- Unusual phenomena during the resolution of 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ): Thermodynamic-kinetic control
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6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ) was resolved in several different solvents by tartaric acid derivatives as the most common acidic resolving agents available in industrial quantities. Strong reaction kinetics and solvent dependence wer
- Balint, Jozsef,Egri, Gabriella,Kiss, Violetta,Gajary, Antal,Juvancz, Zoltan,Fogassy, Elemer
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Read Online
- Synthesis and antifungal activity of diverse C-2 pyridinyl and pyridinylvinyl substituted quinolines
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Diverse 2-pyridinyl quinolines 6-12 and 2-pyridinilvinyl quinolines 13-17 were prepared using a straightforward synthesis based on the BiCl 3-catalyzed multicomponent imino Diels-Alder (imino DA) reaction or a novel tandem imino DA/catalytic tetrahydroquinoline ring oxidation/Perkin condensation sequential process. All members of the series showed activities against dermatophytes and some of them possessed a broad spectrum of action. 2-(Pyridin-4-yl)quinoline 9 and 2-(2-pyridin-4-yl)vinyl)quinoline 16 showed the best MIC80 and MIC50 against the clinically important fungi Candida albicans and non-albicans Candida species. In turn, 6-ethyl-2-(pyridin-2-yl)quinoline 6 showed the best properties against standardized as well as clinical strains of Cryptococcus neoformans.
- Kouznetsov, Vladimir V.,Melendez Gomez, Carlos M.,Derita, Marcos G.,Svetaz, Laura,Zacchino, Susana A.,Del Olmo, Esther
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Read Online
- Rhodium-Catalyzed C-H Annulation of Free Anilines with Vinylene Carbonate as a Bifunctional Synthon
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Chemical transformation with vinylene carbonate as an emerging synthetic unit has recently attracted considerable attention. This report is a novel conversion pattern with vinylene carbonate, in which such a vibrant reagent unprecedentedly acts as a difunctional coupling partner to complete the C-H annulation of free anilines. From commercially available substrates, this protocol leads to the rapid construction of synthetically versatile 2-methylquinoline derivatives (43 examples) with excellent functionality tolerance.
- Nan, Jiang,Yin, Jiacheng,Gong, Xue,Hu, Yan,Ma, Yangmin
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supporting information
p. 8910 - 8915
(2021/11/24)
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- Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen
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The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.
- Wei, Lanfeng,Wei, Yu,Xu, Liang,Zhang, Jinli
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supporting information
p. 4446 - 4450
(2021/06/30)
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- Cooperative Lewis Acid Catalysis for the Enantioselective C(sp3)-H Bond Functionalizations of 2-Alkyl Azaarenes
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Herein, we describe the enantioselective C(sp3)-H bond functionalizations of 2-alkyl azaarenes using a cooperative dual Lewis acid catalysis. An achiral Lewis acid activates the unactivated azaarene partner without the need for a strong base. Orthogonally, a chiral-at-metal Lewis acid catalyst enables LUMO lowering and induces chirality. This method tolerates a range of complex molecular scaffolds and exhibits good to excellent yields and selectivity while accepting a wide variety of functional groups.
- Rai, Pramod,Waiba, Satyadeep,Maji, Kakoli,Sahoo, Dibyaranjan,Maji, Biplab
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supporting information
p. 8888 - 8893
(2021/11/24)
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- Half-Sandwich Ruthenium Complexes for One-Pot Synthesis of Quinolines and Tetrahydroquinolines: Diverse Catalytic Activity in the Coupled Cyclization and Hydrogenation Process
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Four types of half-sandwich ruthenium complexes with an N,O-coordinate mode based on hydroxyindanone-imine ligands have been prepared in good yields. These stable ruthenium complexes exhibited high activity in the catalytic synthesis of quinolines from the reactions of amino alcohols with different types of ketones or secondary alcohols under very mild conditions. Moreover, the methodology for the direct one-pot synthesis of tetrahydroquinoline derivatives from amino alcohols and ketones has been also developed on the basis of the continuous catalytic activity of this ruthenium catalyst in the selective hydrogenation of the obtained quinoline derivatives with a low catalyst loading. The corresponding products, quinolines and tetrahydroquinoline derivatives, were afforded in good to excellent yields. The efficient and diverse catalytic activity of these ruthenium complexes suggested their potential large-scale application. All of the ruthenium complexes were characterized by various spectroscopies to confirm their structures.
