- Nickel-Catalyzed Esterification of Amides Under Mild Conditions
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Abstract: The use of ligands to adjust the catalytic activity of the catalyst for esterification of amides is challenge in organic chemistry. In this paper, Nickel(II)-NHC-catalyzed the esterification reaction between N,N-di-Boc amide and alcohols at room temperature have been demonstrated. The imidazolium salt bearing a hydroxyl functionalized side arm showed high effective catalytic activity in the activation of the amide N–C bond in air atmosphere. Graphic Abstract: [Figure not available: see fulltext.].
- Li, Jun-Fei,Wang, Yao-Fang,Wu, Yuan-Yuan,Liu, Wen-Jing,Wang, Jun-Wen
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p. 874 - 880
(2019/11/13)
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- New composition for improving skin conditions
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The present invention relates to a composition for improving skin condition which comprises a derivative of a compound represented by chemical formula (I) or a pharmacologically acceptable salt thereof. In the chemical formula (I), X is hydrogen or methoxy, and R is a C1 to C20 linear or branched alkyl group.COPYRIGHT KIPO 2020
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Paragraph 0078-0080
(2020/07/30)
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- Facile, highly efficient and environmentally friendly transesterification mediated by platinum dioxide and nickel oxide under essentially neutral conditions
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A practical, facile and highly efficient transesterification reaction under essentially neutral conditions was achieved using platinum dioxide (PtO2) or PtO2/nickel oxide (NiO) as the catalyst. A number of esters and alcohols that contain various functional groups were employed. Good to excellent yields were obtained for different aromatic or aliphatic starting materials. The Pt-alcohol intermediate generated in situ facilitated the exchange of low-alcohol esters to high-alcohol esters.
- Teng, Binhao,Shi, Jiangong,Yao, Chunsuo
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supporting information
p. 2465 - 2471
(2018/06/11)
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- Design, synthesis, biological evaluation, and 3D-QSAR analysis of podophyllotoxin–dioxazole combination as tubulin targeting anticancer agents
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The advancement of cancer-fighting drugs has never been a simple linear process. Those drug design professionals begin to find inspiration from the nature after failing to find the ideal products by creative drug design and high-throughput screening. To obtain new molecules for inhibiting tubulin, podophyllotoxin was adopted as the leading compound and 1,3,4-oxadiazole was brought in to the C-4 site of podophyllotoxin in this research. A series of seventeen podophyllotoxin-derived esters have been achieved and then evaluated their antitumor activities against four different cancer cell lines: A549, MCF-7, HepG2, and HeLa. Among all the compounds, compound 7c showed the best antiproliferating properties with IC50?=?2.54?±?0.82?μm against MCF-7 cancer cell line. It was obvious that the content of ROS grew significantly in MCF-7 in a way depending on the dosage. The time- and dose-dependent cell cycle assays revealed that compound 7c could apparently block cell cycle in the phase of G2/M along with the upregulation of cyclin A2 and CDK2 protein. According to further studies, confocal microscopy experiment has certified that compound 7c could restrain cancer from growing by blocking the polymerization of microtubule. Meanwhile, compound 7c could be ideally integrated with the colchicine site of tubulin. In future, it would be feasible to selectively design tubulin inhibitors with the help of 3D-QSAR. This means that it is hopeful to develop compound 7c as a potential agent against cancer due to its biological characteristics.
