3840-31-1Relevant academic research and scientific papers
Adamantane acid esters with alkoxyaryl alcohols: Synthesis, antiproliferative activity, and influence on microtubule network of tumor cells
Zefirov,Nurieva,Pikulina, Yu. A.,Ogon′kov,Wobith,Kuznetsov,Zefirova
, p. 1503 - 1509 (2017)
Adamantaneacetic and adamantanecarboxylic acid esters containing 3-hydroxy-4-methoxybenzyl, 3,4,5-trimethoxybenzyl, or 5-(hydroxymethyl)-2-methoxyphenyl groups were synthesized as unusual analogs of natural antitumor and anti-tubulin agents combretastatin A-4 and 2-methoxyestradiol. The compounds were found to possess noticeable cytotoxicity to epithelial human carcinoma cell line A549 (EC50 = 4.3—81 μmol L–1). An ability to cause complete depolymerization of microtubule network of A549 cells was demonstrated for 5-(hydroxymethyl)-2-methoxyphenyl adamantan-1-ylacetate (6a) at a concentration of 100 μmol L–1. Ester 6a belongs to a new structural type, which is unusual for the ligands of the tubulin colchicine domain, and is an interesting lead compound for further structural optimization.
Visible light photocatalytic reduction of aldehydes by Rh(iii)-H: A detailed mechanistic study
Ghosh,Slanina,K?nig
, p. 2027 - 2034 (2015)
The chemoselective photoreduction of aldehydes in the presence of ketones was achieved using triethanolamine (TEOA) as sacrificial electron donor, proflavine (PF) as photocatalyst and [CpRh(iii)(bpy)Cl]Cl (Rhcat) as mediator. The reducing agent, which reacts with the carbonyl group was found to be [CpRh(iii)(bpy)H]Cl (Rh(iii)-H). Contrary to formate-based reduction, its slow photochemical in situ generation enables to kinetically distinguish aldehydes from ketones. The inherent reactivity difference of the carbonyl compounds is transferred by the method into synthetically useful reaction selectivities. The substrate scope is broad with excellent yields. A detailed study of the reaction mechanism reveals that the photoreduction of the PF triplet and the subsequent reduction of the Rhcat leading to Rh(iii)-H represents the major reaction pathway, which is highly oxygen sensitive. The oxidative quenching of the PF singlet state by Rhcat is a competing mechanism, which prevails in non-degassed systems.
A Michael initiated - condensation - elimination sequence for the stereoselective synthesis of maleate derivatives
Harrowven, David C.,Poon, Hon Suen
, p. 1389 - 1398 (1996)
The paper describes a convenient method for the diastereoselective synthesis of trisubstituted alkenes through the lithium amide mediated union of ketones and diethyl maleate. The reaction has been shown to proceed via a Michael initiated - condensation - elimination (MICE) sequence.
Diethyl Lithiomaleate: Preparation and Use in Synthesis.
Harrowven, David C.,Poon, Hon Suen
, p. 9101 - 9102 (1994)
The paper describes a simple method for the generation and alkylation of diethyl lithiomaleate.These reactions proceed with complete retention of alkene geometry, providing a convenient method for the diastereoselective introduction of this useful four carbon synthon.
Controlled reduction of activated primary and secondary amides into aldehydes with diisobutylaluminum hydride
Azeez, Sadaf,Kandasamy, Jeyakumar,Sabiah, Shahulhameed,Sureshbabu, Popuri
supporting information, p. 2048 - 2053 (2022/03/31)
A practical method is disclosed for the reduction of activated primary and secondary amides into aldehydes using diisobutylaluminum hydride (DIBAL-H) in toluene. A wide range of aryl and alkyl N-Boc, N,N-diBoc and N-tosyl amides were converted into the corresponding aldehydes in good to excellent yields. Reduction susceptible functional groups such as nitro, cyano, alkene and alkyne groups were found to be stable. Broad substrate scope, functional group compatibility and quick conversions are the salient features of this methodology.
Iron-catalyzed chemoselective hydride transfer reactions
Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, (2021/06/07)
A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.
Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming
Chen, Yuwen,Huang, Yulan,Jiao, Wei,Li, Fu,Li, Suiyan,Li, Wenhua,Lin, Yuan,Liu, Wanli,Ma, Yuling,Sheng, Yuwen,Suksamrarn, Apichart,Wang, Fei,Wang, Jing,Wei, Xiao,Wisanwattana, Wisanee,Wu, Wenbi,Zeng, Zhongqiu,Zhang, Guolin,Zhang, Jichao,Zhu, Qiyu
, (2022/01/03)
Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.
Synthesis method of selenium-containing isochroman compound
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Paragraph 0046; 0052, (2021/05/29)
The invention discloses a synthesis method of a selenium-containing isochroman compound. The synthesis method comprises the following steps: under the protection of nitrogen, adding N-phenylseleno saccharin (NPSSac) into a reactor, then adding dichloromethane to completely dissolve the N-phenylseleno saccharin, adding a 1-[(cinnamoxy) methyl]-3, 4, 5-trimethoxy benzene compound and boron trifluoride diethyl etherate after the N-phenylseleno saccharin is completely dissolved, stirring at 20-60 DEG C for 2-6 hours until the reaction is complete, and after the reaction is finished, quenching, extracting, combining organic phases, drying, concentrating, separating and purifying to obtain the selenium-containing isochroman compound. The synthesis method disclosed by the invention is relatively easy to operate, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrial production.
Synthesis method of 2-benzoxepin compound
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Paragraph 0045; 0050, (2021/05/29)
The invention discloses a synthesis method of a 2-benzoxepin compound. The method comprises the following specific steps: under the protection of nitrogen, adding N-phenylseleno-phthalimide into a reactor, then adding anhydrous dichloromethane to dissolve the N-phenylseleno-phthalimide, then adding a 1-[(cinnamyl) methyl]-3, 4, 5-trimethoxybenzene compound, taking zinc chloride as a catalyst, reacting at room temperature, adding saturated sodium bicarbonate for quenching after the reaction is finished, extracting by dichloromethane, combining organic phases, drying by anhydrous magnesium sulfate, concentrating under reduced pressure, and performing silica gel rapid chromatographic purification by thin-layer chromatography silica gel to obtain the 2-benzoxepin compound. The method is simple in reaction operation, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrialized production.
Synthesis method of isochroman compound
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Paragraph 0046; 0051; 0060; 0065; 0073; 0078, (2021/05/15)
The invention discloses a synthesis method of an isochroman compound, which comprises the following steps of adding dichloromethane and phosphorus tribromide into 3, 4, 5-trimethoxy benzyl alcohol, and reacting to obtain 1-bromomethyl-3, 4, 5-trimethoxy benzene, adding tetrahydrofuran, cinnamyl alcohol, sodium hydride and 1-bromomethyl-3, 4, 5-trimethoxybenzene into a reactor, and reacting to obtain 1-[(cinnamyl oxy)methyl]-3, 4, 5-trimethoxybenzene, adding cyanuric acid into a reactor containing a potassium hydroxide aqueous solution to react, dropwise adding a silver nitrate aqueous solution, and reacting to obtain silver isocyanurate, adding silver isocyanurate, phenyl selenium bromide and anhydrous dichloromethane into a reactor, and reacting to obtain N, N, N-triphenyl seleno isocyanurate, reacting N, N, N-triphenyl seleno isocyanurate, dichloromethane, boron trifluoride diethyl etherate and a 1-[(cinnamyl oxy)methyl]-3, 4, 5-trimethoxybenzene compound to obtain a target product. The method is simple in reaction operation, mild in reaction condition, relatively high in yield and environment-friendly.
