- Synthesis of new chiral 2-functionalized-1,2,3,4-tetrahydroquinoline derivatives via asymmetric hydrogenation of substituted quinolines
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The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee.
- Maj, Anna M.,Suisse, Isabelle,Hardouin, Christophe,Agbossou-Niedercorn, Francine
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- Highly enantioselective hydrogenation of new 2-functionalized quinoline derivatives
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The asymmetric hydrogenation of a new series of 2-functionalized quinolines has been developed in the presence of in situ generated catalysts obtained from [Ir(cod)Cl]2/(R)-bisphosphine/I2 combinations. The enantioselectivity levels
- Maj, Anna M.,Suisse, Isabelle,Méliet, Catherine,Hardouin, Christophe,Agbossou-Niedercorn, Francine
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- A new, convenient, highly selective free-radical hydroxymethylation of heteroaromatic bases by persulfate oxidation of ethylene glycol and glycerol, catalysed by AgNO3
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A new, convenient and selective source of hydroxymethyl ( .CH2OH) radical has been developed by persulfate oxidation of ethylene glycol with AgNO3 catalysis. The .CH 2OH radical is selectively trapped
- Minisci, Francesco,Porta, Ombretta,Recupero, Francesco,Punta, Carlo,Gambarotti, Cristian,Pruna, Barbara,Pierini, Monica,Fontana, Francesca
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- Unprecedented Reaction Pathway of Sterically Crowded Calcium Complexes: Sequential C?N Bond Cleavage Reactions Induced by C?H Bond Activations
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Five bis(quinolylmethyl)-(1H-indolylmethyl)amine (BQIA) compounds, that is, {(quinol-8-yl-CH2)2NCH2(3-Br-1H-indol-2-yl)} (L1H) and {[(8-R3-quinol-2-yl)CH2]2NCH(R2)[3-R1-1H-indol-2-yl]} (L2–5H) (L2H: R1=Br, R2=H, R3=H; L3H: R1=Br, R2=H, R3=iPr; L4H: R1=H, R2=CH3, R3=iPr; L5H: R1=H, R2=nBu, R3=iPr) were synthesized and used to prepare calcium complexes. The reactions of L1–5H with silylamido calcium precursors (Ca[N(SiMe2R)2]2(THF)2, R=Me or H) at room temperature gave heteroleptic products (L1, 2)CaN(SiMe3)2 (1, 2), (L3, 4)CaN(SiHMe2)2 (3 a, 4 a) and homoleptic complexes (L3, 5)2Ca (D3, D5). NMR and X-ray analyses proved that these calcium complexes were stabilized through Ca???C?Si, Ca???H?Si or Ca???H?C agostic interactions. Unexpectedly, calcium complexes ((L3–5)CaN(SiMe3)2) bearing more sterically encumbered ligands of the same type were extremely unstable and underwent C?N bond cleavage processes as a consequence of intramolecular C?H bond activation, leading to the exclusive formation of (E)-1,2-bis(8-isopropylquinol-2-yl)ethane.
- Yang, Yang,Wang, Haobing,Ma, Haiyan
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- STIMULI - OR BIO- RESPONSIVE COPOLYMERS, THE POLYMERSOMES COMPRISING THE SAME AND THEIR USE IN DRUG DELIVERY
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The present invention concerns amphiphilic copolymers that may be photo- or redox-cleavable and that may assemble into polymersomes. It also concerns their process of preparation and their use as drug carriers.
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- Hydroxymethylation of quinolinesviairon promoted oxidative C-H functionalization: synthesis of arsindoline-A and its derivatives
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Herein, we report a mild and efficient hydroxymethylation of quinolinesviaan iron promoted cross-dehydrogenative coupling reaction under external acid free conditions. Various hydroxyalkyl substituted quinolines were achieved in excellent yields with well tolerated functional groups. Importantly, a few of the hydroxylmethylated quinolines were further transformed into respective aldehydes, and were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.