- Wang, Zi-Zhen,Sun, Wen-Xue,Wang, Xue,Zhang, Ya-Han,Qiu, Han-Yue,Qi, Jin-Liang,Pang, Yan-Jun,Lu, Gui-Hua,Wang, Xiao-Ming,Yu, Fu-Gen,Yang, Yong-Hua
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p. 236 - 243
(2017/07/13)
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- Diethyloxalate as “CO” Source for Palladium-Catalyzed Ethoxycarbonylation of Bromo- and Chloroarene Derivatives
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Palladium(II)-catalyzed ethoxycarbonylation of aryl bromides with diethyloxalate oxalate is described. Functionalized aromatic esters can be efficiently synthesized with only 0.65 mol % PdCl2(PPh3)2 catalyst under microwav
- Monrose, Amandine,Salembier, Helori,Bousquet, Till,Pellegrini, Sylvain,Pélinski, Lydie
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supporting information
p. 2699 - 2704
(2017/08/16)
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- Design, Synthesis and Anti-Proliferative Activities of 2,6-Substituted Thieno[3,2-d]pyrimidine Derivatives Containing ElectrophilicWarheads
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Thieno[3,2-d]pyrimidine as an effective pharmacophore has been extensively studied. However, its 2,6-substituted derivatives are rarely reported. In the present study, eighteen 2,6-substituted thieno[3,2-d]pyrimidine derivatives containing electrophilic warheads were designed based on the first known Fibroblast growth factor receptor-4 (FGFR4) inhibitor Blu9931. Unexpectedly, all of the derivatives exhibited negligible activity against FGFR4. However, most of the target compounds exhibited antiproliferative activities against four human cancer cell lines, including A431, NCI-H1975, Ramos and SNU-16. Compound 12 showed the most potent antiproliferative activities on the above four cell lines with IC50 values of 1.4 μM, 1.2 μM, 0.6 μM, and 2.6 μM, respectively. Additionally, the antiproliferative activity of 12 against MDA-MB-221 proved that 12 had the selectivity towards certain tumor cell lines. Furthermore, preliminary structure-Activity relationship analysis was discussed based on the experimental data.
- Zhang, Qiumeng,Hu, Zonglong,Shen, Qianqian,Chen, Yi,Lu, Wei
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- Synthesis method of 3,5-dimethoxybenzoic acid ethyl ester
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The invention discloses a synthesis method of 3,5-dimethoxybenzoic acid ethyl ester, and belongs to the field of chemosynthesis. According to the method, benzene is firstly used for producing resorcinol under specific conditions; under the condition of using dimethylformamide as a solvent by anhydrous potassium carbonate and carbon dioxide, the 3,5-dihydroxy-benzoic acid is finally obtained through impurity removal, decoloring, pH value regulation and cooling crystallization; then, the 3,5-dihydroxy-benzoic acid is mixed with dimethyl sulfate in a stirring condition; a sodium hydroxide solution is dropwise added into the materials for backflow; the pH value is regulated after the backflow; the pressure reduction filtering, washing and drying are carried out after cooling to 0 DEG C; the 3,5-dimethoxybenzoic acid is obtained; finally, the 3,5-dimethoxybenzoic acid is esterified with absolute ethyl alcohol under the condition of concentrated sulfuric acid; finally, the 3,5-dimethoxybenzoic acid ethyl ester is obtained.
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Paragraph 0004; 0006
(2017/01/17)
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- Metal-free aerobic oxidative esterification of aldehydes in the presence of cyanide
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A metal-free aerobic oxidative esterification of aldehydes in the presence of cyanide is described. Various aromatic aldehydes and sterically congested alcohols were amenable to this protocol. In addition, this method could be extended to the preparation of thioesters with a thiol in place of an alcohol. Furthermore, the cyanide-mediated aerobic oxidation of aldehydes was applied to the synthesis of lactones via intramolecular esterification in the absence of an alcohol.
- Kim, Yoo-Jin,Cheon, Cheol-Hong
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supporting information
p. 2055 - 2061
(2015/08/18)
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- Novel 1,3,4-oxadiazole thioether derivatives targeting thymidylate synthase as dual anticancer/antimicrobial agents
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A series of novel 1,3,4-oxadiazole thioether derivatives (compounds 9-44) were designed and synthesized as potential inhibitors of thymidylate synthase (TS) and as anticancer agents. The in vitro anticancer activities of these compounds were evaluated against three cancer cell lines by the MTT method. Among all the designed compounds, compound 18 bearing a nitro substituent exhibited more potent in vitro anticancer activities with IC50 values of 0.7 ± 0.2, 30.0 ± 1.2, 18.3 ± 1.4 μM, respectively, which was superior to the positive control. In the further study, it was identified as the most potent inhibitor against two kinds of TS protein (for human TS and Escherichia coli TS, IC50 values: 0.62 and 0.47 μM, respectively) in the TS inhibition assay in vitro and the most potent antibacterial agents with MIC (minimum inhibitory concentrations) of 1.56-3.13 μg/mL against the tested four bacterial strains. Molecular docking and 3D-QSAR study supported that compound 18 can be selected as dual antitumor/antibacterial candidate in the future study.
