2215-33-0Relevant academic research and scientific papers
New copper(II) complexes of pyridine-2-carboxaldehyde-N-(2-pyridyl)hydrazone and 2-hydroxy-1-naphthaldehyde-semicarbazone: Synthesis, characterization, DNA binding and antimicrobial activity studies
U-Wang, Oinam,Singh, Raj Kumar Bhubon,Singh, Usam Ibotomba,Ramina,Singh, Thoudam Surchandra,Swu, Toka,Brajakishore Singh
, p. 2783 - 2792 (2020)
Two new copper(II) complexes of pyridine-2-carboxaldehyde-N-(2-pyridyl)hydrazone [Cu(PCPH)(H2O)2](NO3)(H2O)2 (1) and 2-hydroxy-1-naphthaldehyde-semicarbazone [Cu(II)(HNSC)H2O]·NO3·H2O (2) have been synthesized and characterized by spectroscopic techniques and single crystal X-ray diffraction study. Complex 1 crystallized as square pyramidal coordination complex in triclinic crystal system while complex 2 crystallized as square planar complex in monoclinic crystal system. EPR spectral patterns are of normal order of energy levels, i.e. x2-y2 >> z2 > xy > xz, yz, with partial covalent character. Both copper(II) complexes were found to be groove binding to calf-thymus DNA and showed activity against E. coli, S. aureus, B. cereus and E. faccium.
Synthesis, Biological Activity, and Mechanism of Action of 2-Pyrazyl and Pyridylhydrazone Derivatives, New Classes of Antileishmanial Agents
Coimbra, Elaine S.,Antinarelli, Luciana M. R.,de A. Crispi, Mariana,Nogueira, Thais C. M.,Pinheiro, Alessandra C.,de Souza, Marcus V. N.
, p. 1387 - 1394 (2018)
In this work, we report the antileishmanial activity of 23 compounds based on 2-pyrazyl and 2-pyridylhydrazone derivatives. The compounds were tested against the promastigotes of Leishmania amazonensis and L. braziliensis, murine macrophages, and intracellular L. amazonensis amastigotes. The most potent antileishmanial compound was selected for investigation into its mechanism of action. Among the evaluated compounds, five derivatives [(E)-3-((2-(pyridin-2-yl)hydrazono)methyl)benzene-1,2-diol (2 b), (E)-4-((2-(pyridin-2-yl)hydrazono)methyl)benzene-1,3-diol (2 c), (E)-4-nitro-2-((2-(pyrazin-2-yl)hydrazono)methyl)phenol (2 s), (E)-2-(2-(pyridin-2-ylmethylene)hydrazinyl)pyrazine (2 u), and (E)-2-(2-((5-nitrofuran-2-yl)methylene)hydrazinyl)pyrazine (2 v)] exhibited significant activity against L. amazonensis amastigote forms, with IC50 values below 20 μm. The majority of the compounds did not show any toxic effect on murine macrophages. Preliminary studies on the mode of action of members of this hydrazine-derived series indicate that the accumulation of reactive oxygen species (ROS) and disruption of parasite mitochondrial function are important for the pharmacological effect on L. amazonensis promastigotes.
Determination of the binding constants of propeller-like metal complexes of picolinaldehyde-2-pyridylhydrazone
Carmona-Vargas, Christian C.,Aristizábal, Sandra L.,Belalcázar, María I.,D'Vries, Richard F.,Chaur, Manuel N.
, p. 275 - 280 (2019)
Herein, we determined the binding constants for transition metal complexes of Cu2+, Co2+, Fe2+, Ni2+, and Zn2+ ions formed with the ligand picolinaldehyde-2-pyridylhydrazone (PapyH) using the Benesi-Hildebrand method. Stoichiometry 2:1 (ligand: metal) was previously determined by the Job's method and confirmed by single-crystal X-ray diffraction finding a propeller-like structure of the [Fe(Papy)2] compound. PapyH and the metal complexes were characterized by 1H NMR and UV-Vis spectroscopy, respectively. The Cu2+ complex exhibited the highest stability constant, which was confirmed by competitive reaction of different metal ions with the ligand PapyH.
Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone
Xia, Hongyu,Wang, Ganghu,Zhao, Dongbo,Zhu, Chunyin
supporting information, p. 922 - 929 (2022/02/10)
A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w
Synthesis and antimycobacterial evaluation of pyridinyl- and pyrazinylhydrazone derivatives
Pinheiro, Alessandra C.,Nogueira, Thaís C. M.,Pereira, Gabriela E.,Louren?o, Cristina,de Souza, Marcus V. N.