- Yun, Xue-Jing,Zhu, Jing-Wei,Jin, Yan,Deng, Wei,Yao, Zi-Jian
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supporting information
p. 7841 - 7851
(2020/06/04)
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- Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation
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The α7 nicotinic acetylcholine receptor (α7 nAChR) has emerged as a promising therapeutic target for schizophrenia. In our previous work, a novel series of α7-nAChR agonists bearing scaffold of indolizine were discovered. To explore the effect of aromaticity on the activity and find more active agents, herein, fused heterocyclic carboxamide derivatives were designed and synthesized in this study. Based on the evaluation by two-electrode voltage clamp in Xenopus oocytes, 27 of the synthesized compounds showed obvious agonism of α7 nAChR. Particularly, compounds 10a and 10e showed significantly higher Emax than EVP-6124. The result illustrated the importance of aromaticity to the activity of agonism. Compound 10a, which showed EC50 of 1.88 μM and Emax of 72.4%, was further characterized comprehensively, including co-application with type II positive allosteric modulator PNU-120596, selectivity with other closely related ligand-gated ion channel, etc. The results showed that 10a showed moderate selectivity over other subtypes such as α4β2 and α3β4 nAChR. 10a evoked α7-like currents that were inhibited by MLA and enhanced in the presence of the α7 PAM PNU-120596. The analysis of binding mode and understanding of structure-activity relationship provided insights to develop more potent novel α7-nAChR agonists.
- Xue, Yu,He, Xiaomeng,Yang, Taoyi,Wang, Yuxi,Liu, Zhenming,Zhang, Guisen,Wang, Yanxing,Wang, Kewei,Zhang, Liangren,Zhang, Lihe
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- Deracemization of Phenyl-Substituted 2-Methyl-1,2,3,4-Tetrahydroquinolines by a Recombinant Monoamine Oxidase from Pseudomonas monteilii ZMU-T01
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A monoamine oxidase (MAO5) from Pseudomonas monteilii ZMU-T01 was first heterologously expressed in Escherichia coli BL21(DE3) and then used as a biocatalyst for the deracemization of racemic 2-methyl-1,2,3,4-tetrahdroquinoline derivatives to yield the unreacted R enantiomer with up to >99 % ee. Sequence alignment revealed that MAO5 shared 14.7 % identity toward the well-studied monoamine oxidase (MAO-N).
- Deng, Guozhong,Wan, Nanwei,Qin, Lei,Cui, Baodong,An, Miao,Han, Wenyong,Chen, Yongzheng
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p. 2374 - 2377
(2018/04/19)
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- Acceptorless Dehydrogenation of N-Heterocycles and Secondary Alcohols by Ru(II)-NNC Complexes Bearing a Pyrazoyl-indolyl-pyridine Ligand
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Ruthenium(II) hydride complexes bearing a pyrazolyl-(2-indol-1-yl)-pyridine ligand were synthesized and structurally characterized by NMR analysis and X-ray single crystal crystallographic determinations. These complexes efficiently catalyzed acceptorless dehydrogenation of N-heterocycles and secondary alcohols, respectively, exhibiting highly catalytic activity with a broad substrate scope. The present work has established a strategy to construct highly active transition metal complex catalysts and provides an atom-economical and environmentally benign protocol for the synthesis of aromatic N-heterocyclic compounds and ketones.
- Wang, Qingfu,Chai, Huining,Yu, Zhengkun
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p. 584 - 591
(2018/03/08)
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- Blue-light-promoted carbon-carbon double bond isomerization and its application in the syntheses of quinolines
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A blue-light-promoted carbon-carbon double bond isomerization in the absence of any photoredox catalyst is reported. It provides rapid access to a series of quinolines in good to excellent yields under simple aerobic conditions. The protocol is direct, catalyst-free and operationally convenient.
- Chen, Xinzheng,Qiu, Shuxian,Wang, Sasa,Wang, Huifei,Zhai, Hongbin
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supporting information
p. 6349 - 6352
(2017/08/10)
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- H-phosphonate mediated sulfonylation of 2-substituted quinoline N-oxides: One-pot strategy for the synthesis of 3/4-sulfonylquinoline derivatives
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series of biologically important 3/4-sulfonylquinoline derivatives was synthesized starting from easily available sodium benzenesulfinates, diethyl H-phosphonate and 2-substituted quinoline N-oxides in onepot under metal-free conditions. H-phosphonate plays a decisive role in activating the C3-H, C4-H bonds of the 2-substituted quinoline N-oxides. The isolated 3/4-sulfonylquinolines were characterized by 1H, 13CNMR spectroscopy and HR MS.
