- Synthesis of Indole-Dihydroisoquinoline Sulfonyl Ureas via Three-Component Reactions
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Isoquinolines activated with sulfamoyl chlorides were reacted with indoles in a 3-component reaction to generate a library of dihydroisoquinoline derivatives. Using a differential protecting group strategy, products could be further derivatised. Synthesis of isoquinoline starting materials using several different methods is also described.
- Pearson, Stuart E.,Fillery, Shaun M.,Goldberg, Kristin,Demeritt, Julie E.,Eden, Jonathan,Finlayson, Jonathan,Patel, Anil
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p. 4963 - 4981
(2018/12/13)
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- Inhibitors of the detoxifying enzyme of the phytoalexin brassinin based on quinoline and isoquinoline scaffolds
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The detoxification of the phytoalexin brassinin to indole-3-carboxaldehyde and S-methyl dithiocarbamate is catalyzed by brassinin oxidase (BOLm), an inducible fungal enzyme produced by the plant pathogen Leptosphaeria maculans. Twenty-six substituted quinolines and isoquinolines are synthesized and evaluated for antifungal activity against L. maculans and inhibition of BOLm. Eleven compounds that inhibit BOLm activity are reported, of which 3-ethyl-6-phenylquinoline displays the highest inhibitory effect. In general, substituted 3-phenylquinolines show significantly higher inhibitory activities than the corresponding 2-phenylquinolines. Overall, these results indicate that the quinoline scaffold is a good lead to design paldoxins (phytoalexin detoxification inhibitors) that inhibit the detoxification of brassinin by L. maculans.
- Pedras, M. Soledade C.,Abdoli, Abbas,Sarma-Mamillapalle, Vijay K.
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- Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air
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Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. (Figure presented.).
- Zhang, Jingyu,Chen, Shiya,Chen, Fangfang,Xu, Wensheng,Deng, Guo-Jun,Gong, Hang
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supporting information
p. 2358 - 2363
(2017/07/22)
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- CARBONITRILE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATORS
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The present invention relates to a compound of Formula 1, 2 or 3: I II III wherein A is N or -CR0--, where R0 is hydrogen, C1-C6 linear or branched chain alkyl, etc., Z is -CRe --, or, -N--, where Re is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R1 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R2 are independently hydrogen or C1-C6 linear or branched chain alkyl; R3 and R4 are independently hydrogen, C1C6 linear or branched chain alkyl, etc.;. R5 and R6 are independently hydrogen or C1-C6 linear or branched chain alkyl, etc.; R8 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R9 and R10 are independently hydrogen or C1- C6 linear or branched chain alkyl, etc.; Q is --CO--, --(CH2)q--, --(CHRs)q--, or -(CRsRt)q- -, where Rs and Rt are independently C1-C6 linear or branched chain alkyl, aryl, alkylaryl, heteroaryl or alkylheteroaryl; where q is 0, 1, 2, or 3; and, where n is 0, 1, 2, 3, 4 or 5; or, a pharmaceutically acceptable salt thereof, for the treatment of certain diseases, particularly those affected or mediated by the androgen receptor; to compbinations comprising such compounds with a second pharmaceutically active ingredient; to compositions containing such combinations; and to such combinations for the treatment of various diseases, particularly, those affected or mediated by the androgen receptor.
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Page/Page column 132-133
(2015/12/17)
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- Luminescent Pt(ii) complexes bearing dual isoquinolinyl pyrazolates: Fundamentals and applications
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A series of four Pt(ii) metal complexes with trans-arranged isoquinolinyl azolates have been prepared, [Pt(Lx)2], x = 1-4, (1-4). The associated chelates possess various substituents; namely: one t-butyl (But) at the 6-position (L1), two But groups at the 5,7-positions (L2), one dip (2,6-di-isopropylphenyl) group at the 6-position (L3), and a single dip group at the 4-position of the 1-isoquinolinyl fragment (L4), respectively. Crystal structures of 1 and 4 were determined to shed light on the relationship of photophysics and packing arrangements. Their photophysical properties were measured and compared, for which the solid-state emission spectra of 2 and 4 are nearly identical to the solution spectra of all the Pt(ii) complexes, showing the formation of isolated molecular entities. In contrast, the Pt(ii) complexes 1 and 3 are found to be sensitive to their morphological states and external stimulus. This is confirmed by the gradual red-shifting of the emission with increasing concentration in the PMMA matrix, and the eventual formation of the broadened, metal-metal-to-ligand charge transfer (MMLCT) emission, by (i) wetting with acetone and drying in air, or (ii) grinding with a mortar and pestle, respectively. Organic light-emitting diodes (OLEDs) were also fabricated using multiple layered architecture and lowered doping concentration (e.g. 8 wt%), the latter is for avoiding dopant aggregation in the emitting layer. The associated OLED performances (i.e. ηmax = 11.5%, 8.5%, and 11.2% for 1, 2 and 3) confirmed their suitability and potential as dopants for phosphorescent OLEDs.
