- Diastereo- and Enantioselective Synthesis of Borylated 3-Hydroxyoxindoles by Addition of gem-Diborylalkanes to Isatins
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The catalytic asymmetric synthesis of borylated 3-hydroxyoxindoles by addition of gem-diborylalkanes to isatins is disclosed. Chiral 3-hydroxyoxindoles bearing two contiguous stereogenic centers were produced in up to >20:1 dr and 99% ee. The synthetic utility of the corresponding products is presented through several transformations of the boryl moiety. This report provides an efficient strategy to incorporate a boryl functional group toward the synthesis of 3-hydroxyoxindoles.
- Chen, Fen-Er,Li, Hong-Yan,Xiao, You-Cai,Xiong, Tong,Zhou, Li-Yan,Zhou, Yuan
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supporting information
p. 791 - 796
(2022/01/28)
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- One-pot method for preparing 9 - acridine formic acid
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The invention discloses a one-pot method for preparing 9 - acridine formic acid. After completion of the reaction, the unreacted oxalyl chloride and the reaction solvent are then distilled 5 - 10 °C off under reduced pressure until the reaction is complet
- -
-
Paragraph 0018-0051
(2021/11/10)
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- Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
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The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
- Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
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supporting information
p. 4302 - 4306
(2021/02/16)
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- Dynamic Kinetic Asymmetric Transformation of Racemic Diastereomers: Diastereo- and Enantioconvergent Michael–Henry Reactions to Afford Spirooxindoles Bearing Furan-Fused Rings
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Dynamic kinetic asymmetric transformation (DYKAT) reactions of racemic diastereomer mixtures that afford the products as essentially single diastereomers with high enantioselectivities are described. We demonstrated the DYKAT in the diastereo- and enantio
- Sohail, Muhammad,Tanaka, Fujie
-
supporting information
p. 21256 - 21260
(2021/08/23)
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- Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles
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An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.
- Ni, Qijian,Wang, Xuyang,Zeng, Da,Wu, Qianling,Song, Xiaoxiao
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supporting information
p. 2273 - 2278
(2021/04/05)
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- Applications of Ytterbium(II) Reagent as Grignard Reagent and Single-Electron Transfer Reagent in the Synthesis of 3-Substituted 2-Oxindoles
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The use of ytterbium(II) reagent as both nucleophilic reagent and single-electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent is reported. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for the preparation of 3-substituted 2-oxindoles was developed.
- Wang, Pengkai,Cao, Xuyan,Zhang, Songlin
-
supporting information
p. 3836 - 3846
(2021/07/02)
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- Palladium catalyzed divergent cycloadditions of vinylidenecyclopropane-diesters with methyleneindolinones enabled by zwitterionic π-propargyl palladium species
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A palladium-catalyzed divergent synthesis of spirooxindoles fused with a five- or a six-membered ring by a cycloaddition reaction of vinylidenecyclopropane-diesters with methyleneindolinones was disclosed. This protocol features anin situgenerated unprecedented zwitterionic π-propargyl palladium species in cycloaddition reactions and a switchable process between (3+2) and (4+2) cycloadditions by changing the phosphine ligand.
- Niu, Ben,Wei, Yin,Shi, Min
-
supporting information
p. 4783 - 4786
(2021/05/25)
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- Reaction of 1-substituted 3-(2-hydroxyethylamino)quinoline-2,4(1H,3H)-diones with isothiocyanic acid
-
[Figure not available: see fulltext.] 3-Chloroquinoline-2,4-diones react with ethanolamine to form 3-(3-hydroxyethylamino)quinoline-2,4-diones. These compounds afford, depending on substituents in positions 1 and 3, four different products from their reac
- Klásek, Antonín,Ly?ka, Antonín,Rouchal, Michal,Barto?ík, Radek
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p. 566 - 571
(2020/06/04)
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- Copper-Catalyzed Asymmetric Propargylic Alkylation with Oxindoles: Diastereo- A nd Enantioselective Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters
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A copper-catalyzed asymmetric propargylic alkylation of propargylic acetates with 3-substituted oxindoles for the stereoselective construction of vicinal tertiary and all-carbon quaternary stereocenters in a 3,3-disubstituted oxindole skeleton has been realized. The reaction proceeded smoothly under the catalysis of Cu(MeCN)4PF6combined with a chiral tridentate ferrocenyl P,N,N ligand, leading to a broad range of optically active 3,3-disubstituted oxindoles in high yields and with excellent diastereo- A nd enantioselectivities.