- Ma, Huili,Liu, Shuyun,Zhu, Shaohua,Bi, Wenzhu,Chen, Xiaolan,Zhao, Yufen
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supporting information
p. 887 - 895
(2017/08/15)
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- Oxidative Addition Complexes as Precatalysts for Cross-Coupling Reactions Requiring Extremely Bulky Biarylphosphine Ligands
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In this report, we describe the application of palladium-based oxidative addition complexes (OACs) as effective precatalysts for C-N, C-O, and C-F cross-coupling reactions with a variety of (hetero)arenes. These complexes offer a convenient alternative to previously developed classes of precatalysts, particularly in the case of the bulkiest biarylphosphine ligands, for which palladacycle-based precatalysts do not readily form. The precatalysts described herein are easily prepared and stable to long-term storage under air.
- Ingoglia, Bryan T.,Buchwald, Stephen L.
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supporting information
p. 2853 - 2856
(2017/06/07)
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- Assembly of Diversely Substituted Quinolines via Aerobic Oxidative Aromatization from Simple Alcohols and Anilines
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An aerobic oxidative aromatization of simple aliphatic alcohols and anilines under the Pd(OAc)2/2,4,6-Collidine/Br?nsted acid catalytic system has been established, providing a direct approach for the preparation of diverse substituted quinoline derivatives in high yields with wide functional group tolerance. Practically, the protocol can be easily scaled up to gram-scale and was utilized in the concise formal synthesis of a promising herbicide candidate.
- Li, Jixing,Zhang, Jinlong,Yang, Huameng,Jiang, Gaoxi
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supporting information
p. 3284 - 3290
(2017/03/23)
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- Preparation method of quinoline derivative
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The invention provides a preparation method of a quinoline derivative. The method includes the steps of: in the presence of an oxidizing agent, adding a catalyst, then adding aniline or aromatic amine with different substituents, at the same time adding alcohol for reaction so as to prepare the quinoline derivative by one step. Specifically, the catalyst comprises a metal catalyst, an assistant catalyst I and an assistant catalyst II; the metal catalyst is a transition metal catalyst; the assistant catalyst I is an alkaline nitrogen-containing ligand; and the assistant catalyst II is an acidic compound. The quinoline derivative prepared by the method provided by the invention has stable performance and high purity. And the preparation method of the quinoline derivative can prepare quinoline, 2-methylquinoline, 8-hydroxyquinoline quinoline and other derivatives by one-step reaction, and the preparation method is simple and practicable. The preparation process does not produce new "three wastes", is environment-friendly, and provides a green and environment-friendly synthesis method. The preparation method has the characteristics of few raw material variety, little reaction equipment, few preparation step and low cost, and is more suitable for industrial production.
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Paragraph 0073; 0074
(2017/06/02)
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- Synthesis and structure elucidation of allyl Pd(II) complexes of NHC ligands derived from substituted imidazo[1,5-a]quinolin-1(2H)-ylidene
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Nine Pd(II) complexes involving N-heterocyclic carbenes (NHCs) derived from 2-substituted and 2- and 7-substituted imidazo[1,5-a]quinolin-1(2H)-ylidene with auxiliary allylic ligands were synthesized and characterized. The structure and configuration of the complexes were elucidated on the basis of combination of dynamic NMR and DFT studies. Conformational studies in respect of hindered rotation around Pd-C bond and η3-η1-η3 pseudo allyl rotation were performed. The results from dynamic NMR and DFT studies confirmed the mechanism of selective η3-η1-η3 isomerization, whose energy barriers are affected by steric hindrance of substituents at nitrogen atom. Energy barriers of isomerization (16.7–18.8 kcal/mol) are slightly influenced by the electronic nature of substituents at seventh position in imidazo[1,5-a]quinolin-1(2H)-ylidene moiety. The results from DFT calculations were in good agreement with the experimental energy barriers.
- Lyapchev, Rumen,Petrov, Petar,Dangalov, Miroslav,Vassilev, Nikolay G.
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p. 194 - 209
(2017/10/09)
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- Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes
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A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.