- Ku, Hsiao-Yun,Tong, Bihai,Chi, Yun,Kao, Hao-Che,Yeh, Chia-Chi,Chang, Chih-Hao,Lee, Gene-Hsiang
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supporting information
p. 8552 - 8563
(2015/05/20)
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- ARYL CARBOXAMIDE DERIVATIVES AS SODIUM CHANNEL INHIBITORS FOR TREATMENT OF PAIN
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The present invention provides compounds that are inhibitors of voltage-gated sodium channels (Nav), in particular Nav 1.7, and are therefore useful for the treatment of diseases treatable by inhibition of these channels, in particular, chronic pain disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.
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Page/Page column 76
(2011/09/19)
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- New substituted isoquinoline and isoquinolinone derivatives
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The invention relates to 6-substituted isoquinoline and isochinolone derivatives of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.
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Page/Page column 15
(2010/04/23)
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- Synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8] phenanthrolin-(5H)-6-ones through a Pd-mediated Suzuki-Miyaura heteroaryl-aryl coupling reaction
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In the course of the search for non-camptothecin topoisomerase I inhibitors we have undertaken the synthesis of N-substituted benzo[c][1,7]- and benzo[c][1,8]phenanthrolinone derivatives. An intermolecular Suzuki-Miyaura heteroaryl-aryl coupling reaction was planned as the key step. Then a nitro reduction followed by a concomitant lactamization achieved the construction of the tetracycle structures. This methodology permitted a rapid and efficient elaboration of biologically potent compounds.
- Genès, Constance,Michel, Sylvie,Tillequin, Fran?ois,Porée, Fran?ois-Hugues
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experimental part
p. 10009 - 10015
(2010/02/27)
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- SUBSTITUTED ISOQUINOLINE AND ISOQUINOLINONE DERIVATIVES
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The invention relates to 6-substituted isoquinoline and isochinolone derivatives of the formula (I) useful for the treatment and/or prevention of diseases associated with Rho-kinase and/or Rho-kinase mediated phosphorylation of myosin light chain phosphatase, and compositions containing such compounds.
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Page/Page column 53
(2008/12/06)
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- CYCLOALKYLAMINE SUBSTITUTED ISOQUINOLONE AND ISOQUINOLINONE DERIVATIVES
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The invention relates to 6-substituted isoquinoline and isoquinolinone derivatives of the formula 1 useful for the treatment and prevention of diseases associated with Rho-kinase and Rho- kinase mediated phosphorylation of myosin light chain phosphatase, and composition containing such compound
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Page/Page column 42
(2008/12/06)
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- NOVEL ANTIMALARIA AGENT CONTAINING HETEROCYCLIC COMPOUND
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Disclosed is an antimalarial agent containing a compound represented by the formula: [wherein A1 represents a 3-pyridyl group that may have a substituent, a 6-quinolyl group that may have a substituent, or the like; X1 represents a group represented by the formula -C(=O)-NH- or the like; E represents a furyl group, a thienyl group or a phenyl group; with the proviso that A1 may have one to three substituents, and E has one of two substituents] or a salt thereof or hydrates thereof.
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Page/Page column 58
(2008/06/13)
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- NOVEL ANTIFUNGAL AGENT COMPRISING HETEROCYCLIC COMPOUND
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The present invention provides an antifungal agent represented by the formula: [wherein A1 represents a 3-pyridyl group which may have a substituent, a quinolyl group which may have a substituent, or the like; X1 represents a group represented by the formula -NH-C(=O)-, a group represented by the formula -C(=O)-NH-, or the like; E represents a furyl group, a thienyl group, a pyrrolyl group, a phenyl group, a pyridyl group, a tetrazolyl group, a thiazolyl group or a pyrazolyl group; with the proviso that A1 may have 1 to 3 substituents, and E has one or two substituents].
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Page/Page column 66
(2010/11/08)
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- NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT
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The present invention relates to niacin receptor agonists of formula: (I); as well as pharmaceutically acceptable salts and solvates. The compounds are useful for treating dyslipidemias, and in particular, reducing serum LDL, VLDL and triglycerides, and raising HDL levels. Pharmaceutical compositions and methods of treatment are also included.
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Page/Page column 31; 66-67
(2010/11/30)
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- Substituted phenylalkanoic acid derivatives and use thereof
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A compound represented by the formula (I) or a salt thereof: wherein n represents an integer of 1 to 3, R represents an alkyl group having 3 to 8 carbon atoms, a group represented by the following formula: R1(CH2)k— (wherein k represents 0 or an integer of 1 to 3; R1 represents a saturated cyclic alkyl group having 3 to 7 carbon atoms or a saturated condensed cyclic alkyl group having 6 to 8 carbon atoms, and the group R1 may be substituted with a lower alkyl group having 1 to 4 carbon atoms) and the like, and Ar represents a condensed bicyclic group such as naphthalen-1-yl group, which has suppressing action on prostaglandin and leukotriene production and is useful for prophylactic and/or therapeutic treatment of various inflammatory diseases and the like caused by these lipid mediators.