- Du, Qian-Ru,Li, Dong-Dong,Pi, Ya-Zhou,Li, Jing-Ran,Sun, Jian,Fang, Fei,Zhong, Wei-Qing,Gong, Hai-Bin,Zhu, Hai-Liang
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p. 2286 - 2297
(2013/05/09)
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- Acylative cleavage of ethers with ZnCl2
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Acylative cleavage of common ether solvents with ZnCl2 was reported. Different substituted acyl chlorides were reacted with the common ether solvents in the presence of ZnCl2 to obtain the corresponding substituted benzoate.
- Yu, Yun-Feng,Gao, Jian-Rong,Jiang, Shao-Liang,Han, Liang,Jia, Jian-Hong,Li, Yu-Jin
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experimental part
p. 5199 - 5201
(2012/09/21)
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- Flavone-based novel antidiabetic and antidyslipidemic agents
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The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 70b, 90a, and 90b of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations. Published 2012 by the American Chemical Society.
- Verma, Alok K.,Singh, Himanshu,Satyanarayana, Mavurapu,Srivastava, Swayam P.,Tiwari, Priti,Singh, Amar B.,Dwivedi, Anil K.,Singh, Shio K.,Srivastava, Mukesh,Nath, Chandishwar,Raghubir, Ram,Srivastava, Arvind K.,Pratap, Ram
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supporting information; experimental part
p. 4551 - 4567
(2012/07/30)
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- Practical preparation of resveratrol 3-O-β-D-glucuronide
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A practical synthesis of resveratrol 3-Oβl-D-glucuronide, suitable for preparation of large quantities, was developed using selective deacetylation of resveratrol triacetate with ammonium acetate. A simplified procedure for large-scale preparation of resveratrol is also reported.
- Jungong, Christian S.,Novikov, Alexei V.
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p. 3589 - 3597,9
(2020/08/31)
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- A clean, palladium-catalyzed oxidative esterification of aldehydes using benzyl chloride
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A highly efficient, mild, simple and clean procedure is presented for the one-pot oxidation of aromatic and aliphatic aldehydes to their corresponding ethyl esters using benzyl chloride as the oxidant under palladium-catalyzed conditions. The reaction is complete in just 30 min under microwave irradiation and inert conditions are not required to obtain good to excellent yields (65-93%) of isolated products.
- Heropoulos, Georgios A.,Villalonga-Barber, Carolina
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experimental part
p. 5319 - 5322
(2011/10/31)
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- Synthesis, antimicrobial evaluation and QSAR studies of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides
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A series of 3-ethoxy-4-hydroxybenzylidene/4-nitrobenzylidene hydrazides (1-20) was synthesized and tested for in vitro antimicrobial activity. The results of antimicrobial studies indicated that the compounds having dinitro, methoxy, hydroxy and nitro substituents on phenyl ring of the aromatic acids were most active ones. The QSAR investigation indicated the importance of the topological parameter, third order molecular connectivity index ( 3χ) in describing the antimicrobial activity of synthesized hydrazides.
