- Highly selective copper-catalyzed oxidation of benzyl alcohols to aromatic aldehydes in water at room temperature
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Water-soluble 2N2O–Cu(II) complexes were synthesized and used for the catalytic oxidation of benzylic alcohols to the corresponding aldehydes in pure water resulting in high yields of up to 94%. Importantly, the catalytic system exhibits a wide substrate scope, high functional group tolerance and can be reused directly for subsequent reaction cycles. Using this catalytic system, the product 4-methylbenzaldehyde can be produced on a multi-gram scale and in the complete absence of any organic solvent, surfactant or phase transfer reagent. Copyright
- Wu, Jianglong,Liu, Yan,Ma, Xiaowei,Liu, Ping,Gu, Chengzhi,Dai, Bin
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- COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF TUMORS
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The present invention relates to compounds of Formula (Ia) or pharmaceutically acceptable salts, hydrates, solvates, clathrates, polymorphs, stereoisomers thereof. It further discloses a pharmaceutical composition comprising compounds of Formula (Ia) and the use of compounds of Formula (Ib), in particular for the use in the treatment of diseases or disorders wherein disrupting Rad51-BRCA2 interaction is beneficial.
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Page/Page column 89-90
(2021/06/22)
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- Synthetic Lethality in Pancreatic Cancer: Discovery of a New RAD51-BRCA2 Small Molecule Disruptor That Inhibits Homologous Recombination and Synergizes with Olaparib
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Synthetic lethality is an innovative framework for discovering novel anticancer drug candidates. One example is the use of PARP inhibitors (PARPi) in oncology patients with BRCA mutations. Here, we exploit a new paradigm based on the possibility of triggering synthetic lethality using only small organic molecules (dubbed "fully small-molecule-induced synthetic lethality"). We exploited this paradigm to target pancreatic cancer, one of the major unmet needs in oncology. We discovered a dihydroquinolone pyrazoline-based molecule (35d) that disrupts the RAD51-BRCA2 protein-protein interaction, thus mimicking the effect of BRCA2 mutation. 35d inhibits the homologous recombination in a human pancreatic adenocarcinoma cell line. In addition, it synergizes with olaparib (a PARPi) to trigger synthetic lethality. This strategy aims to widen the use of PARPi in BRCA-competent and olaparib-resistant cancers, making fully small-molecule-induced synthetic lethality an innovative approach toward unmet oncological needs.
- Bagnolini, Greta,Milano, Domenico,Manerba, Marcella,Schipani, Fabrizio,Ortega, Jose Antonio,Gioia, Dario,Falchi, Federico,Balboni, Andrea,Farabegoli, Fulvia,De Franco, Francesca,Robertson, Janet,Pellicciari, Roberto,Pallavicini, Isabella,Peri, Sebastiano,Minucci, Saverio,Girotto, Stefania,Di Stefano, Giuseppina,Roberti, Marinella,Cavalli, Andrea
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supporting information
p. 2588 - 2619
(2020/03/05)
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- Direct formylation of fluorine-containing aromatics with dichloromethyl alkyl ethers
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Formylations of fluorine-containing aromatic compounds with dichloromethyl alkyl ethers have been investigated. Dichloromethyl propyl ether and dichloromethyl butyl ether have been applied for the formylation of fluorine-containing anisoles to give the corresponding aldehydes in good yields. Application of these ethers is preferable to that of methyl ether, which is prepared from volatile methyl formate. Reaction of fluorine-containing phenols with these dichloromethyl alkyl ethers did not give salicylaldehyde derivatives, leading instead to corresponding aryl formates in high yields. A plausible mechanism is discussed.
- Warashina, Takuya,Matsuura, Daisuke,Kimura, Yoshikazu
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p. 587 - 593
(2019/07/22)
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- Sodium copper chlorophyllin catalyzed chemoselective oxidation of benzylic alcohols and diarylmethanes in water
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We report the highly efficient and chemoselective oxidation of benzylic alcohols catalyzed by sodium copper chlorophyllin in water, producing corresponding arylcarbonyl compounds. Importantly, the catalytic system exhibits a wide substrate scope and high functional group tolerance. Moreover, secondary alcohols and even diarylmethanes were smoothly oxidized to the desired aryl ketones with excellent yields.