- Shantharjun, Bangarigalla,Vani, Damera,Unnava, Ramanjaneyulu,Sandeep, Mummadi,Reddy, Kallu Rajender
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p. 645 - 652
(2021/02/06)
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- Structural Basis for Developing Multitarget Compounds Acting on Cysteinyl Leukotriene Receptor 1 and G-Protein-Coupled Bile Acid Receptor 1
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G-protein-coupled receptors (GPCRs) are the molecular target of 40% of marketed drugs and the most investigated structures to develop novel therapeutics. Different members of the GPCRs superfamily can modulate the same cellular process acting on diverse pathways, thus representing an attractive opportunity to achieve multitarget drugs with synergic pharmacological effects. Here, we present a series of compounds with dual activity toward cysteinyl leukotriene receptor 1 (CysLT1R) and G-protein-coupled bile acid receptor 1 (GPBAR1). They are derivatives of REV5901-the first reported dual compound-with therapeutic potential in the treatment of colitis and other inflammatory processes. We report the binding mode of the most active compounds in the two GPCRs, revealing unprecedented structural basis for future drug design studies, including the presence of a polar group opportunely spaced from an aromatic ring in the ligand to interact with Arg792.60 of CysLT1R and achieve dual activity.
- Fiorillo, Bianca,Sepe, Valentina,Conflitti, Paolo,Roselli, Rosalinda,Biagioli, Michele,Marchianò, Silvia,De Luca, Pasquale,Baronissi, Giuliana,Rapacciuolo, Pasquale,Cassiano, Chiara,Catalanotti, Bruno,Zampella, Angela,Limongelli, Vittorio,Fiorucci, Stefano
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p. 16512 - 16529
(2021/11/24)
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- Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots
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We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.
- Xi, Zi-Wei,Yang, Lei,Wang, Dan-Yan,Feng, Chuan-Wei,Qin, Yufeng,Shen, Yong-Miao,Pu, Chaodan,Peng, Xiaogang
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p. 2474 - 2488
(2021/02/05)
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- Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols
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We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.
- Aleku, Godwin A.,Leys, David,Roberts, George W.
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p. 3927 - 3939
(2020/07/09)
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- Multikilogram Synthesis of a Potent Dual Bcl-2/Bcl-xL Antagonist. 1. Manufacture of the Acid Moiety and Development of Some Key Reactions
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Our efforts toward the process development of drug candidate 1 are described in a series of two papers. This manuscript focuses on the synthesis of kilogram quantities of acid precursor 2 to provide batches of material for preclinical studies and first-in
- Hardouin, Christophe,Baillard, Sandrine,Barière, Fran?ois,Copin, Chloé,Craquelin, Anthony,Janvier, Solenn,Lemaitre, Sylvain,Le Roux, Stéphane,Russo, Olivier,Samson, Sébastien
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p. 652 - 669
(2019/12/24)
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- Consecutive Intermolecular Reductive Amination/Asymmetric Hydrogenation: Facile Access to Sterically Tunable Chiral Vicinal Diamines and N-Heterocyclic Carbenes
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A highly enantioselective iridium- or ruthenium-catalyzed intermolecular reductive amination/asymmetric hydrogenation relay with 2-quinoline aldehydes and aromatic amines has been developed. A broad range of sterically tunable chiral N,N′-diaryl vicinal diamines were obtained in high yields (up to 95 %) with excellent enantioselectivity (up to >99 % ee). The resulting chiral diamines could be readily transformed into sterically hindered chiral N-heterocyclic carbene (NHC) precursors, which are otherwise difficult to access. The usefulness of this synthetic approach was further demonstrated by the successful application of one of the chiral vicinal diamines and chiral NHC ligands in a transition-metal-catalyzed asymmetric Suzuki–Miyaura cross-coupling reaction and asymmetric ring-opening cross-metathesis, respectively.
