- QUINOLINE AND QUINAZOLINE COMPOUNDS AND METHODS OF USE THEREOF
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Compounds and methods for their preparation and use as therapeutic or prophylactic agents, fo example for treatment of cancer, bacterial or viral diseases by targeting Ectonucleotide Pyrophosphatase/Phosphodiesterase- 1 (ENPP1).
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Paragraph 00456-00457
(2020/10/09)
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- [1,2,4]TRIAZOLO[1,5-A]PYRIMIDINE COMPOUNDS AND USE IN STABILIZING MICROTUBULES
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The present disclosure provides compounds of formula (I) or (II) or a pharmaceutically acceptable salt or stereoisomer thereof, wherein Rx-R8 are defined herein. Also provided are compositions comprising a compound described herein and a pharmaceutically effective excipient, methods of stabilizing microtubules in a patient comprising administering to the patient a microtubule-stabilizing amount of a compound described herein, methods of treating cancer in a patient comprising administering to the patient a therapeutically effective amount of a compound described herein, and methods of treating a neurodegenerative disease in a patient comprising administering to the patient a therapeutically effective amount of a compound described herein.
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Paragraph 00141; 00142; 00144
(2019/09/18)
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- Synthesis of α-aminocarbonyl compounds via hetero dielsalder reaction
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A synthetic route to α-aminoketone derivatives via a hetero DielsAlder reaction is described. Diacylhydrazine was oxidized by tert-butyl hypochlorite in the presence of pyridine. After evaporation, the hetero DielsAlder reaction with diene was carried out without isolation of the azodicarbonyl compound. Quantitative hetero DielsAlder reaction was possible with 1 equivalent of diene when Hf(OTf)4 or AgOTf was used as the catalyst. The NN bond of the product was cleaved by SmI2-reduction in the presence of tert-BuOH in THF. Further, ozonolysis of the C=C double bond afforded the α-aminoketone derivative in excellent yield.
- Sakurai, Masayoshi,Kihara, Nobuhiro,Watanabe, Nobuhiro,Ikari, Yoshihiro,Takata, Toshikazu
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p. 144 - 147
(2018/01/01)
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- Design, synthesis and evaluation of photoactivatable derivatives of microtubule (MT)-active [1,2,4]triazolo[1,5-a]pyrimidines
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The [1,2,4]triazolo[1,5-a]pyrimidines comprise a promising class of non-naturally occurring microtubule (MT)-active compounds. Prior studies revealed that different triazolopyrimidine substitutions can yield molecules that either promote MT stabilization or disrupt MT integrity. These differences can have important ramifications in the therapeutic applications of triazolopyrimidines and suggest that different analogues may exhibit different binding modes within the same site or possibly interact with tubulin/MTs at alternative binding sites. To help discern these possibilities, a series of photoactivatable triazolopyrimidine congeners was designed, synthesized and evaluated in cellular assays with the goal of identifying candidate probes for photoaffinity labeling experiments. These studies led to the identification of different derivatives that incorporate a diazirine ring in the amine substituent at position 7 of the triazolopyrimidine heterocycle, resulting in molecules that either promote stabilization of MTs or disrupt MT integrity. These photoactivatable candidate probes hold promise to investigate the mode of action of MT-active triazolopyrimidines.
- Oukoloff, Killian,Kovalevich, Jane,Cornec, Anne-Sophie,Yao, Yuemang,Owyang, Zachary A.,James, Michael,Trojanowski, John Q.,Lee, Virginia M.-Y.,Smith, Amos B.,Brunden, Kurt R.,Ballatore, Carlo
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supporting information
p. 2180 - 2183
(2018/06/07)
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- Hexahydro-1 H -Isoindolinone-Like Scaffolds from Electronically Deactivated and Sterically Hindered Dienes: Synthesis in the Context of Muironolide A
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Initial synthetic efforts toward muironolide A based upon an intramolecular Diels-Alder strategy were hampered by a conjugate reduction rather than the desired half-reduction. An intermolecular Diels-Alder strategy was initiated that utilized electronically deactivated and sterically hindered dienes. The [4+2] cycloadditions were successful, but only with highly reactive dipolarophiles such as N-phenylmaleimide and 4-phenyl-1,2,4-triazoline-3,5-dione thus establishing the scope of these dienes. Although limited, installation of the α,β-unsaturated lactam embedded in the hexahydro-1H-isoindolinone is noteworthy.