- Liu, Shi-juan,Zhang, Miao,Lu, Rong,Li, Xiu-ying,Che, Guang-bo
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- A simple, mild and efficient oxidation of benzylic alcohols in the presence of NBS/KOAc in aqueous solution
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Background: The oxidation of benzylic alcohols to carbonyl compounds is a fundamental reaction in organic synthesis. In traditional oxidation processes, a large amount of toxic and volatile organic solvents and metal oxidants are used. Thus, developing environmentally benign oxidation processes is an important goal. N-Bromosuccinimide (NBS) is an inexpensive and convenient oxidant widely used in a variety of oxidative reactions under acidic or alkaline conditions. Methods: In this paper, we developed a simple, mild, and efficient oxidation of benzylic alcohols in the presence of N-bromosuccinimide (NBS)/KOAc in aqueous solution (H2O/CH2Cl2 = 3:1). Results: A series of benzylic alcohols were oxidized selectively to the corresponding ketones in moderate to excellent yields at room temperature. Conclusion: This reaction was carried out using a wide variety of substrates, required no metal catalyst, and proved to be tolerant towards a variety of different functional groups.
- Wu, Jianglong,Liu, Yan,Liu, Ping,Gu, Chengzhi
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p. 254 - 260
(2017/07/15)
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- Efficient and Highly Selective Solvent-Free Oxidation of Primary Alcohols to Aldehydes Using Bucky Nanodiamond
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Selective oxidation of alcohols to aldehydes is widely applicable to the synthesis of various green chemicals. The poor chemoselectivity for complicated primary aldehydes over state-of-the-art metal-free or metal-based catalysts represents a major obstacle for industrial application. Bucky nanodiamond is a potential green catalyst that exhibits excellent chemoselectivity and cycling stability for the selective oxidation of primary alcohols in diverse structures (22 examples, including aromatic, substituted aromatic, unsaturated, heterocyclic, and linear chain alcohols) to their corresponding aldehydes. The results are comparable to reported transition-metal catalysts including conventional Pt/C and Ru/C catalysts for certain substrates under solvent-free conditions. The possible activation process of the oxidant and substrates by the surface oxygen groups and defect species are revealed with model catalysts, ex situ electrochemical measurements, and ex situ attenuated total reflectance. The zigzag edges of sp2 carbon planes are shown to play a key role in these reactions.
- Lin, Yangming,Wu, Kuang-Hsu Tim,Yu, Linhui,Heumann, Saskia,Su, Dang Sheng
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p. 3497 - 3505
(2017/09/15)
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- NOVEL NUCLEOSIDE PHOSPHORAMIDATE COMPOUND AND USE THEREOF
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The present invention provides a novel nucleoside phosphoramidate compound, or a stereoisomer, salt, hydrate, solvate or crystal thereof for the treatment of Flaviviridae family viral infection, especially hepatitis C viral infection. The present invention also provides the pharmaceutical composition comprising a compound of the present invention, or a stereoisomer, salt, hydrate, solvate or crystal thereof and a use of the compound or the composition of the present invention in the treatment of Flaviviridae family viral infection, especially hepatitis C viral infection. The compound of the present invention has a good anti-HCV effect.
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Paragraph 0137
(2015/11/24)
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- Elemental fluorine. Part 21. (1) direct fluorination of benzaldehyde derivatives
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Direct fluorination of a range of benzaldehyde derivatives gives mixtures of fluorobenzaldehyde and benzoyl fluoride products in ratios that depend upon the nature of the ring substituent Electron-withdrawing substituents give predominantly benzoyl fluoride derivatives, whereas electron-donating substituents lead to fluoroarene systems. Separation of ring-fluorinated products can be easily accomplished by esterification of the benzoyl fluoride side products. Scale-up of these processes to provide significant quantities of appropriate fluorobenzaldehyde systems has also been achieved using continuous flow techniques.
- Chambers, Richard D.,Sandford, Graham,Trmcic, Jelena,Okazoe, Takashi
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p. 339 - 344
(2013/01/03)
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- Elemental fluorine. Part 20. Direct fluorination of deactivated aromatic systems using microreactor techniques
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Continuous flow microreactor technology has been used for the direct fluorination of a range of deactivated di- and tri-substituted aromatic systems.