- Chen, Ya,Pan, Yixiao,He, Yan-Mei,Fan, Qing-Hua
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p. 16831 - 16834
(2019/11/13)
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- Homogeneous Hydrogenation with a Cobalt/Tetraphosphine Catalyst: A Superior Hydride Donor for Polar Double Bonds and N-Heteroarenes
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The development of catalysts based on earth abundant metals in place of noble metals is becoming a central topic of catalysis. We herein report a cobalt/tetraphosphine complex-catalyzed homogeneous hydrogenation of polar unsaturated compounds using an air- and moisture-stable and scalable precatalyst. By activation with potassium hydroxide, this cobalt system shows both high efficiency (up to 24 000 TON and 12 000 h-1 TOF) and excellent chemoselectivities with various aldehydes, ketones, imines, and even N-heteroarenes. The preference for 1,2-reduction over 1,4-reduction makes this method an efficient way to prepare allylic alcohols and amines. Meanwhile, efficient hydrogenation of the challenging N-heteroarenes is also furnished with excellent functional group tolerance. Mechanistic studies and control experiments demonstrated that a CoIH complex functions as a strong hydride donor in the catalytic cycle. Each cobalt intermediate on the catalytic cycle was characterized, and a plausible outer-sphere mechanism was proposed. Noteworthy, external inorganic base plays multiple roles in this reaction and functions in almost every step of the catalytic cycle.
- Duan, Ya-Nan,Du, Xiaoyong,Cui, Zhikai,Zeng, Yiqun,Liu, Yufeng,Yang, Tilong,Wen, Jialin,Zhang, Xumu
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supporting information
p. 20424 - 20433
(2019/12/27)
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- Method of making and administering quinoline derivatives as anti-cancer agents
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The present invention relates methods of preparing quinoline derivative compounds, and administering such compounds in the treatment of solid and non-solid tumors, notably on liver cancer.
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Page/Page column 14
(2016/05/24)
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- Design, synthesis and preliminary bioactivity evaluations of substituted quinoline hydroxamic acid derivatives as novel histone deacetylase (HDAC) inhibitors
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Inhibition of HDACs activity has become a promising therapeutic strategy in clinical practice to reverse the abnormal epigenetic states of cancer and other diseases. Therefore, HDAC inhibitors become a relatively new class of anti-cancer agent. In the present study, we reported the design and synthesis of a series of novel HDAC inhibitors using various substituted quinoline rings as the cap group. In vitro studies showed that some compounds have good inhibitory activities against HDACs and potent antiproliferative activities in some tumor cell lines. Especially, compound 9w (IC50 = 85 nM), exhibited better inhibitory effect compared with SAHA (IC50 = 161 nM).
- Wang, Lei,Hou, Xuben,Fu, Huansheng,Pan, Xiaole,Xu, Wenfang,Tang, Weiping,Fang, Hao
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p. 4364 - 4374
(2015/08/03)
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- Dual [Fe+Phosphine] catalysis: Application in catalytic wittig olefination
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Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity was used within the context of catalytic Wittig olefination. Picture perfect: Iron hydride complexes of the general formula P2Fe(NO)CO)H are highly active catalysts for the hydrosilylation of aldehydes or ketones and phosphine oxides. Depending on the solvent, the in situ reduction of the phosphine oxide can be faster than the corresponding hydrosilylation of a carbonyl group. This unusual activity is used within the context of catalytic Wittig olefination. EWG=Electron-withdrawing group.
- Rommel, Susanne,Belger, Christian,Begouin, Jeanne-Marie,Plietker, Bernd
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p. 1292 - 1301
(2015/04/27)
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- Efficient synthesis of cis-2,6-di-(2-quinolylpiperidine)
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An efficient synthesis of cis-2,6-di-(2-quinolylpiperidine) has been developed. The key steps involve Wittig reaction of N-Cbz-protected cis-piperidine-2,6-dicarboxaldehyde (3) with 2-(triphenylphosphinyl-methyl) quinoline bromide (4) and sequential removal of the N-Cbz group and double bond reduction. This synthetic procedure provides an efficient preparation for this useful norlobelane analogue.
- Ding, Derong,Dwoskin, Linda P.,Crooks, Peter A.
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p. 5211 - 5213
(2013/09/02)
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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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- NEW PYRAZOLE DERIVATIVES HAVING CRTH2 ANTAGONISTIC BEHAVIOUR
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The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.
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Page/Page column 42
(2012/06/15)
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- New pyrazole derivatives having CRTh2 antagonistic behaviour
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The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.