- Xia, Jin-Tao,Hu, Xiang-Ping
-
supporting information
p. 1102 - 1107
(2020/02/15)
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- Chiral naphthyl-C2-indole as scaffold for phosphine organocatalysis: Application in asymmetric formal [4 + 2] cycloaddition reactions
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The applications of a newly designed chiral naphthyl-C2-indole bifunctional phosphine organocatalyst in stereoselective formal [4 + 2] cycloaddition reactions were reported. The chiral naphthyl-C2-indole skeleton was introduced to bifunctional phosphine o
- He, Tingting,Peng, Lei,Li, Shan,Hu, Fangli,Xie, Chuandong,Huang, Shengli,Jia, Shiqi,Qin, Wenling,Yan, Hailong
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supporting information
p. 6966 - 6971
(2020/09/15)
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- Palladium-Catalyzed Cascade Hydrosilylation and Amino-Methylation of Isatin Derivatives
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We demonstrate that using palladium acetate as a catalyst for reduction of DMF and isatin derivatives by hydrosilanes, a cascade hydrosilylation and amino-methylation reaction can be realized. With DMF as a reactant and a solvent, the in-situ generated siloxymethylamine intermediate, an adduct of DMF and hydrosilanes, smoothly participates in the successive stages, providing a serials of Si, N-functionalized indolin-2-ones in moderate to good yields. This strategy exhibits high chemoselectivity toward carbonyl moieties reduction among the substrates. (Figure presented.).
- Liu, Yue,Xia, Yun-Tao,Cui, Su-Hang,Ji, Yi-Gang,Wu, Lei
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supporting information
p. 2632 - 2636
(2020/06/02)
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- Iodine-Catalyzed Aerobic Oxidation of Spirovinylcyclopropyl Oxindoles to Form Spiro-1,2-dioxolanes Diastereoselectively
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A novel method of iodine-catalyzed aerobic oxidation with spirovinylcyclopropyl oxindoles under mild conditions has been described. A series of spiro-1,2-dioxolanes were prepared in good to excellent yields and considerable diastereoselectivities. The new approach is operationally simple, scalable, and tolerant of various functional groups.
- Xiong, Cheng,Cheng, Kunpeng,Wang, Jiahua,Yang, Fulai,Lu, Jinrong,Zhou, Qingfa
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p. 9386 - 9395
(2020/08/14)
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- Efficient Synthesis of Spirooxindole Pyrrolones by a Rhodium(III)-Catalyzed C?H Activation/Carbene Insertion/Lossen Rearrangement Sequence
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A rhodium(III)-catalyzed domino annulation of simple olefins with diazo oxindoles to give spirooxindole pyrrolone products is described. This reaction can be formally viewed as the result of an anomalous tandem C?H activation, carbene insertion, Lossen rearrangement, and a nucleophilic addition process. The potential utility of this reaction was further demonstrated by the late-stage diversification of drug molecules.
- Ma, Biao,Wu, Peng,Wang, Xing,Wang, Zhengyu,Lin, Hai-Xia,Dai, Hui-Xiong
-
supporting information
p. 13335 - 13339
(2019/08/20)
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- Oxidative Radical Cyclization of N-methyl-N-arylpropiolamide to Isatins via Cleavage of the Carbon-carbon Triple Bond
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A radical cyclization of N-methyl-N-arylpropiolamide to isatins via an oxidative cleavage of a carbon-carbon triple bond has been developed. In the presence of oxone and NaNO2, a variety of N-methyl-N-arylpropiolamides were smoothly transformed into isatins. A nitration reaction proceeded along with the oxidative cyclization; both nitrated and non-nitrated isatins were obtained in a one-pot reaction with moderate to good total yields. This is the first example for the synthesis of isatins via the oxidative radical cleavage of a carbon-carbon triple bond. (Figure presented.).
- Liao, Yan-Yan,Gao, Yong-Chao,Zheng, Wenxu,Tang, Ri-Yuan
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p. 3391 - 3400
(2018/07/31)
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- NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy
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A new approach for the synthesis of isatins and isoindigoes by an inexpensive and environmentally friendly NaI-mediated transformation is disclosed. The selectivity could be switched by simply varying the solvent, and isatins (using THF) and isoindigoes (using DMSO) could be obtained in moderate to excellent yields.
- Zhang, Hong-Hua,Wang, Yong-Qiang,Huang, Long-Tao,Zhu, Long-Qing,Feng, Yi-Yue,Lu, Ying-Mei,Zhao, Quan-Yi,Wang, Xue-Qiang,Wang, Zhen
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supporting information
p. 8265 - 8268
(2018/07/29)
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- Syntheses of Acridones via Copper(II)-Mediated Relay Reactions from o-Aminoacetophenones and Arylboronic Acids
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The reaction of o-aminoacetophenones and arylboronic acids catalyzed by copper(II) salts in the presence of pyridine under an O2 atmosphere provides a general and efficient one-pot preparation of biologically interesting acridones. This relay reaction comprises an intermolecular Suzuki cross-coupling, intramolecular oxidative C(sp3)-H amination, and C(sp2)-H activation with simultaneous rearrangement of the generated isatin intermediates. This strategy tolerates both electron-donating and -withdrawing functionalities to afford various acridones in good to excellent yields.