- Chambers, Richard D.,Fox, Mark A.,Sandford, Graham,Trmcic, Jelena,Goeta, Andres
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- A new synthesis of aldehydes by the palladium-catalyzed reaction of 2-pyridinyl esters with hydrosilanes
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A new synthesis of aldehydes by the palladium-catalyzed reaction of 2-pyridinyl esters with hydrosilanes is described. The reaction is applicable to the preparation of aliphatic, aromatic, and α,β-unsaturated aldehydes. Various functional groups, such as fluoro, methoxy, aldehyde, acetal, and ester, are tolerated. Georg Thieme Verlag Stuttgart.
- Nakanishi, Jun,Tatamidani, Hiroto,Fukumoto, Yoshiya,Chatani, Naoto
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p. 869 - 872
(2007/10/03)
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- Synthesis and anticancer activity of fluorinated analogues of combretastatin A-4
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The synthesis of a series of fluorinate d benzaldehydes and their use in the Wittig synthesis of fluoro-substituted stilbenes is described. 3,5-Difluoro-4-hydroxybenzaldehyde (6) and 3-fluoro-4-methoxybenzaldehyde (11) are prepared by Duff formylation of 3,5-difluorophenol and 2-fluoroanisole, respectively. 2-Methoxy-3,4-difluorobenzaldehyde was obtained by Friedel-Crafts formylation of 2,3-difluoroanisole with α,α-dichloromethyl methyl ether. The aldehydes were used to make a series of fluorinated analogues of the anticancer combretastatins A-1, A-2 and A-4. The in vitro anticancer properties of the fluoro combretastatins are reported. The most active fluoro analogue 3-deoxy-3-fluoro-combretastatin A-4 (Z-2) retains the potent cell growth inhibitory properties of CA-4.
- Lawrence, Nicholas J.,Hepworth, Lucy A.,Rennison, David,McGown, Alan T.,Hadfield, John A.
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p. 101 - 108
(2007/10/03)
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- Method for treating patient having precancerous lesions with a combination of pyrimidopyrimidine derivatives and esters and amides of substituted indenyl acetic acides
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Combinations of substituted indenyl acetic acids and pyrimido-pyrimidine derivatives are useful in the treatment of colonic polyps and inhibiting the growth of neoplastic cells.
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- Isoquinoline compound melanocortin receptor ligands and methods of using same
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The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.
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- Substituted condensation products of 1H-indenyl-hydroxyalkanes with aldehydes for neoplasia
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Substituted condensation products of 1H-indenylhydroxyalkanes with aldehydes are useful for inducing or promoting apoptosis and for arresting uncontrolled neoplastic cell proliferation, and are specifically useful in the arresting and treatment of neoplasia, including precancerous and cancerous lesions.
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- Substituted methoxy benzylidene indenyl-acetic and propionic acids for treating patients with precancerous lesions
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Substituted methoxy benzylidene indenyl compounds are useful in the treatment of precancerous lesions and neoplasms.
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- Lactone compounds for treating patient with precancerous lesions
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Substituted lactone compounds are useful in the treatment of precancerous lesions and neoplasms.
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- Lactone compounds for treating patients with precancerous lesions
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Substituted lactone compounds are useful in the treatment of precancerous lesions.
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- Method for treating patients with precancerous lesions by administering substituted sulfonyl idenyl acetic and propionic acids and esters to patients with lesions sensitive to such compounds
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Substituted indenyl sulfonyl acetic acids are useful in the treatment of precancerous lesions sensitive to treatment with those sulfonyl compounds.
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- Esters and amides of substituted indenyl acetic acids
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Esters and amides of substituted indenyl acetic acids of the formula: n is an integer of at least 2;, Q is a deprotonated residue of polymer or macromolecular structure having a molecular weight of at least about 1000 containing at least two primary and/or secondary amino groups and/or hydroxy groups;, R1 is selected from hydrogen, lower alkyl, or haloalkyl;, R2 is selected from hydrogen or alkyl;, R3 and R4 are one or more members each independently chosen from hydrogen, alkyl, acyloxy, alkoxy, nitro, amino, acylamino, alkylamino, diakylamino, dialkylaminoalkyl, sulfamyl, alkythio, mercapto, hydroxy, hydroxyalkyl, alkylsulfonyl, halogen, cyano, carboxyl, carbalkoxy, carbamido, haloalkyl or cycloalkoxy; and, R5 is selected from alkylsulfenyl, alkylsulfinyl or alkylsulfonyl. are useful in the treatment of colonic polyps.
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- Process for nucleophilic fluoroalkylation of aldehydes
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Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formula wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
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