, p. 1662 - 1668 (2020/07/06)
Bioisosteric replacements are often tried goaling to affect the lipophilicity, polarity, and aqueous solubility of the substances, as a way to obtain therapeutically improved medicines. Also, hydrazonyl compounds are described with a wide range of pharmac
Metal transition complexes of tridentate Schiff base ligands derived from 2-hydrazinopyridine: synthesis, spectroscopic characterization and X-ray structures
Diop, Amar,Sarr, Mamou,Diop, Mayoro,Thiam, Ibrahima Elhadj,Barry, Aliou Hamady,Coles, Simon,Orton, James,Gaye, Mohamed
, p. 415 - 423 (2019/05/10)
Mononuclear complexes of 1-(pyridin-2-ylmethylidene)-2-(pyridin-2-yl)hydrazine (HL1) and 1-(pyridin-2-yl)-2-(1-(pyridin-2-yl)ethylidene)hydrazine (HL2), [Mn(HL1)(Cl2)(H2O)] (1), [Zn(HL1)(CH3COO)2]·(H2O)3 (2), [Mn(HL2)2]·(ClO4)2 (3) and [Cu(HL2)(NO3)2(H2O)] (4) were synthesized and characterized by physicochemical and spectroscopic methods and X-ray structure determination. The mononuclear compounds 1, 2 and 4 contain one ligand molecule per metal atom while the manganese (II) atom in compound 3 is coordinated to two ligand molecules. Both ligands coordinated to the transition metal center in?a tridentate fashion through two Npyridyl atoms and one Nimino atom. The chloride and acetate anions coordinate in monodentate manner, respectively, in complex 1 and in complex 2. In complex 3, the perchlorate groups remain uncoordinated. In complex 4, the nitrate anions act in unidentate fashion. The molar conductance value indicates that the complexes obtained from HL1 are non-electrolytes while those obtained from HL2 are 2:1 electrolytes in DMF solutions. The X-ray structures reveal octahedral geometry for complexes 1, 3, 4 and trigonal bipyramidal environment for 2.
Electrochemical synthesis of 1,2,4-triazole-fused heterocycles
Ye, Zenghui,Ding, Mingruo,Wu, Yanqi,Li, Yong,Hua, Wenkai,Zhang, Fengzhi
supporting information, p. 1732 - 1737 (2018/04/30)
A reagent-free intramolecular dehydrogenative C-N cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram scale easily. This novel method was applied to the synthesis of one of the top-selling drugs Xanax and late stage functionalization for generating chemical diversity in biologically relevant lead molecules.
Manganese-Catalyzed Direct Olefination of Methyl-Substituted Heteroarenes with Primary Alcohols
Barman, Milan K.,Waiba, Satyadeep,Maji, Biplab
supporting information, p. 9126 - 9130 (2018/07/25)
Herein, we present the first catalytic direct olefination of methyl-substituted heteroarenes with primary alcohols through an acceptorless dehydrogenative coupling. The reaction is catalyzed by a complex of the earth-abundant transition metal manganese that is stabilized by a bench-stable NNN pincer ligand derived from 2-hydrazinylpyridine. The reaction is environmentally benign, producing only hydrogen and water as byproducts. A large number of E-disubstituted olefins were selectively obtained with high efficiency.
Lanthanide(III) complexes with tridentate Schiff base ligand, antioxidant activity and X-Ray crystal structures of the Nd(III) and Sm(III) complexes
Gueye, Mbossé Ndiaye,Dieng, Moussa,Thiam, Ibrahima Elhadji,Lo, Djiby,Barry, Aliou Hamady,Gaye, Mohamed,Retailleau, Pascal
, p. 8 - 15 (2017/03/31)
The tridentate N4-type Schiff base was synthesized from the condensation reaction of 2-hydrazinopyridine and pyridine-2-carbaldehyde. Neodymium and Samarium complexes were isolated when the corresponding nitrate salt was added to the solution of the ligand. The isolated compounds were characterized by elemental analyses, IR study, room temperature magnetic measurements and single X-ray crystal diffraction of the two crystals. Both complexes crystallize in the monoclinic system with space group P21/c. The cell parameters of the Nd complex are a = 11.0927(8) ?, b = 17.9926 (13) ?, c = 11.9395(9) ? and β = 115.274(5) ° while the Sm complex shows parameters cell of a = 11.0477(8) ?, b = 17.9254(13) ?, c = 11.9149(8) ? and β = 115.489(5) °. The X-ray study reveals isotopic Nd/Sm binuclear structures were each metal ion is nine-coordinated in the same fashion. Both metal centers have distorted tricapped trigonal prism geometry, with the Schiff base acting as tridentate ligand. The DPPH? radical scavenging effects of the Schiff base ligand and its Ln(III) complexes were screened. The Ln(III) complexes were significantly more efficient in quenching DPPH? than the free Schiff base ligand.
Synthesis, characterization and antioxidant activity of lanthanide(III) complexes with tridentate Schiff base ligand. X-ray crystal structure of the Ce(III) complex
Ndiaye Gueye, Mbossé,Dieng, Moussa,Thiam, Ibrahima Elhadji,Sow, Mouhamadou Moustapha,Gueye Sylla, Rokhaya,Barry, Aliou Hamady,Gaye, Mohamed,Retailleau, Pascal
, p. 35 - 41 (2017/07/22)
The tridentate N4-type Schiff base was synthesized in situ from the condensation reaction of 2-hydrazinopyridine and pyridine-2-carbaldehyde. Novel lanthanide(III) complexes were isolated when lanthanide(III) nitrate salt were added to the solution of the ligand. The complexes were characterized by IR spectra, room temperature magnetic measurement, elemental analyses and the structure of the Ce(III) complex was determined by X-ray single crystal diffraction . The complex crystallizes in the monoclinic system with space group P21/c. The geometry around the metal center shows distorted tricapped trigonal prism. It is noteworthy that the tridentate Schiff base acts as tridentate ligand leading nine-coordinate complex.