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Page/Page column 25
(2012/06/05)
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- Chiral amine-imine ligands based on trans-2,5-disubstituted pyrrolidines and their application in the palladium-catalyzed allylic alkylation
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A series of amine-imine bidentate ligands based on a trans-2,5-disubstituted pyrrolidine and pyridine moieties have been prepared. The use of these ligands in the palladium-catalyzed allylic alkylation reaction of rac-(E)-1,3-diphenylprop-2-enyl acetate is reported. The results suggest that these ligands are good catalyst precursors for the reaction. Electronic modification on the pyridine ring of the ligands does not have a significant effect on the enantioselectivity of the reaction but does on the reaction rate, while structural modification on either the pyridine or the pyrrolidine moiety affords dramatic changes on the outcome of the stereochemistry. Evidence from various studies suggested that during the palladium-catalyzed allylic alkylation reaction, nucleophilic attack onto the 1,3-diphenylallyl moiety in the transition state occurs mainly trans to the pyridine ring of the less stable conformation of the palladium complexes.
- Chen, Hongfeng,Sweet, James A.,Lam, Kin-Chung,Rheingold, Arnold L.,McGrath, Dominic V.
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experimental part
p. 1672 - 1682
(2009/12/04)
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- (N-Arylaminomethyl)pyridine-N-oxides: Synthesis and characterization of potential ligand systems and the formation of their N,O-chelate aluminum complexes
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Pyridine-N-oxide-2-carbaldehyde (4a) was converted to the corresponding imine (5a) by treatment with 2,6-diisopropylaniline. Subsequent reduction with a sodium borohydride gave the corresponding (N-arylaminomethyl)pyridine-N-oxide derivative (6a). A series of analogous compounds was prepared starting from the respective (aldimino)quinoline-N-oxide (4b) or (ketimino)pyridine-N-oxide (10) systems. Deprotonation of the (aminomethyl)pyridine-N-oxides resulted in a series of unexpected reactions, such as coupling, internal redox reactions or fragmentation. Eventually, the N,O-chelate aluminum complexes (22, 23) derived from the (aminoethyl)pyridine-N-oxide ligand systems could be obtained by treatment of the respective iminopyridine-N-oxides with trimethylaluminum. Many products were characterized by X-ray diffraction.
- Nienkemper, Katrin,Kehr, Gerald,Kehr, Seda,Fr?hlich, Roland,Erker, Gerhard
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p. 3063 - 3073
(2008/12/22)
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- Hydroxymethylations of aryl halides by Pd-catalyzed cross-couplings with (benzoyloxy)methylzinc iodide - Scope and limitations of the reaction
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Palladium-catalyzed cross-coupling reactions of (benzoyloxymethyl)zinc iodide with diverse (het)aryl halides leading to (benzoyloxymethyl)(het)arenes were studied to define the scope of this reaction. It has been found that this reaction is only applicable for electron-deficient aryl halides and the most efficient it is for 2-halopyridines and 4-halopyrimidines. Deprotection of the intermediates gives (hydroxymethyl)pyridines and -pyrimidines in high yields. Georg Thieme Verlag Stuttgart.
- Hasník, Zbyněk,?ilhár, Peter,Hocek, Michal
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p. 543 - 546
(2008/12/22)
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- 4'-O-SUBSTITUTED ISOINDOLINE DERIVATIVES AND COMPOSITIONS COMPOSITIONS COMPRISING AND METHODS OF USING THE SAME
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Provided are 4'-O substituted isoindoline compounds, and pharmaceutically acceptable salts, solvates, clathrates, stereoisomers, and prodrugs thereof. Methods of use, and pharmaceutical compositions of these compounds are disclosed.
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Page/Page column 66-67
(2008/12/07)
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- Samarium-promoted coupling of pyridine-based heteroaryl analogues of benzylic acetates with carbonyl compounds
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(Chemical Equation Presented) 2-Substituted pyridine, quinoline, isoquinoline, bipyridine, and 1,10-phenanthroline analogues of benzylic acetates undergo Sml2-promoted coupling with aldehydes and ketones to afford (2-hydroxyalkyl)heteroaromatics.
- Weitgenant, Jeremy A.,Mortison, Jonathan D.,Helquist, Paul
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p. 3609 - 3612
(2007/10/03)
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- Analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them
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A compound of the formula wherein the substituents are defined as in the specification which compounds are useful in the treatment of cancer.