- Wu, Hao,Zhang, Zhiguo,Liu, Qingfeng,Liu, Tongxin,Ma, Nana,Zhang, Guisheng
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supporting information
p. 2897 - 2901
(2018/05/29)
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- Synthesis of Indoline-2,3-diones by Radical Coupling of Indolin-2-ones with tert-Butyl Hydroperoxide
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A novel strategy has been developed for the synthesis of indoline-2,3-diones through a metal-free radical-coupling reaction. Alkyl radicals derived from indolin-2-ones through a radical-transfer reaction combine with the tert-butylhydroperoxy radical readily generated from commercially available tert-butyl hydroperoxide to afford 3-(tertbutylperoxy)indolin-2-one intermediates that can be further transformed into indoline-2,3-diones under air. This strategy provides a simple and e?cient route to the construction of a C=O bond without the use of any metal catalyst or base.
- Ying, Wei-Wei,Zhu, Wen-Ming,Liang, Hongze,Wei, Wen-Ting
-
supporting information
p. 215 - 218
(2017/09/28)
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- 2-Aminophenones, a common precursor to N-aryl isatins and acridines endowed with bioactivities
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Because N-arylation of isatin only worked with iodoferrocene (and in low yield), we employed N-arylation of 2-aminophenones and subsequent oxidative cyclization to access various N-arylated isatins. In the course of this work, we observed that N-arylation using 2-iodofuran, 2-iodobenzofuran and 2-iodobenzothiophene did not lead to the expected derivatives, but to (benzo)furo- and (benzo)thieno[2,3-b]quinolines. Separate cyclization was also performed under acidic conditions on 2-(arylamino)phenones in order to obtain acridines and related compounds. Most of the synthesized compounds were screened for their antiproliferative activity in A2058 melanoma cells, and against a panel of disease-relevant kinases such as mammalian CDK5/p25, PIM1, CLK1, DYRK1A, GSK3α/β Haspin and leishmanial CK1. The biological results are reported.
- Brikci-Nigassa, Nahida Mokhtari,Bentabed-Ababsa, Ghenia,Erb, William,Chevallier, Floris,Picot, Laurent,Vitek, Lucille,Fleury, Audrey,Thiéry, Valérie,Souab, Mohamed,Robert, Thomas,Ruchaud, Sandrine,Bach, Stéphane,Roisnel, Thierry,Mongin, Florence
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p. 1785 - 1801
(2018/03/12)
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- Cinchona-alkaloid-catalyzed enantioselective hydroxymethylation of 3-fluorooxindoles with paraformaldehyde
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Cinchona-alkaloid-catalyzed hydroxymethylation of 3-fluorooxindoles using paraformaldehyde as the C1 unit was achieved. A wide range of 3-fluorooxindoles was successfully reacted to give the corresponding 3-fluoro-3-hydroxymethyloxindoles with high efficiency and moderate to good enantioselectivity.
- Zhao, Jian-bo,Ren, Xinfeng,Zheng, Bu-quan,Ji, Jian,Qiu, Zi-bin,Li, Ya
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supporting information
p. 44 - 51
(2018/10/02)
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- Indole-2-ketone-3-spirobuprofezin or thiazolone compound and application thereof
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The invention discloses an indole-2-ketone-3-spirobuprofezin or thiazolone compound shown as a formula I or pharmaceutically acceptable salt thereof or a stereoisomer thereof and application thereof to preparation of a medicine for preventing and treating
- -
-
Paragraph 0131-0133
(2018/04/03)
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- Palladium-Catalyzed Oxidation of Indoles to Isatins by tert -Butyl Hydroperoxide
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The combination of a Pd catalyst and tert -butyl hydroeroxide (TBHP) is a powerful catalytic system for many types of oxidative transformations. Here, we report that a Pd/TBHP system facilitates the oxidation of indoles with a range of functionalities to give the corresponding isatin derivatives in good yields.
- Luo, Junfei,Gao, Shanshan,Ma, Yaorui,Ge, Guoping
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supporting information
p. 969 - 973
(2018/02/09)
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- Synthesis method of indole-2,3-dione compound
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The invention discloses a synthesis method of an indole-2,3-dione compound. The method comprises the following steps that a raw material as shown in a formula I is added into a Schlenk reactor, then acatalyst bis(acetonitrile)dichloropalladium (PdCl2(CH3CN)2), an oxidizing agent silver acetate (AgOAc) and a solvent methylbenzene are added, reaction is carried out under an oxygen atmosphere at 120-150 DEG C for 8-36 hours, a TLC board is used for monitoring the reaction, and after the reaction is carried out completely, the indole-2,3-dione compound as shown in a formula II is obtained throughpost-treatment.