- Zhang, Song-Lin,Deng, Zhu-Qin
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p. 8966 - 8970
(2016/10/05)
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- Tris(pentafluorophenyl)borane-Catalyzed Acceptorless Dehydrogenation of N-Heterocycles
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Catalytic acceptorless dehydrogenation is an environmentally benign way to desaturate organic compounds. This process is traditionally accomplished with transition-metal-based catalysts. Herein, a borane-catalyzed, metal-free acceptorless dehydrogenation of saturated N-heterocycles is disclosed. Tris(pentafluorophenyl)borane was identified as a versatile catalyst, which afforded several synthetically important N-heteroarenes in up to quantitative yield. Specifically, the present metal-free catalytic system exhibited a uniquely high tolerance toward sulfur functionalities, and demonstrated superior reactivity in the synthesis of benzothiazoles compared to conventional metal-catalyzed systems. This protocol can thus be regarded as the first example of metal-free acceptorless dehydrogenation in synthetic organic chemistry.
- Kojima, Masahiro,Kanai, Motomu
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supporting information
p. 12224 - 12227
(2016/10/13)
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- A Convenient Procedure for the Oxidative Dehydrogenation of N-Heterocycles Catalyzed by FeCl2/DMSO
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A convenient catalytic procedure has been developed for the oxidative dehydrogenations of N-heterocycles. Combining catalytic FeCl2 with DMSO yields a catalyst that promotes the dehydrogenation of tetrahydroquinolines and related heterocycles under 1 bar of O2, affording the corresponding N-heteroaromatic products in moderate yields.
- Zhou, Weiyou,Taboonpong, Piyada,Aboo, Ahmed Hamdoon,Zhang, Lingjuan,Jiang, Jun,Xiao, Jianliang
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supporting information
p. 1806 - 1809
(2016/07/16)
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- Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines
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A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.
- Yi, Xiangli,Xi, Chanjuan
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p. 5836 - 5839
(2015/12/11)
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- Synthesis and Characterization of Iron-Nitrogen-Doped Graphene/Core-Shell Catalysts: Efficient Oxidative Dehydrogenation of N-Heterocycles
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An important goal for nanocatalysis is the development of flexible and efficient methods for preparing active and stable core-shell catalysts. In this respect, we present the synthesis and characterization of iron oxides surrounded by nitrogen-doped-graphene shells immobilized on carbon support (labeled FeOx@NGr-C). Active catalytic materials are obtained in a simple, scalable and two-step method via pyrolysis of iron acetate and phenanthroline and subsequent selective leaching. The optimized FeOx@NGr-C catalyst showed high activity in oxidative dehydrogenations of several N-heterocycles. The utility of this benign methodology is demonstrated by the synthesis of pharmaceutically relevant quinolines. In addition, mechanistic studies prove that the reaction progresses via superoxide radical anions (·O2-).
- Cui, Xinjiang,Li, Yuehui,Bachmann, Stephan,Scalone, Michelangelo,Surkus, Annette-Enrica,Junge, Kathrin,Topf, Christoph,Beller, Matthias
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supporting information
p. 10652 - 10658
(2015/09/28)
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- Pd-catalyzed nucleophilic fluorination of aryl bromides
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On the basis of mechanism-driven reaction design, a Pd-catalyzed nucleophilic fluorination of aryl bromides and iodides has been developed. The method exhibits a broad substrate scope, especially with respect to nitrogen-containing heteroaryl bromides, and proceeds with minimal formation of the corresponding reduction products. A facilitated ligand modification process was shown to be critical to the success of the reaction.
- Lee, Hong Geun,Milner, Phillip J.,Buchwald, Stephen L.
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supporting information
p. 3792 - 3795
(2014/04/03)
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- High throughput one pot synthesis of 2-methylquinolines
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Various 2-methylquinolines have been successfully synthesized by using anilines and ethyl vinyl ether in 1:3 mole ratios in the presence of acetic acid. Stirring at rt for 3-4 h followed by reflux for 3.5-4 h resulted in the corresponding 2-methylquinolines in good yield. Copyright
- Chandrashekarappa, Kiran Kumar H.,Mahadevan, Kittappa M.,Manjappa, Kiran B.
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supporting information
p. 1368 - 1370
(2013/04/23)
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- Design, synthesis and biological evaluation of 2-substituted quinolines as potential antileishmanial agents
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An analogous library of 2-substituted quinoline compounds was synthesized with the aim to identify a potential drug candidate to treat visceral leishmaniasis. These molecules were tested for their in vitro and in vivo biological activity against Leishmania donovani. Metabolic stability of these compounds was also improved through the introduction of halogen substituents. Compound (26g), found to be the most active; exhibited an IC50 value of 0.2 μM and >180 fold selectivity. The hydrochloride salt of (26g) showed 84.26 ± 4.44 percent inhibition at 50 mg/kg × 5 days (twice daily, oral route) dose in L. donovani/hamster model. The efficacy was well correlated with the PK data observed which indicating that the compound is well distributed.
