- COMPOUNDS AND METHODS FOR TREATING CANCER
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Compounds useful as modulators of AhR, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate AhR-mediated disorders such as cancers and inflammatory diseases are provided.
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Paragraph 0200
(2020/11/30)
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- Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts
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The enantioselective syntheses of axially chiral heterobiaryls were accomplished through the aromatic electrophilic halogenation of 3-(quinolin-8-yl)phenols with bifunctional organocatalysts that control the molecular conformations during successive halogenations. Axially chiral quinoline derivatives, which have rarely been synthesized in an enantioselective catalytic manner, were afforded in moderate-to-good enantioselectivities through bromination, and an analogous protocol also enabled enantioselective iodination. In addition, this catalytic reaction, which allows enantioselective control through the use of mono-ortho-substituted substrates, allowed the asymmetric synthesis of 8-arylquinoline derivatives bearing two different halogen groups in high enantioselectivities.
- Miyaji, Ryota,Asano, Keisuke,Matsubara, Seijiro
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supporting information
p. 9996 - 10000
(2017/08/01)
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- Axially Chiral Bifunctional 8,8′-Biquinolyl: Synthesis of 7,7′-Dihydroxymethyl-8,8′-biquinolyl via Pd-Catalyzed Double C-H Oxidation of 7,7′-Dimethyl-8,8′-biquinolyl
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Bifunctional C2-symmetric 7,7′-dihydroxymethyl-8,8′-biquinolyl (2) was synthesized in short steps via (i) Cu/Pd-catalyzed homo coupling of 7-methyl-8-bromoquinoline and (ii) Pd(II)-catalyzed double C-H oxidation. Axial chirality of 2 and its synthetic precursor 7,7′-dimethyl-8,8′-biquinolyl (3) is stable. Optically active 2 was obtained through separation of racemic 2 by chiral column HPLC or Pd(II)-catalyzed double C-H oxidation of optically active 3. The absolute stereochemistry of enantiomers of 2 and 3 was determined using the exciton chirality method.
- Kitamura, Mitsuru,Fukuma, Hiroaki,Kobayashi, Mitsuaki,Okayama, Shinya,Okauchi, Tatsuo
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p. 3956 - 3960
(2016/05/24)
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- Kinetic Resolution of Axially Chiral 5- or 8-Substituted Quinolines via Asymmetric Transfer Hydrogenation
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An efficient kinetic resolution of axially chiral 5- or 8-substituted quinoline derivatives was developed through asymmetric transfer hydrogenation of heteroaromatic moiety, simultaneously obtaining two kinds of axially chiral skeletons with up to 209 of selectivity factor. This represents the first successful application of asymmetric transfer hydrogenation of heteroaromatics in kinetic resolution of axially chiral biaryls.
- Wang, Jie,Chen, Mu-Wang,Ji, Yue,Hu, Shu-Bo,Zhou, Yong-Gui
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supporting information
p. 10413 - 10416
(2016/09/04)
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- BROMINATION OF QUINOLINE DERIVATIVES WITH N-BROMOSUCCINIMIDE. ISOMERIC COMPOSITION OF THE BROMINATION PRODUCTS BY PMR AND GLC
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The bromination of quinoline and substituted quinolines with N-bromosuccinimide in concentrated H2SO4 takes place exclusively in the homocyclic part.Bromo-substituted quinolines can be obtained by this method.The bromination products were identified by PMR spectroscopy.The differences among the mono-, di-, and trisubstituted (in the benzene ring) compounds were established on the basis of the type of spectrum of the protons of the homocyclic part of the molecule.The compositions of the reaction mixtures were studied by GLC.
- Tochilkin, A. I.,Kovel'man, I. R.,Prokof'ev, E. P.,Gracheva, I. N.,Levinskii, M. V.
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p. 892 - 897
(2007/10/02)
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