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-
Paragraph 0030; 0037-0039
(2018/12/05)
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- Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid
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The invention discloses a method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid. The method comprises the following steps: a catalytic amount of catalyst copper iodide, indole, a derivative of the indole and peroxyacetic acid are added into a reaction vessel, wherein the indole, the derivative of the indole and the peroxyacetic acid are usedas raw materials, ethanol is used as a solvent, the reaction vessel is placed into a microwave reaction instrument, a reaction is performed at certain temperature and power, after a certain time, reduced-pressure concentration is performed, and a product is purified by column chromatography. The method provided by the invention is a method having novel raw materials, simple operation and high efficiency used for preparing a benzimidazole derivative; and compared with the prior art, the method provided by the invention has an obviously-accelerated reaction speed than that under conventional heating, mild reaction conditions, simple operation, a high yield, safety, low costs and environmental protection.
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-
Paragraph 0024; 0028
(2018/09/08)
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- Convenient and Clean Synthesis of Isatins by Metal-Free Oxidation of Oxindoles
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A metal-free synthesis of isatins was achieved through the oxidative reactions of oxindoles with molecular oxygen in the presence of tert -butyl nitrite as an additive. This strategy provides a convenient and simple synthetic route to the construction of C=O bonds without the need for any catalyst or base. The attractive features of this reaction include its convenient procedure and mild reaction conditions.
- Wei, Wen-Ting,Ying, Wei-Wei,Zhu, Wen-Ming,Wu, Yi,Huang, Yi-Ling,Cao, Yi-Qi,Wang, Yi-Ning,Liang, Hongze
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supporting information
p. 2307 - 2310
(2017/10/06)
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- Preparation method of isatin derivatives
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The invention discloses a novel method for synthesizing isatin derivatives. According to the method, a catalytic oxidation system of tert-butyl nitrite/O2 is adopted without using metal reagents, reaction is performed at room temperature under normal pressure, and isatin derivatives are obtained with high yield and high purity. The method has the advantages of simple technical operation process and low cost.
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-
Paragraph 0043; 0044; 0045
(2017/10/27)
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- Active sp3 C-H Bond Oxidation Initiated sp3-sp2 Consecutive C-H Functionalization of N-Arylglycine Amides: Construction of Isatins
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In the presence of catalytic triarylamine radical cation, an sp3-sp2 consecutive C-H functionalization of N-arylglycine amides was achieved, providing a series of isatin derivatives in high yields. In this transformation, the initial aerobic oxidation of the relatively active sp3 C-H bonds triggered the following intramolecular cyclization, in which the aniline group was employed as a removable auxiliary group to enable the consecutive process.
- Ji, Honghe,Zhu, Yingzu,Shao, Yu,Liu, Jing,Yuan, Yu,Jia, Xiaodong
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p. 9859 - 9865
(2017/09/23)
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- Isatin derivative and synthetic method thereof
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The invention relates to an isatin derivative and a synthetic method thereof. The synthetic method comprises the following steps: adding N-substituted indolinone into a solvent first, then adding an oxidant, and performing a reaction in an oil bath at 90-140 DEG C until a reaction system changes from clear liquid into reddish brown liquid;removing the solvent from the reaction system to obtain a crude product, performing extraction and separation on the crude product sequentially to obtain the isatin derivative. In the synthetic method provided by the invention, the N-substituted indolinone is used as a raw material and contains a methylene in a molecule, and a phenyl at a position adjacent to the methylene, so that under the action of the oxidant, the benzyl methylene can form a stable intermediate more possibly, and by matching with reaction temperature control, N-phenyl indolinone is oxidized into a target product namely the isatin derivative under the action of the oxidant, byproducts are effectively reduced, and finally the isatin derivative is purified by extraction and separation. The isatin derivative provided by the invention has a simple synthesis route, the steps are simplified, the generation of the byproducts is effectively avoided, an atom efficiency is fully utilized, and the yield of the isatin derivative is improved.
- -
-
Paragraph 0032-0036; 0038; 0039
(2017/08/29)
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- Electrocatalytic C-H/N-H Coupling of 2′-Aminoacetophenones for the Synthesis of Isatins
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2′-Aminoacetophenones undergo a C(sp3)-H oxidation followed by intramolecular C-N bond formation by virtue of a simple electrochemical oxidation in the presence of n-Bu4NI, providing various isatins with moderate to good yields. The reaction intermediates were detected, and a radical-based pathway was proposed.