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- FUNGAL CELL WALL SYNTHESIS GENE
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A reporter system reflecting the transport process that transports GPI-anchored proteins to the cell wall was constructed and compounds inhibiting this process were discovered. Further, genes conferring resistance to the above compounds were identified and methods of screening for compounds that inhibit the activity of the proteins encoded by these genes were developed.Therefore, through the novel compounds, the present invention showed that antifungal agents having a novel mechanism, i.e. inhibiting the process that transports GPI-anchored proteins to the cell wall, could be achieved.
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- 2-Arylindoles as gonadotropin releasing hormone (GnRH) antagonists: Optimization of the tryptamine side chain
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A series of 2-arylindoles containing novel heteroaromatic substituents on the tryptamine tether, based on compound 1, was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. Successful modifications of 1 included chain length variation (reduction) and replacement of the pyridine with heteroaromatic groups. These alterations culminated in the discovery of compound 27kk which had excellent in vitro potency and oral efficacy in rodents.
- Young, Jonathan R.,Huang, Song X.,Walsh, Thomas F.,Wyvratt Jr., Matthew J.,Yang, Yi Tien,Yudkovitz, Joel B.,Cui, Jisong,Mount, George R.,Ren, Rena Ning,Wu, Tsuei-Ju,Shen, Xiaolan,Lyons, Kathryn A.,Mao, An-Hua,Carlin, Josephine R.,Karanam, Bindhu V.,Vincent, Stella H.,Cheng, Kang,Goulet, Mark T.
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p. 827 - 832
(2007/10/03)
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- Nonlinear optical chromophores with isoquinolines, thieno[2,3-c]-pyridines and 2-(2′-thienyl)pyridines as inherently polarized π-electron bridges
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The synthesis and first hyperpolarizabilities of a series of isoquinolines and isoquinolinium salts, and also thienopyridines, thienylpyridines, and the corresponding pyridinium salts, determined by hyper-Rayleigh scattering in solution at 1064 and 1300 nm, are reported. These chromophores exhibit markedly high β values. Some of them show absorption maxima well below 400 nm, enabling their use in blue transparent frequency doubling devices. We have performed X-ray structure analyses for thienopyridines 13a,c.
- Nerenz, Heiko,Meier, Martin,Grahn, Walter,Reisner, Axel,Schmaelzlin, Elmar,Stadler, Stefan,Meerholz, Klaus,Braeuchle, Christoph,Jones, Peter G.
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p. 437 - 447
(2007/10/03)
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- Fluorescence of Amphiphilic Hemicyanine Dyes without Free Double Bonds
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Amphiphilic hemicyanine dyes were obtained by coupling unpolar derivatives of aniline and naphthylamine, respectively, to polar derivatives of pyridinium and isoquinolinium, respectively.These dyes have no free double bond that is prone to photoisomerization.They are effective voltage-sensitive probes in biomembranes.The dyes were characterized by their spectra of absorption and by the spectra, the quantum yields, and the lifetimes of fluorescence. (i) An enhanced polarity of solvents shifts the absorption to the blue and the fluorescence to the red.The solvatochromism is described by an enhancement of the Stokes shift at an invariant 00 energy. (ii) An enhanced polarity lowers the quantum yield of fluorescence by orders of magnitude.The effect is described by an enhancement of nonradiative deactivation at an invariant radiative decay.The enhancements of the Stokes shift and of the nonradiative decay are assigned to two types of intramolecular charge-transfer that couple to polar solvents.The first one is induced by electronic excitation.The second one is induced by intramolecular twist in the excited state.The properties of the dyes in amphiphilic assemblies are discussed in terms of their properties in bulk solvents.
- Ephardt, Heinz,Fromherz, Peter
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p. 4540 - 4547
(2007/10/02)
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- Synthesis of Isoquinolines from Indenes
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A general procedure for the synthesis of isoquinolines from appropriately substituted indenes is described.Ozonolysis of the indenes followed by reductive workup gives intermediate homophthalaldehydes which are treated with ammonium hydroxide to give the isoquinolines.This "one-pot", three-step reaction sequence was applied to the formation of all of the mono-C-methyl-substituted isoquinolines in a regiospecific manner.The procedure is applicable to both electron-withdrawing and electron-donating substituents on the indene system.In this manner the 6- and 7-nitro-,-bromo-, and -iodoisoquinolines were prepared.
- Miller, R. Bryan,Frincke, James M.
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p. 5312 - 5315
(2007/10/02)
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