Topic
Hydrazone
About: Hydrazone is a research topic. Over the lifetime, 4853 publications have been published within this topic receiving 65160 citations. The topic is also known as: hydrazone.
Papers published on a yearly basis
Papers
More filters
TL;DR: An unprecedented visible-light-induced direct C-H bond difluoroalkylation of aldehyde-derived hydrazones was developed, which represents a new way to synthesize substituted hydrazone synthesis rather than classical amine synthesis.
Abstract: An unprecedented visible-light-induced direct C−H bond difluoroalkylation of aldehyde-derived hydrazones was developed. This reaction represents a new way to synthesize substituted hydrazones. The salient features of this reaction include difluorinated hydrazone synthesis rather than classical amine synthesis, extremely mild reaction conditions, high efficiency, wide substrate scope, ease in further transformations of the products, and one-pot syntheses. Mechanistic analyses and theoretical calculations indicate that this reaction is enabled by a novel aminyl radical/polar crossover mechanism, with the aminyl radical being oxidized into the corresponding aminyl cation through a single electron transfer (SET) process.
164 citations
TL;DR: It is reported that simple, commercially available anthranilic acids and aminobenzoic acids act as superior catalysts for hydrazone and oxime formation, speeding the reaction considerably over the traditional aniline-catalyzed reaction at neutral pH.
Abstract: The formation of oximes and hydrazones is widely used in chemistry and biology as a molecular conjugation strategy for achieving ligation, attachment, and bioconjugation. However, the relatively slow rate of reaction has hindered its utility. Here, we report that simple, commercially available anthranilic acids and aminobenzoic acids act as superior catalysts for hydrazone and oxime formation, speeding the reaction considerably over the traditional aniline-catalyzed reaction at neutral pH. This efficient nucleophilic catalysis, involving catalyst–imine intermediates, allows rapid hydrazone/oxime formation even with relatively low concentrations of the two reactants. The most efficient catalysts are found to be 5-methoxyanthranilic acid and 3,5-diaminobenzoic acid; we find that they can enhance rates by factors of as much as 1–2 orders of magnitude over the aniline-catalyzed reaction. Evidence based on a range of differently substituted arylamines suggests that the ortho-carboxylate group in the anthranila...
159 citations
TL;DR: In this article, a solid-phase synthesis for replacing a main-chain hydrogen bond (NH → OCRNH) with a hydrazone link (N−NCH−CH2CH2) in peptides is described.
Abstract: Proteins are characterized by extensive hydrogen bonding that defines regular and irregular substructures. However, hydrogen bonds are weak and insufficient for stabilizing peptide conformation in water. Consequently, the biological activity of peptides is reduced. This led us to test whether a covalent mimic of the hydrogen bond could be used to stabilize peptide conformation in water. A solid-phase synthesis is described for replacing a main-chain hydrogen bond (NH → OCRNH) with a hydrazone link (N−NCH−CH2CH2) in peptides. The synthesis is easy to implement, rapid, and capable of high yields. The replacement of a putative (i + 4 → i) hydrogen bond with the hydrazone at the N terminus of acetyl-GLAGAEAAKA-NH2 (1) to give [JLAZ]AEAAKA-NH2 (2) converts it to a full-length α-helix in water at ambient temperature as indicated by NMR spectroscopy. The observation of weak dαN(i, i + 3), medium dNN(i, i + 1), and strong dαβ(i, i + 3) NOEs that span 2 establish the formation of a full-length α-helix in water. Jα...
158 citations
TL;DR: An efficient and mechanistically interesting method for the synthesis of highly substituted isoquinolines by a Rh(III)-catalyzed hydrazone directed ortho C-H bond activation and annulation without an external oxidant is described.
156 citations
TL;DR: The effect of complexes 5-8 to arrest the growth of HeLa and Hep-2 tumour cell lines has been studied along with the cell viability against the non-cancerous NIH 3T3 cells under in vitro conditions.
Abstract: Four new bivalent nickel hydrazone complexes have been synthesised from the reactions of [NiCl2(PPh3)2] with H2L {L = dianion of the hydrazones derived from the condensation of salicylaldehyde or o-hydroxy acetophenone with p-toluic acid hydrazide (H2L1) (1), (H2L2) (2) and o-hydroxy acetophenone or o-hydroxy naphthaldehyde with benzhydrazide (H2L3) (3) and (H2L4) (4)} and formulated as [Ni(L1)(PPh3)] (5), [Ni(L2)(PPh3)] (6), [Ni(L3)(PPh3)] (7) and [Ni(L4)(PPh3)] (8). Structural characterization of complexes 5–8 were accomplished by using various physico-chemical techniques. In order to study the influence of substitution in the ligand and its planarity on the biological activity of complexes 5–8 containing them, suitable hydrazone ligands 1–4 have been selected in this study. Single crystal diffraction data of complexes 5, 7 and 8 proved the geometry of the complexes to be distorted square planar with a 1 : 1 ratio between the metal ion and the coordinated hydrazones. To provide more insight on the mode of action of complexes 5–8 under biological conditions, additional experiments involving their interaction with calf thymus DNA (CT DNA) and bovine serum albumin (BSA) were monitored by UV-visible and fluorescence titrations respectively. Further, the ligands 1–4 and corresponding nickel(II) chelates 5–8 have been tested for their scavenging effect towards OH and O2− radicals. The effect of complexes 5–8 to arrest the growth of HeLa and Hep-2 tumour cell lines has been studied along with the cell viability against the non-cancerous NIH 3T3 cells under in vitro conditions.
152 citations