- Qian, Peng,Su, Ji-Hu,Wang, Yukang,Bi, Meixiang,Zha, Zhenggen,Wang, Zhiyong
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p. 6434 - 6440
(2017/06/23)
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- Chan-Lam-Type C-N Cross-Coupling Reactions under Base- and Ligand-Free CuI-Zeolite Catalysis
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Various representative copper(I)-exchanged zeolites were investigated for their catalytic potential in Chan-Lam cross-coupling reactions. CuI-USY appeared as the best catalyst and proved to efficiently promote C-N cross-coupling processes under attractive, simple, and practical conditions, namely refluxing in methanol under air and without any base.
- Garnier, Tony,Sakly, Randa,Danel, Mathieu,Chassaing, Stefan,Pale, Patrick
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supporting information
p. 1223 - 1230
(2017/03/11)
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- Cu-catalyzed oxidation of indoles to isatins
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The first example of Cu-catalyzed oxidation of indoles to isatin derivatives by the use of cheap aqueous tert-butyl peroxide as an oxidant was developed. This methodology is practically convenient and highly functional group tolerant, allowing a variety of indole derivatives to transform into the corresponding isatin derivatives in good yields.
- Luo, Junfei,Zhao, Yanchao,Xu, Xing,Zheng, Junliang,Liang, Hongze
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supporting information
p. 4591 - 4594
(2017/11/15)
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- Synthesis and bio-evaluation of quaternary centered 3-hydroxy-3-(trifluoromethyl)indolin-2-one derivatives for anticancer and antimicrobial activities
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Abstract: A series of C(3)-trifluoromethylated compounds derived from N-substituted isatins were synthesized. The biological activity of all 3-hydroxy-3-(trifluoromethyl)indolin-2-one derivatives have been evaluated for in vitro cytotoxic activity and antibacterial activity. The active compounds were screened against nuclear xenobiotic receptor CAR (PDB ID: 1XLS), PIM1 kinase (PDB ID: 2O65), and CDK2 kinase (PDB ID: 3QHR) by using in silico molecular docking studies to obtain lead molecules. In addition to its potential anticancer activity, 5-bromo-3-ethynyl-3-hydroxy-1-(prop-2-yn-1-yl)indolin-2-one also showed specific antibacterial activity against S. aureus. Graphical abstract: [Figure not available: see fulltext.]
- Bikshapathi, Raktani,Prathima, Parvathaneni Sai,Yashwanth,Pamanji,Jagadeeshkumar,Maheshwari,Rao, J. Venkateswara,Murty,Rao, V. Jayathirtha
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p. 757 - 764
(2017/03/17)
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- Rhodium(II)-catalyzed direct sulfenylation of diazooxindoles with disulfides
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Rhodium(ii)-catalyzed direct sulfenylation of diazooxindoles using disulfides as the sulfenylating agent was developed via intermolecular C-S bond formation. This novel protocol provides a rapid synthetic route to 3-alkylthiooxindoles, 3,3-dialkylthiooxindoles, or 3,3-diarylthiooxindoles in moderate to good yield. The transformation is proposed to proceed through sulfur ylide formation followed by S-S bond cleavage and rearrangement.
- Khanal, Hari Datta,Kim, Sung Hong,Lee, Yong Rok
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p. 58501 - 58510
(2016/07/07)
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- Framework-Copper-Catalyzed C?N Cross-Coupling of Arylboronic Acids with Imidazole: Convenient and Ligand-Free Synthesis of N-Arylimidazoles
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A convenient and environmentally benign synthesis of N-arylimidazoles has been demonstrated by a straightforward reaction catalyzed by the unsaturated coordination sites of Cu in the copper terephthalate metal–organic framework (Cu(tpa)-MOF). A series of N-arylimidazoles has been synthesized in excellent yields by the C?N cross-coupling reaction of arylboronic acids and imidazoles catalyzed by the Cu(tpa)-MOF using ethanol as a benign solvent. The present ligand-free catalytic system proceeds smoothly under mild conditions, avoids stoichiometric Cu reagents, tolerates many functional groups, has a wide substrate scope, and is feasible with other nitrogen heterocycles. The stability and heterogeneity of the catalyst is evidenced by the results of a heterogeneity test, and the catalyst can be reused several times without a loss of activity. The easy preparation of the catalyst, its stability, recovery by simple filtration, and reusability reveal Cu(tpa) MOF as a versatile catalyst for academic and industrial applications.
