1395103-14-6Relevant articles and documents
Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes
Bian, Xue-Wei,Zhang, Ling,Shoberu, Adedamola,Zou, Jian-Ping
supporting information, (2021/04/02)
A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.
Lewis or Br?nsted? A Rectification of the Acidic and Aromatic Nature of Boranol-Containing Naphthoid Heterocycles
Ang, Hwee Ting,Ferguson, Michael J.,Hall, Dennis G.,Johnson, Matthew A.,Kazmi, M. Zain H.,Paladino, Marco,Rygus, Jason P. G.
supporting information, p. 10143 - 10156 (2021/07/21)
Boron-containing heterocycles are important in a variety of applications from drug discovery to materials science; therefore a clear understanding of their structure and reactivity is desirable to optimize these functions. Although the boranol (B-OH) unit of boronic acids behaves as a Lewis acid to form a tetravalent trihydroxyborate conjugate base, it has been proposed that pseudoaromatic hemiboronic acids may possess sufficient aromatic character to act as Br?nsted acids and form a boron oxy conjugate base, thereby avoiding the disruption of ring aromaticity that would occur with a tetravalent boronate anion. Until now no firm evidence existed to ascertain the structure of the conjugate base and the aromatic character of the boron-containing ring of hemiboronic "naphthoid"isosteres. Here, these questions are addressed with a combination of experimental, spectroscopic, X-ray crystallographic, and computational studies of a series of model benzoxazaborine and benzodiazaborine naphthoids. Although these hemiboronic heterocycles are unambiguously shown to behave as Lewis acids in aqueous solutions, boraza derivatives possess partial aromaticity provided their nitrogen lone electron pair is sufficiently available to participate in extended delocalization. As demonstrated by dynamic exchange and crossover experiments, these heterocycles are stable in neutral aqueous medium, and their measured pKa values are consistent with the ability of the endocyclic heteroatom substituent to stabilize a partial negative charge in the conjugate base. Altogether, this study corrects previous inaccuracies and provides conclusions regarding the properties of these compounds that are important toward the methodical application of hemiboronic and other boron heterocycles in catalysis, bioconjugation, and medicinal chemistry.
A Green Synthesis and Antibacterial Activity of N-Arylsulfonylhydrazone Compounds
Yang, Qian,Hao, Wangwang,He, Yangqing,Zhang, Qian,Yu, Xiaojiao,Hua, Yaobing
, p. 152 - 156 (2020/01/28)
A green method has been developed for the synthesis of N-arylsulfonylhydrazones via a simple grindstone procedure. By grinding mixtures of benzensulfonyl hydrazides and a series of aryl aldehydes or ketones in the mortar using L-tyrosine as catalyst, 24 N
Light-Induced Tetrazole-Quinone 1,3-Dipolar Cycloadditions
Ortiz-Rojano, Laura,Rojas-Martín, Jaime,Rodríguez-Diaz, Ciro,Carre?o, M. Carmen,Ribagorda, Maria
supporting information, p. 15050 - 15054 (2019/11/13)
Quinones were firstly used as dipolarophiles in a photoclick 1,3-cycloaddition with 2,5-diaryltetrazoles, as photoactivatable predipoles, providing a novel and efficient access to three types of pyrazole-fused quinones (indazoledione derivatives). Distinc
Tetrazole-Based Probes for Integrated Phenotypic Screening, Affinity-Based Proteome Profiling, and Sensitive Detection of a Cancer Biomarker
Cheng, Ke,Lee, Jun-Seok,Hao, Piliang,Yao, Shao Q.,Ding, Ke,Li, Zhengqiu
supporting information, p. 15044 - 15048 (2017/11/20)
Target-identification phenotypic screening has been a powerful approach in drug discovery; however, it is hindered by difficulties in identifying the underlying cellular targets. To address this challenge, we have combined phenotypic screening of a fully functionalized small-molecule library with competitive affinity-based proteome profiling to map and functionally characterize the targets of screening hits. Using this approach, we identified ANXA2, PDIA3/4, FLAD1, and NOS2 as primary cellular targets of two bioactive molecules that inhibit cancer cell proliferation. We further demonstrated that a panel of probes can label and/or image annexin A2 (a cancer biomarker) from different cancer cell lines, thus providing opportunities for potential cancer diagnosis and therapy.
Synthesis, biological evaluation and molecular docking of new benzenesulfonylhydrazone as potential anti-trypanosoma cruzi agents
Elizondo-Jimenez, Silvia,Moreno-Herrera, Antonio,Reyes-Olivares, Rogelio,DorantesGonzalez, Edith,Nogueda-Torres, Benjamín,De Oliveira, Eduardo Alves Gamosa,Romeiro, Nelilma C.,Lima, Lídia Moreira,Palos, Isidro,Rivera, Gildardo
, p. 149 - 158 (2017/02/05)
Background: Chagas disease is a public health problem caused by Trypanosoma cruzi. Cruzain is a pharmacological target for designing a new drug against this parasite. Hydrazone and N-acylhydrazone derivatives have been traditionally associated as potentia
Developing new chemical tools for DNA methyltransferase 1 (DNMT 1): A small-molecule activity-based probe and novel tetrazole-containing inhibitors
Zhu, Biwei,Ge, Jingyan,Yao, Shao Q.
, p. 2917 - 2927 (2015/03/30)
DNA methylation is an important epigenetic modification catalyzed by DNA methyltransferases (DNMTs). Abnormal expression of endogenous DNMTs in human causes alterations in the genome methylation patterns which subsequently lead to the development of cance
Base-catalyzed N -N bond cleavage of hydrazones: Synthesis of α-amino ketones
Tang, Hai-Tao,Zhou, Yun-Bing,Zhu, Yu,Sun, Hong-Chao,Lin, Min,Zhan, Zhuang-Ping
supporting information, p. 1278 - 1281 (2014/05/06)
An efficient Cs2CO3-promoted synthesis of α-amino ketones using hydrazines, aldehydes, and α-haloketones as starting materials through a cascade condensation/nucleophilic substitution/N -N bond cleavage route is developed. The carbonyl group plays a key role in this novel N -N bond cleavage process. Breaking good: A novel method of base-catalyzed N -N bond cleavage of hydrazones has been discovered. A variety of α-amino ketones was synthesized using hydrazines, α-haloketones, and benzaldehyde as starting materials through a cascade condensation/ nucleophilic substitution/N -N bond cleavage sequence.
Tandem reaction of propargyl alcohol and N-sulfonylhydrazone: Synthesis of dihydropyrazole and its utility in the preparation of 3,3-diarylacrylonitrile
Zhu, Yuanxun,Wen, Shan,Yin, Guangwei,Hong, Deng,Lu, Ping,Wang, Yanguang
supporting information; experimental part, p. 3553 - 3555 (2011/09/14)
An efficient and straightforward strategy for the synthesis of 4-methylene-1-(phenylsulfonyl)-4,5-dihydro-1H-pyrazole from propargyl alcohol and N-sulfonylhydrazone is described. N-Sulfonyl allenamide is postulated to be the key intermediate for this tandem transformation.
