- Aminoquinoline-rhodium(II) conjugates as src-family SH3 ligands
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High-affinity, selective ligands are sought for a variety of biomolecules but are particularly difficult to generate in the protein-protein interaction space. Rhodium(II) conjugates provide a structure-based approach to improved affinity and specificity f
- Martin, Samuel C.,Ball, Zachary T.
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Read Online
- Selectfluor-mediated regioselective nucleophilic functionalization of N-heterocycles under metal- and base-free conditions
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A practical and environmentally attractive methodology for the direct diversification of N-heterocycles at ambient temperature under open-air conditions was developed. The obvious advantage of the process is that no toxic reagent, transition metal, base or other additive is employed, thus greatly reducing costs, facilitating post-reaction neutralization and purification and minimizing the environmental impact.
- Xie, Long-Yong,Qu, Jie,Peng, Sha,Liu, Kai-Jian,Wang, Zheng,Ding, Man-Hua,Wang, Yi,Cao, Zhong,He, Wei-Min
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Read Online
- Efficient visible light mediated synthesis of quinolin-2(1H)-ones from quinolineN-oxides
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Quinolin-2(1H)-ones are one of the important classes of compounds due to their prevalence in natural products and in pharmacologically useful compounds. Here we present an unconventional and hitherto unknown photocatalytic approach to their synthesis from easily available quinoline-N-oxides. This reagent free highly atom economical photocatalytic method, with low catalyst loading, high yield and no undesirable by-product, provides an efficient greener alternative to all conventional synthesis reported to date. The robustness of the methodology has been successfully demonstrated with easy scaling up to the gram scale.
- Bhuyan, Samuzal,Chhetri, Karan,Hossain, Jagir,Jana, Saibal,Mandal, Susanta,Roy, Biswajit Gopal
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supporting information
p. 5049 - 5055
(2021/07/29)
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- Scalable and Practical Synthesis of Halo Quinolin-2(1H)-ones and Quinolines
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A practical and scalable synthesis of halo quinolin-2(1H)-ones is presented. The heterocycles are easily accessed from inexpensive halo anilines in a two-step sequence. The anilines are acylated with methyl 3,3-dimethoxypropionate under basic conditions in quantitative yields. The crude amides undergo cyclization in sulfuric acid to the desired halo quinolin-2(1H)-ones in 28-93% yield (2 steps). The synthetic sequence was successfully applied on 800 g scale. Anilines with strong electron withdrawing or electron donating groups were poor substrates for this procedure. 6-Iodoquinolin-2(1H)-one and 6-bromo-8-iodoquinolin-2(1H)-one were further functionalized to obtain quinolines substituted with various functional groups.
- Zaugg, Cornelia,Schmidt, Gunther,Abele, Stefan
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supporting information
p. 1003 - 1011
(2017/07/26)
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- A nitrogen oxide C2 - bit hydroxylated method (by machine translation)
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The present invention relates to nitrogen oxide C2 - bit hydroxylated method, in particular under reflux conditions in dichloroethane, three pyrrole alkyl bromide (PyBrop) [...] phosphate, sodium acetate, water and nitrogen oxides produced by the reaction of hydroxyl-substituted product. The process has simple operation, mild condition, high reaction selectivity, substrate wide applicability, high yield and the like. The application for the first time using this method to synthesize a series of 2 - hydroxyquinoline, 2 - hydroxy pyridine and 1 - hydroxy isoquinoline compound, in the establishment of the compounds of the library synthesis application have broad prospects. (by machine translation)
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Paragraph 0031; 0032; 0033; 0034; 0035; 0036-0038; 0063-0068
(2017/05/19)
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- Practical route to 2-quinolinones via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade reaction
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Quinolinone derivatives were constructed via a Pd-catalyzed C-H bond activation/C-C bond formation/cyclization cascade process with simple anilines as the substrates. This finding provides a practical procedure for the synthesis of quinolinone-containing alkaloids and drug molecules. The utility of this method was demonstrated by a formal synthesis of Tipifarnib.