- Devarajan, Nainamalai,Suresh, Palaniswamy
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p. 2953 - 2960
(2016/09/28)
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- Design, synthesis and evaluation of N-aryl-glyoxamide derivatives as structurally novel bacterial quorum sensing inhibitors
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Bacteria cooperatively regulate the expression of many phenotypes through a mechanism called quorum sensing (QS). Many Gram-negative bacteria use an N-acyl homoserine lactone (AHL)-mediated QS system to control biofilm formation and virulence factor production. In recent years, quorum sensing inhibitors (QSIs) have become attractive tools to overcome antimicrobial resistance exhibited by various pathogenic bacteria. In the present study, we report the design and synthesis of novel N-arylisatin-based glyoxamide derivatives via the ring-opening reaction of N-aryl isatins with cyclic and acylic amines, and amino acid esters. The QSI activity of the synthesized compounds was determined in the LasR-expressing Pseudomonas aeruginosa MH602 and LuxR-expressing Escherichia coli MT102 reporter strains. Compounds 31 and 32 exhibited the greatest QSI activity in P. aeruginosa MH602, with 48.7% and 42.7% reduction in QS activity at 250 μM, respectively, while compounds 31 and 34 showed 73.6% and 43.7% QSI activity in E. coli MT102. In addition, the ability of these compounds to inhibit the production of pyocyanin in P. aeruginosa (PA14) was also determined, with compound 28 showing 47% inhibition at 250 μM. Furthermore, computational docking studies were performed on the LasR receptor protein of P. aeruginosa, which showed that formation of a hydrogen bonding network played a major role in influencing the QS inhibitory activity. We envisage that these novel non-AHL glyoxamide derivatives could become a new tool for the study of QS and potentially for the treatment of bacterial infections.
- Nizalapur, Shashidhar,Kimyon, ?nder,Biswas, Nripendra Nath,Gardner, Christopher R.,Griffith, Renate,Rice, Scott A.,Manefield, Mike,Willcox, Mark,Black, David StC.,Kumar, Naresh
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p. 680 - 693
(2016/01/12)
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- Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch
-
An efficient chemodivergent strategy for visible light photocatalysis is developed. In the presence of a dicyanopyrazine-derived chromophore (DPZ) photocatalyst, aerobic photooxygenation of indoles could produce either isatins or formylformanilides in satisfactory yields by judiciously selecting inorganic salts or modulating the reaction pH. The current chemodivergent method is also effective with 2-substituted indoles, opening straightforward synthetic routes to valuable 2,2-disubstituted 3-oxindoles, formylformanilide derivatives, and benzoxazinones. Mechanistic investigations involving cyclic voltammetry studies further confirm that reaction pH influences the electrochemical properties of DPZ, thus affecting the oxidative pathway by which indoles are being transformed.
- Zhang, Chenhao,Li, Sanliang,Bure?, Filip,Lee, Richmond,Ye, Xinyi,Jiang, Zhiyong
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p. 6853 - 6860
(2016/10/18)
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- Iodine-Catalyzed Oxidation of N-Substituted Indoles by using Chloramine-B: A Facile and Practical Approach to Isatins
-
An efficient method for the iodine-catalyzed oxidation of N-substituted indoles by using chloramine-B under mild reaction conditions was explored. This reaction was found to be tolerant to a variety of functional groups and provided the corresponding isatins in moderate to excellent yields. In addition, application of this method to the one-pot synthesis of 3-hydroxyoxindole and N-methylisatin oxime was realized.
- Liu, Peijun,Guo, Jiajing,Wei, Wentao,Liu, Xiaozu,Sun, Pinghua
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supporting information
p. 2105 - 2109
(2016/05/09)
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- Palladium(0)-catalyzed single and double isonitrile insertion: A facile synthesis of benzofurans, indoles, and isatins
-
A palladium(0)-catalyzed cascade process consisting of isonitrile insertion and ?±-Csp3-H cross-coupling can be achieved for the synthesis of benzofurans and indoles. The construction of isatins by a Pd-catalyzed cascade reaction incorporating double isonitrile insertion, amination, and hydrolysis has also been achieved. The key features of this work include diverse heterocycle synthesis, phosphine-ligand-free reaction conditions, a one-pot procedure, simple and commercially available starting materials, broad functional-group compatibility, and moderate to good reaction yields.
- Senadi, Gopal Chandru,Hu, Wan-Ping,Boominathan, Siva Senthil Kumar,Wang, Jeh-Jeng
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p. 998 - 1003
(2015/02/05)
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- Air-stable palladium(0) phosphine sulfide catalysts for Ullmann-type C-N and C-O coupling reactions
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This paper describes an efficient procedure for palladium(0)-catalyzed N-arylation and O-arylation of aryl halides by Ullmann-type cross coupling reaction under mild reaction conditions in a short reaction time. Two phosphine sulphide ligands and their corresponding Pd(0) complexes namely [Pd(p2S2)(dba)] and [Pd(pp3S4)(dba)], were synthesized, where p2S2 is 1,2-bis(diphenylphosphino)ethane disulfide, pp3S4 is tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide and dba is dibenzylideneacetone. Optimal reaction conditions were determined for the arylation reactions using iodobenzene and benzimidazole by varying temperature, solvent, base and catalyst loading. The cross coupling reactions were carried out taking iodobenzenes/bromobenzenes and a wide variety of substituted aryl amines/phenols/alcohols with different steric and electronic properties to afford the desired N-aryl amines/diaryl ethers/alkyl aryl ethers in good to excellent yield (70-94%).
