergo multiple binding interactions at the site of action selectively in cancerous tissues leaving healthy or normal cells unaffected.…”

Section: Introductionmentioning

confidence: 99%

Crystal structure determination, spectroscopic characterization and biological profile of a tailored ionic molecular entity, Sn(iv) iminodiacetic acid–piperazinediium conjugate: in vitro DNA/RNA binding studies, Topo I inhibition activity, cytotoxic and systemic toxicity studies

et al. 2015

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A novel ionic tin(IV) iminodiacetic acid-piperazinediium conjugate (1) was designed and synthesized as a potential antitumor chemotherapeutic molecular entity and was thoroughly characterized by elemental analysis, FT-IR, 1 H, 13 C and 119 Sn NMR, ESI MS and single crystal X-ray crystallography. Complex 1 resulted from the proton transfer reaction between iminodiacetic acid (H 2 IDA) and piperazine (pipz), and its subsequent complexation with tin(IV) chloride salt. 1 crystallized in orthorhombic space group Ima2 and comprises of an anionic metallic unit, a piperazinediium cation and a chloride ion. In continuity of our previous strategy in search of robust metal-based antitumor drug entities exhibiting reduced systemic toxicity, we have carried out in vitro interaction studies of 1 with ct-DNA, tRNA and Topo I targets, to validate its chemotherapeutic potential. Complex 1 exhibited more avid binding propensity with RNA which was reflected by its higher K b and K values with RNA as compared to DNA.Topoisomerase inhibition activity of 1 was performed by gel electrophoresis which revealed significant inhibitory effect on the catalytic activity of the enzyme at 30 mM concentration. Molecular docking studies of the complex were carried out with DNA (PDB ID: 1BNA), RNA (PDB ID: 6TNA) and Topo I (PDB ID: ISC7) targets to ascertain the specific binding mode thereby substantiated the spectroscopic results.Cytotoxic studies were carried out on a panel of eight human cancer cell lines; U373MG, PC3, Hop62, HL60, HCT15, SK-OV-3, HeLa and MCF-7 by SRB assay which revealed significant regression specifically for HCT15, HOP62, MCF-7 and SK-OV-3 human cancer cell lines (GI 50 value < 10) as compared to the standard drug Adriamycin. Systemic toxicity of 1 was carried out by the estimation of oxidative stress biomarkers such as lipid peroxides (expressed as malondialdehyde; MDA) and reduced glutathione (GSH) levels in kidney and liver homogenates and the study was supported by the histopathologic examination of kidney and liver of female Wistar rats.

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Double piperazinediium and 1,4-diazabicyclo[2.2.2]octanediium MII selenates (MII=CoII, NiII, CuII, ZnII) as effective catalysts for Henry reaction

Cited by 21 publications

References 24 publications

A new cyclic binuclear Ni(II) complex as a catalyst towards nitroaldol (Henry) reaction

A new cyclic binuclear Ni(II) complex as a catalyst towards nitroaldol (Henry) reaction

Structure Evolution and Thermal Decomposition of Supramolecular and Lamellar Hybrid Sulfates Templated by 4-Aminopyridinium

Crystal structure determination, spectroscopic characterization and biological profile of a tailored ionic molecular entity, Sn(iv) iminodiacetic acid–piperazinediium conjugate: in vitro DNA/RNA binding studies, Topo I inhibition activity, cytotoxic and systemic toxicity studies

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