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- 5-MEMBERED N-HETEROCYCLIC COMPOUNDS WITH HYPOGLYCEMIC AND HYPOLIPIDEMIC ACTIVITY
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Use of a compound of the formula: wherein R represents a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; X represents a bond, an oxygen atom, a sulfur atom, or a group of the formula: -CO-, -CS-, -CR(OR)- or -NR- wherein each of R and R represents a hydrogen atom or a hydrocarbon group which may be substituted, R represents a hydrogen atom or a protective group for a hydroxyl group; m represents an integer of 0 to 3; Y represents an oxygen atom, a sulfur atom, or a group of the formula: -SO-, -SO2-, -NR-, -CONR- or -NRCO- wherein R represents a hydrogen atom or a hydrocarbon group which may be substituted; ring A represents an aromatic ring which may further have 1 to 3 substituents; n represents an integer of 1 to 8; ring B represents a nitrogen-containing 5-membered hetero ring which may further be substituted by an alkyl group; X represents a bond, an oxygen atom, a sulfur atom, or a group of the formula: -SO-, -SO2-, -O-SO2- or -NR- wherein R represents a hydrogen atom or a hydrocarbon group which may be substituted; R represents a hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted; W represents a bond or a divalent hydrocarbon residue having 1 to 20 carbon atoms; R represents a group of the formula: -OR (R represents a hydrogen atom or a hydrocarbon group which may be substituted) or -NRR (each of R and R, whether identical or not, represents a hydrogen atom, a hydrocarbon group which may be substituted, a heterocyclic group which may be substituted, or an acyl group which may be substituted; R and R may bind together to form a ring); or a salt thereof, for the manufacture of a pharmaceutical preparation for preventing or treating syndrome X.
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- New analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them
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A compound of the formula wherein the substituents are defined as in the specification which compounds are useful in the treatment of cancer.
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- Conformational control of propeller-like chirality in Zn(II) complexes: Tightly balanced steric bias
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The conformational behavior of a series of chiral tripodal ligand-Zn(II) complexes was examined. The ligands adopt propeller-like conformations upon complexation of trigonal bipyramidal metal ions such as Zn(II), with the chirality of the propeller determ
- Chiu, Yu-Hung,Dos Santos, Osvaldo,Canary, James W.
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p. 12069 - 12078
(2007/10/03)
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- Oxidation of substituted pyridines PyrCHRSiMe3 (R=H, Me, Ph) and substituted quinolines QnCH2SiMe3 with hypervalent iodine reagents
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Oxidation of a variety of substituted pyridines, PyrCHRSiMe3 (R = H, Me, Ph) and quinolines, QnCH2SiMe3 with hypervalent iodine reagents PIDA, (PhI(OCOCH3)2) and PIFA, (PhI(OCOCF3)2) has been studied. Oxy-desilylation with PIDA/TBAF gives low to moderate yields of PyrCHROR1 and QnCH2OR1 (R1 = H, Ac), while good yields of PyrCHROH and QnCH2OH are obtained when PIFA is used.
- Andrews, Ian P.,Lewis, Norman J.,McKillop, Alexander,Wells, Andrew S.
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p. 1151 - 1158
(2007/10/03)
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- The Dehydrogenation of Tertiary Amines with Heteroaromatic N-Oxide Neighbour Group
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The mercury EDTA dehydrogenation of 2-aminomethylpyridine- resp. -quinoline-N-oxides is examined with the aspect of a possible neighbourgroup effect of the amine oxide function.
- Moehrle, H.,Troester, G.
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p. 344 - 349
(2007/10/02)
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- ELECTRONIC NATURE OF THE AZA SUBSTITUENT OF PYRIDYL AND QUINOLYL GROUPS FOR REACTIVITIES IN AN INSULATED SYSTEM
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A new set of ?0 values was determined for all positions of pyridyl and quinolyl groups, reliably excluding steric effect by perihydrogen, on the basis of the rates of the alkaline hydrolysis of substituted 2-methylbenzoates and pyridylmethyl and quinolylmethyl 2-methyl-benzoates in 70percent aq acetone.
- Sawada, Masami,Ichihara, Masaharu,Ando, Takashi,Yukawa, Yasuhide,Tsuno, Yuho
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p. 4917 - 4920
(2007/10/02)
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