- Wu, Junliang,Xiang, Shaohua,Zeng, Jing,Leow, Minli,Liu, Xue-Wei
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supporting information
p. 222 - 225
(2015/01/30)
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- Synthesis and biological evaluation of 2-substituted quinoline 6-carboxamides as potential mGluR1 antagonists for the treatment of neuropathic pain
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A series of 2-amino and 2-methoxy quinoline-6-carboxamide derivatives have been synthesized and their metabotropic glutamate receptor type 1 (mGluR1) antagonistic activities were evaluated in a functional cell-based assay. The compound 13c showed the highest potency with IC50 value of 2.16μM against mGluR1. Finally, in vivo evaluation of 13c in the rat spinal nerve ligation (SNL) model exhibited weak analgesic effects with regard to both mechanical allodynia and cold allodynia.
- Kim, Younghee,Son, Jiwon,Kim, Juhyeon,Baek, Du-Jong,Lee, Yong Sup,Lim, Eun Jeong,Lee, Jae Kyun,Pae, Ae Nim,Min, Sun-Joon,Cho, Yong Seo
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p. 508 - 518
(2014/07/08)
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- Manganese(III)-mediated direct Csp2-H radical trifluoromethylation of coumarins with sodium trifluoromethanesulfinate
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Mn(OAc)3-mediated direct Csp2-H radical trifluoromethylation of coumarins with CF3SO2Na (Langlois reagent) to afford selective 3-trifluoromethyl coumarins in moderate to good yields is described. This methodology can also be applied to the trifluoromethylation of quinolinones and pyrimidinones. The Royal Society of Chemistry 2014.
- Cao, Xiao-Hui,Pan, Xiangqiang,Zhou, Peng-Jun,Zou, Jian-Ping,Asekun, Olayinka Taiwo
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supporting information
p. 3359 - 3362
(2014/03/21)
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- ROR MODULATORS AND THEIR USES
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The invention relates to ROR modulators; compositions comprising an effective amount of a ROR modulator; and methods for treating or preventing diseases associated with ROR.
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- URACIL OR THYMINE DERIVATIVE FOR TREATING HEPATITIS C
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Present application relates to the compounds of formula I useful to treat hepatitis C (HCV) infections. In the structure of the disclosed compounds is the uracil or thymine derivative linked via a phenylene into either fused 2-ring cyclic system (R6) or alternatively via additional two-atom linker (L) to a 5-6 membered monocycle (R6). Application further discloses polymorphs and pseudopolymorphs of two specific compounds: N-(6(3-t-butyl-5-(2>4-dioxo-3,4-dihydropyrimidin-1 (2H)- y!)2-methoxy-phenyl)naphthalen-2-yl)methanesulfonamide and (E)-N-(4(3-t- butyl-5-(2,4-dioxo-3)4-dihydropyrimidin-1 (2H)-yl)2-methoxy-styryl- phenyl)methanesulfonamide.
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Page/Page column 181
(2009/04/25)
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- ANTI-INFECTIVE PYRIMIDINES AND USES THEREOF
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This invention relates to: (a) compounds and salts thereof that, inter alia, inhibit HCV; (b) intermediates useful for the preparation of such compounds and salts; (c) compositions comprising such compounds and salts; (d) methods for preparing such intermediates, compounds, salts, and compositions; (e) methods of use of such compounds, salts, and compositions; and (f) kits comprising such compounds, salts, and compositions.
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Page/Page column 110
(2009/04/25)
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- A general synthesis of quinolinones and benzothiazine 1,1-dioxides via ring closing metathesis
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A general synthesis of quinolinones and benzothiazine 1,1-dioxides is presented. A series of N-phenylacrylamides and N-phenylethylenesulfonamides were studied for their ability to undergo ring closing methathesis to yield the corresponding quinolinones and benzothiazine 1,1-dioxides, respectively. The reactions are general in scope and represents a mild method for the preparation of these heterocycles.
- Minville, Joannie,Poulin, Jason,Dufresne, Claude,Sturino, Claudio F.