- Gopinath, Vadiraj S.,Pinjari, Jakir,Dere, Ravindra T.,Verma, Aditya,Vishwakarma, Preeti,Shivahare, Rahul,Moger, Manjunath,Kumar Goud, Palusa Sanath,Ramanathan, Vikram,Bose, Prosenjit,Rao,Gupta, Suman,Puri, Sunil K.,Launay, Delphine,Martin, Denis
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p. 527 - 536
(2013/10/22)
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- Facile synthesis of 2-methylquinolines from anilines on mesoporous N-doped TiO2 under UV and visible light
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Nitrogen-doped TiO2 was synthesized by a simple wet method using a nitrogen precursor hydrazine hydrate and nano TiO2. This photocatalyst was characterized by X-ray diffraction, highresolution transmission electron microscopy, diffused reflectance spectra, photoluminescence, and X-ray photoelectron spectroscopy. XPS analysis indicates the incorporation of anionic nitrogen in TiO2 lattice as O-Ti-N linkage. N2 adsorption-desorpion isotherm indicates the mesoporous nature of N-TiO2 with the surface area 130.0 m2/g. Sizes of N-TiO2 particles are found to be in the range of 5-30 nm by HRTEM images. DRS spectra reveal the extended absorption to the visible range. N-TiO2 is found to be more efficient than Ag-TiO2, Au-TiO2, and Pt-TiO2 in quinaldine synthesis under visible light. Copyright Taylor & Francis Group, LLC.
- Selvam,Swaminathan
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p. 500 - 508
(2013/05/21)
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- Acceptorless dehydrogenation of nitrogen heterocycles with a versatile iridium catalyst
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Gas up: A cyclometalated iridium complex is found to catalyze the dehydrogenation of various benzofused N-heterocycles, thus releasing H 2. Driven by as low as 0.1 mol % catalyst, the reaction affords quinolines, indoles, quinoxalines, isoquinolines, and β-carbolines in high yields. Copyright
- Wu, Jianjun,Talwar, Dinesh,Johnston, Steven,Yan, Ming,Xiao, Jianliang
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supporting information
p. 6983 - 6987
(2013/07/26)
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- Synthesis and antifungal activity of diverse C-2 pyridinyl and pyridinylvinyl substituted quinolines
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Diverse 2-pyridinyl quinolines 6-12 and 2-pyridinilvinyl quinolines 13-17 were prepared using a straightforward synthesis based on the BiCl 3-catalyzed multicomponent imino Diels-Alder (imino DA) reaction or a novel tandem imino DA/catalytic tetrahydroquinoline ring oxidation/Perkin condensation sequential process. All members of the series showed activities against dermatophytes and some of them possessed a broad spectrum of action. 2-(Pyridin-4-yl)quinoline 9 and 2-(2-pyridin-4-yl)vinyl)quinoline 16 showed the best MIC80 and MIC50 against the clinically important fungi Candida albicans and non-albicans Candida species. In turn, 6-ethyl-2-(pyridin-2-yl)quinoline 6 showed the best properties against standardized as well as clinical strains of Cryptococcus neoformans.
- Kouznetsov, Vladimir V.,Meléndez Gómez, Carlos M.,Derita, Marcos G.,Svetaz, Laura,Del Olmo, Esther,Zacchino, Susana A.
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p. 6506 - 6512
(2013/01/14)
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- Nano Pt-TiO2 for an efficient one-pot photocatalytic synthesis of quinaldines from anilines and ethanol
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Nanosized platinum particles loaded on the TiO2 nanoparticles were prepared to assess its photocatalytic activity in simple one-pot synthesis of quinaldines from anilines in ethanol using UV light. The catalyst was characterized by X-ray diffra
- Selvam, Kaliyamoorthy,Sreedhar, Bojja,Swaminathan, Meenakshisundaram
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experimental part
p. 761 - 773
(2012/08/07)
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- One-pot photocatalytic synthesis of quinaldines from nitroarenes with Au loaded TiO2 nanoparticles
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One-pot photocatalytic synthesis of quinaldines from nitroarenes using Au-TiO2 nanoparticles is reported. Au-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and the products undergo condensation-cyclization process to give quinaldines.