- Kumar, Davinder,Kapoor, Archana,Thangadurai, Ananda,Kumar, Pradeep,Narasimhan, Balasubramanian
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experimental part
p. 1293 - 1296
(2012/01/07)
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- Benzylidene/2-chlorobenzylidene hydrazides: Synthesis, antimicrobial activity, QSAR studies and antiviral evaluation
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A series of benzylidene hydrazides (1-20) was synthesized and tested, in vitro, for antibacterial, antifungal and antiviral activities. The microbial screening results indicated that compounds having chloro and nitro substituents were the most active ones. The antiviral evaluation depicted that compounds 9 and 19 were active against Vesicular stomatitis virus (VSV) in HeLa cell cultures. QSAR investigations indicated that the multi-target QSAR model was effective in describing the antimicrobial (antibacterial and antifungal) activity over the one-target QSAR models. Further the mt-QSAR model indicated that the topological parameters, second order molecular connectivity index (2χ) and third order Kier's alpha shape index (κα3) are effective in describing the antimicrobial activity of synthesized hydrazides.
- Kumar, Davinder,Judge, Vikramjeet,Narang, Rakesh,Sangwan, Sonia,De Clercq, Erik,Balzarini, Jan,Narasimhan, Balasubramanian
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experimental part
p. 2806 - 2816
(2010/08/20)
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- OXY SUBSTITUTED FLAVONES AS ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC AGENTS
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The present invention provides novel substituted flavone derivatives which exhibit anti- hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type ii diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.
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Page/Page column 14-15
(2010/11/08)
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- PLATINUM COMPLEX COMPOUNDS PRODUCTION THEREOF AND TREATMENT OF CANCER DISEASES
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The invention relates to novel platinum complex compounds, a method for production and use thereof in the treatment of cancer diseases.
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Page/Page column 23-24
(2010/02/12)
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- Effect of Organization of Zinc Porphyrin Hosts on Binding Enhancements and Recognition of Axial Ligands
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Two zinc porphyrin hosts, 2 and 3, containing an insufficiently preorganized binding pocket above each porphyrin plane have been synthesized and characterized.The binding behaviour of these hosts with various amine ligands as guests were examined spectrophotometrically in CHCl3 and were compared with that of a 'bis-roof' porphyrin zinc(II) complex, 1, which has a similar but fully preorganized binding pocket.The binding enhancements and shape selectivity revealed by 1 for saturated amines were almost diminished in 2 and 3.Proton NMR data showed that an induced fit of 2 for amine guests was incomplete probably owing to a weak driving force by non-polar host-guest interactions.Therefore, preorganization of the porphyrin hosts is indispensable to show recognition ability for amines in non-polar environments.The binding enhancemements that provide the recognition phenomenon for amine guests are attributed to the dispersion force between the porphyrin hosts and the amine guests.
- Imai, Hiroyasu,Uemori, Yoshio
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p. 1793 - 1798
(2007/10/02)
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- Long-chain Phenols. Part 16. A Novel Synthesis of Homologous Orsellinic Acids and their Methyl Ethers
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By the novel reaction of 3,5-dimethoxyfluorobenzene with n-alkyl-lithium compounds, followed by carbonation, homologous orsellinic acid dimethyl ethers (6-alkyl-2,4-dimethoxybenzoic acids) have been obtained.The reactions proceeded best with the homologues of methyl-lithium.These reactions are considered to occur by way of 3,5-dimethoxybenzyne. 2,4-Dimethoxyfluorobenzene did not form an aryne but gave 3-fluoro-2,6-dimethoxybenzoic acid instead.Decomposition with water of alkyl-lithium reaction mixtures from 3,5-dimethoxyfluorobenzene yielded 5-n-alkylresorcinol dimethyl ethers.Demethylaton of 6-alkyl-2,4-dimethoxybenzoic acids with boron trichloride proceeded partially and selectively to give the 6-alkyl-2-hydroxy-4-methoxybenzoic acids, and completely with aluminium chloride to give the homologous orsellinic acids.Boron tribromide was less effective, but readily gave the 5-alkyl resorcinols from the corresponding dimethyl ethers.
- Durrani, Aziz A.,Tyman, John H. P.
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p. 1658 - 1666
(2007/10/02)
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