3232-37-9Relevant academic research and scientific papers
Supramolecular catalytic synthesis of a novel bis(salicylaldehyde hydrazone) ligand for ratiometric recognition of AT-DNA
Shu, Zhengning,Chen, Yan,Yu, Hui,Liao, Xiaoyu,Liu, Chuanfeng,Tang, Haodong,Li, Sicong,Yang, Peng
, p. 5491 - 5494 (2019)
Hydrazone bond formation under physiological conditions remains challenging. In this study, bis(salicylaldehyde hydrazone) was synthesized using supramolecular catalysis under physiological conditions and its AT-DNA ratiometric sensing properties were ide
Monoorgano-gallium and –indium complexes derived from dianionic tridentate ONO Schiff bases: Synthesis, crystal structures and photoluminescence
Pal, Manoj K.,Kushwah, Nisha,Wadawale, Amey P.,Dey, Sandip,Sudarsan,Jain, Vimal K.
, p. 128 - 133 (2016)
Reactions of triorgano-gallium and –indium etherates with N′-(2-hydroxybenzylidine)benzohydrazide and N′-(2-hydroxy-3-methoxybenzylidine)benzohydrazide in refluxing benzene afforded complexes of composition [{RM}{–O(C6H3R′-3)CH[dbnd]
Binuclear copper complexes: Synthesis, X-ray structure and interaction study with nucleotide/protein by in vitro biochemical and electrochemical analysis
Alagesan,Bhuvanesh,Dharmaraj
, p. 281 - 293 (2014)
Two new, binuclear copper(II) hydrazone complexes have been synthesized and characterized by various physico-chemical techniques including single crystal X-ray diffraction. Interaction of these complexes with nucleotide and protein were analyzed by in vit
Intramolecular Catalysis of Hydrazone Formation of Aryl-Aldehydes via ortho -Phosphate Proton Exchange
Dilek, Ozlem,Sorrentino, Anthony M.,Bane, Susan
, p. 1335 - 1338 (2016)
Bioorthogonal site-specific chemical reaction to label biomolecules in vitro and in living cells is one of the most powerful and convenient tools in chemical biology. Reactive pairs frequently used for chemical conjugation are aldehydes/ketones with hydrazines/hydrazides/hydroxylamines. Although the reaction is generally specific for the two components, even in a cellular environment, the reaction is very slow under physiological conditions. Addition of a phosphate group at the ortho position of an aromatic aldehyde increases the reaction rate by an order of magnitude and enhances the aqueous solubility of the reagent and the product. We have synthesized phosphate-substituted aldehyde synthetic models to study kinetics of their reactions with hydrazines and hydrazides that contain a fluorophore. This rapid bioorthogonal reaction should therefore be potentially a very useful reaction for routine site-specific chemical ligations to study and image complex cellular processes in biological systems.
DNA/BSA interaction, bio-activity, molecular docking simulation study and electrochemical properties of hydrazone Schiff base derived Cu(II)/Ni(II) metal complexes: Influence of the nuclearity and metal ions
Fekri, Roghayeh,Salehi, Mehdi,Asadi, Asadollah,Kubicki, Maciej
, p. 175 - 187 (2017)
Three new transition metal complexes of a tridentate Schiff base ligand, H2L?=?N-(2-hydroxybenzylideneamino) benzamide, were synthesized in the presence of pyridine, 3-methylpyridine and the corresponding metal salts, and were characterized by
Mixed-ligand aroylhydrazone complexes of molybdenum: Synthesis, structure and biological activity
Pasayat, Sagarika,Dash, Subhashree P.,Saswati,Majhi, Paresh Kumar,Patil, Yogesh P.,Nethaji,Dash, Hirak R.,Das, Surajit,Dinda, Rupam
, p. 198 - 204 (2012)
The reaction of the benzoylhydrazone of 2-hydroxybenzaldehyde (H 2L) with [MoO2(acac)2] proceeds smoothly in refluxing ethanol to afford an orange complex [MoO2L(C 2H5OH)] (1). The substrat
Diazaborines Are a Versatile Platform to Develop ROS-Responsive Antibody Drug Conjugates**
Aguiar, Sandra I.,André, Ana S.,António, Jo?o P. M.,Bernardes, Gon?alo J. L.,Carvalho, Joana Inês,Dias, Joana N. R.,Faustino, Hélio,Gois, Pedro M. P.,Lopes, Ricardo M. R. M.,Veiros, Luis F.,da Silva, Frederico A.