- Selvam,Swaminathan
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scheme or table
p. 389 - 393
(2011/12/15)
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- Novel redox photocatalyst Pt-TiO2 for the synthesis of 2-Methylquinolines from nitroarenes
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An eco-friendly and efficient procedure for synthesis of 2-methylquinoline derivatives from nitroarenes has been developed by a simple one-pot reaction on the surface of platinum-loaded TiO2 with neat ethanol under UV irradiation without any harsh reagent according to green chemistry. TiO 2 catalysts with various amounts of Pt loadings were prepared by photodeposition using chloroplatinic acid solution and characterized by XRD, BET, AFM, HR-TEM, XPS, and DRS. XRD patterns showed that the crystal structure of Pt-TiO2 still remained as anatase phase. The UV-vis spectra indicated that Pt promoted the absorption of visible light. The XPS measurements reveal that platinum particles are present mainly in metallic form. AFM and HR-TEM analysis revealed the presence of nonspherical shaped platinum nanoparticles of the diameter 312 nm. Pt-TiO2 on irradiation induces a combined redox reaction with nitroarene and alcohol and this is followed by condensationcyclization of aniline and oxidation products to give 2-methylquinolines
- Selvam, Kaliyamoorthy,Swaminathan, Meenakshisundaram
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experimental part
p. 953 - 959
(2011/10/18)
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- Assembly of substituted 2-alkylquinolines by a sequential palladium-catalyzed Ci-N and Ci-C bond formation
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Diversity: A range of substituted 2-alkylquinolines can be prepared in a general and efficient synthetic approach that employs mild reaction conditions (see scheme). The synthesis is based on a sequential palladium-catalyzed Ci-N and Ci-C bond formation, followed by palladium-catalyzed aromatization, and results in the formation of the desired compounds in one step. Copyright
- Matsubara, Yoshio,Hirakawa, Saori,Yamaguchi, Yoshihiro,Yoshida, Zen-Ichi
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experimental part
p. 7670 - 7673
(2011/10/05)
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- Iron/acetic acid-mediated carbon degradation: A facile route for the synthesis of quinoline derivatives
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A new carbon degradation protocol which results in the formation of quinoline derivatives is described. The reactions involved the use of mild reaction conditions and an inexpensive reducing reagent (Fe/AcOH).
- Ramesh, Chintakunta,Kavala, Veerababurao,Kuo, Chun-Wei,Yao, Ching-Fa
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supporting information; experimental part
p. 5234 - 5237
(2010/11/03)
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- Au-doped TiO2 nanoparticles for selective photocatalytic synthesis of quinaldines from anilines in ethanol
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A convenient eco-friendly photocatalytic synthesis of quinaldines has been developed by a simple one-pot reaction of anilines in ethanol solution with Au-loaded TiO2 under UV irradiation. Upon irradiation in the presence of Au-TiO2, aniline and oxidation products derived from ethanol undergo condensation-cyclization to afford quinaldines.
- Selvam,Swaminathan
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scheme or table
p. 4911 - 4914
(2010/10/02)
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- One-pot synthesis of substituted quinolines by iridium-catalyzed three-component coupling reaction
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A convenient and efficient synthesis of substituted quinolines in a simple one-pot reaction of an arylamine 1, an aromatic aldehyde or aliphatic aldehyde 2 and an aliphatic aldehyde 3 in the presence of transition metal complexes or Lewis acids was developed. Among them, the iridium catalyst [Ir(cod)Cl] 2 catalyzed the reaction most efficiently. Copyright
- Igarashi, Takeyuki,Inada, Takashi,Sekioka, Tadao,Nakajima, Takayuki,Shimizu, Isao
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p. 106 - 107
(2007/10/03)
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- N8, n13 -disubstituted quino[4,3,2-kl]acridinium salts as therapeutic agents
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The present invention pertains to certain N8,N13-disubstituted quino[4,3,2-kl]acridinium salts of formula (Q?) which inhibit telomerase wherein: p is an integer from 0 to 4; q is an integer from 0 to 3; r is an integer from 0 to 4; each RA is —H or a ring substituent; each RB is —H or a ring substituent; each RC is —H or a ring substituent; RN8 is a nitrogen substituent; RN13 is a nitrogen substituent; and, Q is an anion. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit telomerase, to regulate cell proliferation, and in the treatment of proliferative conditions, such as cancer.
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