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p. 3677 - 3681
(2008/09/20)
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- First synthesis of 3,6′- and 3,7′-biquinoline derivatives
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The preparation of new 3,6′- and 3,7′-biquinoline derivatives was achieved by microwave-assisted Suzuki cross-coupling between N-protected 6- or 7-bromoquinolin-2(lH)-ones and quino-lin-3-ylboronic acid. Moreover, a new synthesis of 7-bromoquino-lin-2(lH)-one leading solely to the 7-substituted isomer was carried out. Thieme Stuttgart.
- Broch, Sidonie,Anizon, Fabrice,Moreau, Pascale
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body text
p. 2039 - 2044
(2009/04/03)
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- NOVEL CHEMICAL COMPOUNDS
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This invention relates to newly identified compounds for inhibiting hYAK3 proteins and methods for treating diseases associated with hYAK3 activity.
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Page/Page column 35-36
(2010/11/25)
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- Development of 6-substituted indolylquinolinones as potent Chek1 kinase inhibitors
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Through a comparison of X-ray co-crystallographic data for 1 and 2 in the Chek1 active site, it was hypothesized that the affinity of the indolylquinolinone series (2) for Chek1 kinase would be improved via C6 substitution into the hydrophobic region I (HI) pocket. An efficient route to 6-bromo-3-indolyl-quinolinone (9) was developed, and this series was rapidly optimized for potency by modification at C6. A general trend was observed among these low nanomolar Chek1 inhibitors that compounds with multiple basic amines, or elevated polar surface area (PSA) exhibited poor cell potency. Minimization of these parameters (basic amines, PSA) resulted in Chek1 inhibitors with improved cell potency, and preliminary pharmacokinetic data are presented for several of these compounds.
- Huang, Shaei,Garbaccio, Robert M.,Fraley, Mark E.,Steen, Justin,Kreatsoulas, Constantine,Hartman, George,Stirdivant, Steve,Drakas, Bob,Rickert, Keith,Walsh, Eileen,Hamilton, Kelly,Buser, Carolyn A.,Hardwick, James,Mao, Xianzhi,Abrams, Marc,Beck, Steve,Tao, Weikang,Lobell, Rob,Sepp-Lorenzino, Laura,Yan, Youwei,Ikuta, Mari,Murphy, Joan Zugay,Sardana, Vinod,Munshi, Sanjeev,Kuo, Lawrence,Reilly, Michael,Mahan, Elizabeth
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p. 5907 - 5912
(2007/10/03)
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- 2-(4-Alkylpiperazin-1-yl)quinolines as a new class of imidazole-free histamine H3 receptor antagonists
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With the aim of identifying structurally novel, centrally acting histamine H3 antagonists, a series of 2-(4-alkylpiperazin-1-yl)quinolines was prepared. Systematic variation of the substituents led to highly potent histamine H3 antagonists with low polar surface area and appropriate log P for blood-brain barrier penetration.
- Zaragoza, Florencio,Stephensen, Henrik,Peschke, Bernd,Rimvall, Karin
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p. 306 - 311
(2007/10/03)
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- Alkyne compounds with MCH antagonistic activity and medicaments comprising these compounds
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The present invention relates to alkyne compounds of general formula I wherein the groups and residues A, B, W, X, Y, Z, R1 and R2 have the meanings given in claim 1. The invention further relates to pharmaceutical compositions containing at least one alkyne according to the invention. In view of their MCH-receptor antagonistic activity the pharmaceutical compositions according to the invention are suitable for the treatment of metabolic disorders and/or eating disorders, particularly obesity, bulimia, anorexia, hyperphagia and diabetes.
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- Novel aryl- and heteroarylpiperazines
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Novel aryl- and heteroarylpiperazines, use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds, and a method of treatment employing these compounds and compositions. The compounds show a high and selective binding affinity to the histamine H3 receptor indicating histamine H3 receptor antagonistic, inverse agonistic or agonistic activity. As a result, the compounds are useful for the treatment of diseases and disorders related to the histamine H3 receptor.