supporting information, p. 25914 - 25921 (2021/11/09)
Antibody–drug conjugates (ADCs) are a new class of therapeutics that combine the lethality of potent cytotoxic drugs with the targeting ability of antibodies to selectively deliver drugs to cancer cells. In this study we show for the first time the synthesis of a reactive-oxygen-species (ROS)-responsive ADC (VL-DAB31-SN-38) that is highly selective and cytotoxic to B-cell lymphoma (CLBL-1 cell line, IC50 value of 54.1 nM). The synthesis of this ADC was possible due to the discovery that diazaborines (DABs) are a very effective ROS-responsive unit that are also very stable in buffer and in plasma. DFT calculations performed on this system revealed a favorable energetic profile (ΔGR=?74.3 kcal mol?1) similar to the oxidation mechanism of aromatic boronic acids. DABs’ very fast formation rate and modularity enabled the construction of different ROS-responsive linkers featuring self-immolative modules, bioorthogonal functions, and bioconjugation handles. These structures were used in the site-selective functionalization of a VL antibody domain and in the construction of the homogeneous ADC.
Carbonylative Suzuki coupling reactions catalyzed by ONO pincer–type Pd(II) complexes using chloroform as a carbon monoxide surrogate
Layek, Samaresh,Agrahari, Bhumika,Ganguly, Rakesh,Das, Parthasarathi,Pathak, Devendra D.
, (2020/01/25)
Benzoylhydrazone Schiff base–ligated three new ONO pincer–type palladium(II) complexes, [(PdL1(PPh3)] (1), [(PdL2(PPh3)] (2), and [(PdL3(PPh3)] (3), were synthesized by the reaction of the respective ligand, N-(2-hydroxybenzylidene)benzohydrazide (HL1), N-(2-hydroxy-3-methoxybenzylidene)benzohydrazide (HL2), or N-(5-bromo-2-hydroxybenzylidene) benzohydrazide (HL3), with Pd(OAc)2 and PPh3 in methanol and isolated as air-stable reddish-orange crystalline solids in high yields (78%–83%). All three complexes were fully characterized by elemental analysis, Fourier-transform infrared spectroscopy, UV–Visible, 1H nuclear magnetic resonance (NMR), 13C{1H} NMR, and 31P{1H} NMR spectroscopic studies. The molecular structure of all three complexes was established unambiguously by single-crystal X-ray diffraction studies which revealed a distorted square planar geometry of all three complexes. The ONO pincer–type ligands occupied three coordination sites at the palladium, while the fourth site is occupied by the monodentate triphenylphosphine ligand. The catalytic potential of all three complexes was explored in the carbonylative Suzuki coupling of aryl bromides and iodides with arylboronic acids to yield biaryl ketones, using CHCl3 as the source of carbonyl. The reported protocol is convenient and safe as it obviates the use of carbon monoxide (CO) balloons or pressured CO reactors which are otherwise needed for the carbonylation reactions. The methodology has been successfully applied to the synthesis of two antineoplastic drugs, namely, phenstatin and naphthylphenstatin, in good yields (81% and 85%, respectively). Under the optimized reaction conditions, complex 2 exhibited the best catalytic activity in the carbonylative Suzuki couplings. The reported catalysts have wide reaction scope with good functional group tolerance. All catalysts could be retrieved from the reaction after completion and recycled up to three times with insignificant loss in the catalytic activity.
Tetrabromomethane as an Organic Catalyst: a Kinetic Study of CBr4-Catalyzed Schiff Condensation
Bolotin, Dmitrii S.,Kukushkin, Vadim Yu.,Tolstoy, Peter M.,Vovk, Mikhail A.,Yunusova, Sevilya N.
supporting information, p. 6763 - 6769 (2020/10/27)
Tetrabromomethane functions as an organic catalyst for non-redox reactions of carbonyl species and, in particular, it enhances the aldehyde–acyl hydrazide condensation to give N-acyl hydrazones. This simple, inexpensive, and commercially available halomet
BF3-Etherate-catalyzed tandem reaction of 2-formylarylketones with electron-rich arenes/heteroarenes: An assembly of isobenzofurans
Mishra, Pawan K.,Kumar, Ankit,Verma, Akhilesh K.
supporting information, p. 6122 - 6125 (2020/06/18)
An efficient and BF3·Et2O-catalyzed chemoselective synthesis of diversified 1,3-diarylisobenzofuran in a high yield has been described. The reaction proceeds through sequential hydroarylation-cyclization between 2-formylarylketones and electron-rich arenes/heteroarenes. Advantageous features of the developed methodology include operational simplicity, a broad substrate scope, and applicability towards gram scale synthesis. The utility of isobenzofuran derivatives as the diene was extended to the synthesis of [4+2] cyclo-adducts with DMAD and the synthesis of 1,2-dicarbonylarenes in good yields.