- Majumder, Arpi,Gupta, Ragini,Mandal, Mrinmay,Babu, Madhu,Chakraborty, Debashis
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- Cyclization of cyanoethylated ketones as a route to 6-substituted indole derivatives
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δ-Cyanoketones are quickly cyclized with KOtBu to 3-aminocyclohex-2-enone derivatives, which in turn will give substituted indoles when treated with oxalyl chloride. Thus, 3-amino-6,6-dimethylcyclohex-2-enone gave 3-chloro-6,6-dimethyl-2,5,6,7-tetrahydroindole-2,5-dione, whose structure was corroborated by X-ray crystallography, whereas the corresponding molecule without the blocking gem-dimethyl groups, 3-aminocyclohex-2-enone, gave via hydrogen shifts 6-chloro-3-hydroxyoxindole.
- Bergman, Jan,Stensland, Birgitta
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- Design, synthesis and biological evaluation of N-alkyl or aryl substituted isoindigo derivatives as potential dual cyclin-dependent kinase 2 (CDK2)/glycogen synthase kinase 3β (GSK-3β) phosphorylation inhibitors
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A series of N-alkyl or aryl substituted isoindigo derivatives have been synthesized and their anti-proliferative activity was evaluated by Sulforhodamine B (SRB) assay. Some of the target compounds exhibited significant antitumor activity, including compounds 6h and 6k (against K562 cells), 6i (against HeLa cells) and 6j (against A549 cells). N-(p-methoxy-phenyl)-isoindigo (6k) exhibited a high and selective anti-proliferative activity against K562 cells (IC50 7.8 μM) and induced the apoptosis of K562 cells in a dose-dependent manner. Compound 6k arrested the cell cycle at S phase in K562 cells by decreasing the expression of cyclin A and CDK2, which played critical roles in DNA replication and passage through G2 phase. Moreover, compound 6k down-regulated the expression of p-GSK-3β (Ser9), β-catenin and c-myc proteins, up-regulated the expression of GSK-3β, consequently, suppressed Wnt/β-catenin signaling pathway and induced the apoptosis of K562 cells. The binding mode of compound 6k with GSK-3β was simulated using molecular docking tools. All of these studies gave a better understanding to the molecular mechanisms of this class of agents and clues to develop dual CDK2/GSK-3β (Ser9) phosphorylation inhibitors applied in cancer chemotherapy.
- Zhao, Ping,Li, Yanzhong,Gao, Guangwei,Wang, Shuai,Yan, Yun,Zhan, Xiaoping,Liu, Zenglu,Mao, Zhenmin,Chen, Shaoxiong,Wang, Liqun
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p. 165 - 174
(2014/09/17)
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- Copper-catalyzed aerobic oxidative annulation and carbon-carbon bond cleavage of arylacetamides: Domino synthesis of fused quinazolinones
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An efficient copper-catalyzed tandem aerobic oxidative annulation and carbon-carbon bond cleavage reaction was developed from easily accessible arylacetamides, which provides a direct approach for the domino synthesis of a vast array of tricyclic or tetracyclic fused quinazolinone alkaloid structures. A plausible reaction mechanism is proposed involving an aerobic benzylic oxidation/ cyclization/decarbonylation cascade.
- Sun, Jie,Tan, Qitao,Yang, Wusong,Liu, Bingxin,Xu, Bin
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p. 388 - 394
(2014/05/20)
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- Copper-catalyzed intramolecular oxidative C(sp3)-H amidation of 2-aminoacetophenones: Efficient synthesis of indoline-2,3-diones
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An efficient synthesis of diverse indoline-2,3-diones from 2-aminoacetophenones through copper-catalyzed intramolecular C(sp3)-H amidation is developed. The reaction proceeds in DMSO by using O2 as the sole oxidant to provide the desired products in moderate to good yields.
- Huang, Jinbo,Mao, Tingting,Zhu, Qiang
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p. 2878 - 2882
(2014/05/20)
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- Ylide mediated carbonyl homologations for the preparation of isatin derivatives
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An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protection of the amine or chromatographic isolation of the intermediate ylide. Gentle oxidation of the sulfur ylides provides isatin derivatives with N-H, N-alkyl, N-aryl substitution, electron-rich and electron-poor aromatic rings, and heterocyclic aromatic systems. We anticipate that this method will greatly expand the accessibility of complex isatin derivatives.
- Lollar, Christina T.,Krenek, Katherine M.,Bruemmer, Kevin J.,Lippert, Alexander R.
