4335-90-4Relevant articles and documents
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Yamashita et al.
, p. 1867 (1975)
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Investigation of in vitro anticancer and DNA strap interactions in live cells using carboplatin type Cu(II) and Zn(II) metalloinsertors
Pravin, Narayanaperumal,Raman, Natarajan
, p. 675 - 687 (2014)
A series of carboplatin type Cu(II) and Zn(II) metalloinsertors (1-8) having β-diketone analogues and biologically significant cyclobutane-1,1-dicarboxylic acid have been synthesized and characterized by spectral and analytical methods. The binding and cleavage propensity of these metalloinsertors on DNA and their cytotoxic effects in live cells have been explored. From the gel electrophoresis study, it is observed that the complexes 1-8 cleave pBR322 DNA via a hydrolytic mechanism induced by hydroxyl radical scavengers, DMSO and EtOH as the reactive oxygen species (ROS). In vivo antitumor efficacy has been studied on EAC tumor bearing mice which is assessed by mean survival time, effect on hematological parameters and solid tumor volume. The results strongly support that complex 1 shows potent antitumor effect against EAC and higher than the standard drug carboplatin. Moreover, the cytotoxicity of the complexes, screened on a panel of human cancerous cell lines viz., human cervical cancer cells (HeLa), human breast adenocarcinoma cells (MCF-7), human laryngeal epithelial carcinoma cells (HEp-2), human liver carcinoma cells (Hep G2) and non-cancerous NIH 3T3 mouse embryonic fibroblasts cell lines, reveals that complex 1 exhibits a better anticancer activity than other complexes and standards.
Mechanism and free energy profile of base-catalyzed Knoevenagel condensation reaction
Dalessandro, Ellen V.,Collin, Hugo P.,Valle, Marcelo S.,Pliego, Josefredo R.
, p. 57803 - 57810 (2016)
The Knoevenagel condensation reaction is a classical method for carbon-carbon bond formation. This reaction can be catalyzed by homogeneous or heterogeneous bases, and in the past ten years many different solid bases catalysts have been investigated. In this report, we have done a reliable theoretical analysis of the reaction mechanism and free energy profile of acetylacetone reaction with benzaldehyde catalyzed by methoxide ion in methanol solution. The analysis was extended for solventless conditions and solid base catalysis. We have found that the enolate addition to the benzaldehyde is a rapid step, contrary to general assumptions on the mechanism. The rate-determining step is the leaving of the hydroxide ion from the anionic intermediate, with a predicted overall free energy barrier of 28.8 kcal mol-1. This finding explains the experimental observation that more polar medium favor the reaction, once the transition state is product-like and involves the formation of the highly solvated hydroxide ion. The present results provides useful insights on this reaction system.
Reductive Knoevenagel Condensation with the Zn-AcOH System
Ivanov, Konstantin L.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.
, p. 1285 - 1291 (2020/11/13)
An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.
Efficient and recyclable solid acid-catalyzed alkylation of active methylene compound via oxonium intermediate for atom economical synthesis of organic compounds
Naikwadi, Dhanaji R.,Bankar, Balasaheb D.,Ravi, Krishnan,Biradar, Ankush V.
, p. 3691 - 3703 (2021/06/12)
In the present work, we report the catalytic reaction of active methylene compounds with cyclic enol ethers and aryl acetals through oxonium intermediate under solvent-free conditions using heterogeneous solid acid catalysts. Among studied solid acid catalysts, Amberlyst-15 gave excellent yields (35–85%) of alkylated products. The catalyst showed broader substrate scope, and a recyclable catalytic cost-efficient approach of the alkylation was examined on the different types of cyclic enol ethers and aryl acetal.
Iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes
Chen, Weifeng,Jiang, Kezhi,Xue, Yuntian,Yan, Yaolong,Yang, Lei
, p. 14720 - 14724 (2020/04/27)
The first iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes was achieved. The reaction tolerates a wide range of functionalities. Furthermore, this protocol was found to be applicable to the oxidative transformation of allylic acetates. The proposed mechanism involves an oxygen transfer from solvent water to the carbonyl products.