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- Inhibitors of factor Xa
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Novel compounds, their salts and compositions related thereto having activity against mammalian factor Xa are disclosed. The compounds of formula (I) below: are useful in vitro or in vivo for preventing or treating coagulation disorders.
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- 6-Substituted 1H-quinolin-2-ones and 2-methoxy-quinolines: Synthesis and evaluation as inhibitors of steroid 5α reductases types 1 and 2
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A Negishi-type coupling reaction between 6-bromo-2-methoxyquinoline. (1a) and various 4-bromo-N,N'dialkyl-benzamides gave access to 6-substituted 2-methoxy-quinolines 1-3 and 1H-quinolin-2-ones 4-12. Most of these compound proved to be inhibitors of steroid 5α reductases with activity arid selectivity both being strongly dependent on the features of the heterocycle and the size of the N,N-dialkylamide substituent. The most active inhibitor for the human type 2 isozyme was 6-[4-(N,N-diisopropylcarbamoyl)phenyl]-1H-quinolin-2-one 4 (K(i) 800 ± 85 nM), showing mostly competitive inhibitory patterns. A type 1 selective inhibitor could be identified with 6-[4-(N,N-diisopropylcarbamoyl)phenyl]-N-methyl-quinolin-2-one (5, IC50 510 nM). (C) 2000 Editions scientifiques et medicales Elsevier SAS.
- Baston, Eckhard,Palusczak, Anja,Hartmann, Rolf W.
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p. 931 - 940
(2007/10/03)
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- Synthesis, SAR and in vivo activity of novel thienopyridine sulfonamide pyrrolidinones as factor Xa inhibitors
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Thienopyridine sulfonamide pyrrolidinones were found to be potent and selective inhibitors of the coagulation cascade enzyme factor Xa. SAR studies led to several compounds that were selected for further in vivo investigation. These novel aryl binding pocket moieties represent a structural modification to a series of fXa inhibitors. Several compounds proved to be efficacious iv antithrombotic agents.
- Becker, Michael R.,Ewing, William R.,Davis, Roderick S.,Pauls, Henry W.,Ly, Cuong,Li, Aiwen,Mason, Helen J.,Choi-Sledeski, Yong Mi,Spada, Alfred P.,Chu, Valeria,Brown, Karen D.,Colussi, Dennis J.,Leadley, Robert J.,Bentley, Ross,Bostwick, Jeff,Kasiewski, Charles,Morgan, Suzanne
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p. 2753 - 2758
(2007/10/03)
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- Regioselective Alkoxydehalogenation of 2,4-Dihalogenoquinolines and a Reinvestigation of the Bromination of 2-Methoxyquinoline
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Regioselective alkoxydehalogenation of 2,4-dichloro- and 2,4-dibromo-quinoline with solid sodium alkoxide in toluene gives the 2-alkoxy-4-halogenoquinolines 7-10, identified by 1H and 13C NMR spectroscopy.Bromination of 2-methoxyquinoline occurs at the 6- and 8-positions and does not give the 4-bromo derivative as originally reported.
- Osborne, Alan G.,Miller, Luke A. D.
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p. 181 - 184
(2007/10/02)
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- Pesticides
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Compound of the formula (I) are disclosed or a salt thereof, wherein Ar is an optionally substituted polycyclic ring system containing n rings, where n is the integer 2 or 3, at least n-1 rings being aromatic and containing one to three ring nitrogen atoms and optionally containing one or more additional heteroatoms; Q is an alkyl chain containing 1 to 12 carbon atoms and optionally containing a sulphur or one or two oxygen atoms; Q1 is a group (C(R2)=C(R3))a --(C(R4)=C(R5)) wherein a is 0 or 1, R2, R3, R4 and R5 are the same or different, at least two being hydrogen and the other two being independently selected from hydrogen, halo, C1-4 haloalkyl; X is oxygen or sulphur; and R1 is selected from hydrogen and C1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C1-6 alkoxy are described which have activity particularly against arthropod pests. Pesticidal formulations containing the compounds of the formula (1), their use in the control of pests and method for their preparation are also disclosed.
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