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supporting information
p. 406 - 409
(2014/01/06)
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- Logical design and synthesis of indole-2,3-diones and 2-hydroxy-3(2H)- benzofuranones via one-pot intramolecular cyclization
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A novel and attractive protocol to synthesis indole-2,3-diones and 2-hydroxy-3(2H)-benzofuranones and via copper(II) oxide catalyzed intramolecular cyclization is described. This method possesses functional-group compatibility, easy workup procedure, shorter reaction time and high yields.
- Gao, Fang-Fang,Xue, Wei-Jian,Wang, Jun-Gang,Wu, An-Xin
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p. 4331 - 4335
(2014/06/10)
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- An efficient route to synthesize isatins by metal-free, iodine-catalyzed sequential C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones
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A novel molecular I2-catalyzed synthesis of isatins through C(sp3)-H oxidation and intramolecular C-N bond formation of 2′-aminoacetophenones with excellent yields up to 97% under transition metal, base, additive, peroxide and ligand free conditions is described. The present protocol is suitable for gram scale synthesis of isatins and retained its high yield. Further, the synthetic utility of this present reaction towards synthesis of bioactive 3-hydroxy-2-oxindoles and oxindoles is demonstrated. This journal is
- Rajeshkumar, Venkatachalam,Chandrasekar, Selvaraj,Sekar, Govindasamy
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p. 8512 - 8518
(2014/12/10)
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- Direct amidation of 2'-aminoacetophenones using I2-TBHP: A unimolecular domino approach toward isatin and iodoisatin
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Synthesis of isatin and iodoisatin from 2'-aminoacetophenone was achieved via oxidative amido cyclization of the sp3 C-H bond using I 2-TBHP as the catalytic system. The reaction proceeds through sequential iodination, Kornblum oxidation, and amidation in one pot. This method is simple, atom economic, and works under metal- and base-free conditions.
- Ilangovan, Andivelu,Satish, Gandhesiri
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p. 4984 - 4991
(2014/06/23)
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- Discovery and structure optimization of a series of isatin derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors
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In this study, the crystal structure of the Mycobacterium tuberculosis (MTB) enzyme chorismate mutase (CM) bound to transition state analogue (PDB: 2FP2) was used as a framework for virtual screening of the BITS-Pilani in-house database (2500 compounds) to identify new scaffold. We identified isatin as novel small molecule MTB CM inhibitors; further twenty-four isatin derivatives were synthesized and evaluated in vitro for their ability to inhibit MTB CM, and activity against M. tuberculosis as steps towards the derivation of structure-activity relationships (SAR) and lead optimization. Compound 3-(4-nitrobenzylidene)indolin-2-one, 24 emerged as the most promising lead with an IC50 of 1.01 ± 0.22 μm for purified CM and MIC of 23.5 μm for M. tuberculosis, with little or no cytotoxicity. 2D interaction profile of compounds 1, 7 and 25 with the active site residues.
- Jeankumar, Variam U.,Alokam, Reshma,Sridevi, Jonnalagadda P.,Suryadevara, Priyanka,Matikonda, Siddharth S.,Peddi, Santosh,Sahithi, Seedarala,Alvala, Mallika,Yogeeswari, Perumal,Sriram, Dharmarajan
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p. 498 - 506
(2014/05/06)
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- Synthesis of isatins by I2/TBHP mediated oxidation of indoles
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An I2/TBHP mediated oxidation of commercially available indoles has been developed, which affords isatins in moderate to good yields.
- Zi, You,Cai, Zhong-Jian,Wang, Shun-Yi,Ji, Shun-Jun
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supporting information
p. 3094 - 3097
(2014/06/23)
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- Selenium-promoted intramolecular oxidative amidation of 2-(arylamino)acetophenones for the synthesis of N-arylisatins
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A convenient method for the synthesis of N-arylisatins from 2-(arylamino)acetophenones by using SeO2 as an oxidant is described. Various substituted N-arylisatins were selectively obtained in good to excellent yields. The reaction tolerates a wide range of functionalities. Copyright
- Liu, Yong,Chen, Hui,Hu, Xiong,Zhou, Wang,Deng, Guo-Jun
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p. 4229 - 4232
(2013/07/26)
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- Copper-mediated selective C-H activation and cross-dehydrogenative C-N coupling of 2′-aminoacetophenones
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Isatins were obtained by cross-dehydrogenative C-N annulation and dealkylative C-N annulation of 2′-N-aryl/alkylaminoacetophenones and 2′-N,N-dialkylaminoacetophenones respectively in the presence of Cu(OAc)2·H2O/NaOAc/air. However, on reaction with CuBr, 2′-N-benzylaminoacetophenones underwent selective oxidation of an α-methylene group of amine rather than the 2-acetyl group to provide corresponding benzamides exclusively. Base played an important role in selective oxidation by lowering the temperature and time.
- Ilangovan, Andivelu,Satish, Gandhesiri
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supporting information
p. 5726 - 5729
(2013/12/04)
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