- Olson, Christopher A.,Shaner, Courtnay E.,Roche, Sydney C.,Ferrence, Gregory M.,Mitchell, T. Andrew
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p. 2756 - 2766
(2015/09/15)
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- Enantioconvergent synthesis of (+)-aphanorphine via asymmetric pd-catalyzed alkene carboamination
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A concise asymmetric synthesis of (+)-aphanorphine has been achieved via a new enantioconvergent strategy. A racemic γ-aminoalkene derivative is transformed into a 1:1 mixture of enantiomerically enriched diastereomers using an asymmetric Pd-catalyzed car
- Mai, Duy N.,Rosen, Brandon R.,Wolfe, John P.
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supporting information; experimental part
p. 2932 - 2935
(2011/07/30)
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- Catalyst-controlled Wacker-type oxidation of protected allylic amines
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On the contrary: Utilizing the [Pd-(quinox)]-TBHP catalyst system, protected allylic amines were oxidized with high selectivity for the methyl ketone product. This is contrary to the results obtained by the substrate-controlled Tsuji-Wacker oxidation, which highlights the catalyst-controlled system presented here (see scheme). A variety of N-pro-tecting groups undergo selective oxidation with high ketone selectivity. TBHP = tert-butylhydroperoxide.
- Michel, Brian W.,McCombs, Jessica R.,Winkler, Andrea,Sigman, Matthew S.
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supporting information; experimental part
p. 7312 - 7315
(2010/11/05)
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- Microwave-assisted synthesis of novel (5-nitropyridin-2-yl)alkyl and (5-nitropyridin-3-yl)alkyl carbamates
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A straightforward approach to novel (5-nitropyridin-2-yl)alkyl and (5-nitropyridin-3-yl)alkyl carbamate building blocks is presented in this study. Their construction is achieved by condensation of N-carbamate a- and β-amino carbonyl derivatives with l-methyl-3,5-dinitro-2-pyridone 1 under microwave irradiation. Judiciously chosen modifications in the nature of the parent carbonyl starting material has influenced the regiochemical outcome of the reaction and allowed an efficient access to novel nitrogen-containing scaffolds. Compounds sharing morphological similarities have been gathered in three libraries differing from each other in a single structural parameter.
- Henry, Christophe,Haupt, Andreas,Turner, Sean C.
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supporting information; experimental part
p. 1932 - 1938
(2009/08/07)
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- A modular system for the preparation of diazirine-labeled mannose derivatives using thiourea bridging
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The protein FimH is a bacterial lectin, which is utilized by Escherichia coli to adhere to the glycocalyx of potential host cells. FimH has specificity for α-mannosyl residues, as revealed by biological as well as X-ray studies. To further investigate the
- Walter, Mark,Lindhorst, Thisbe K.
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p. 952 - 958
(2007/10/03)
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- DIPEPTIDYL PEPTIDASE-IV INHIBITING COMPOUNDS, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE AGENT
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The present invention relates to novel compounds exhibiting good inhibitory activity versus Dipeptidyl Peptidase-IV(DPP-IV), methods of preparing the same and pharmaceutical compositions containing the same as an active agent.
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Page/Page column 27
(2010/11/24)
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- The synthesis of a monoammonium derivative of fullerenopyrrolidine
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The Prato reaction was used to synthesize a monoammonium derivative of fullerenopyrrolidine.
- Kutyreva,Shchupak,Karnatsevich,Bazyakina,Suvorova
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p. 1535 - 1536
(2007/10/03)
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- Improved syntheses of α-BOC-aminoketones from α-BOC-amino-Weinreb amides using a pre-deprotonation protocol
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A general procedure was developed to prepare α-BOC-aminoketones in good yields from α-BOC-amino Weinreb amides containing an exchangeable amino proton. By first deprotonating this amino group using 1 equiv. of a simple alkyl Grignard base, only a stoichio
- Liu, Jinchu,Ikemoto, Norihiro,Petrillo, Daniel,Armstrong III, Joseph D.
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p. 8223 - 8226
(2007/10/03)
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- Enantioselective synthesis of β-hydroxy amines and aziridines using asymmetric transfer hydrogenation of α-amino ketones
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Enantioselective transfer hydrogenation of α-amino ketones is an effective method for the asymmetric synthesis of β-hydroxy amines and aziridines.
- Kawamoto,Wills
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p. 1916 - 1928
(2007/10/03)
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- A general synthesis of pyrroles and fused pyrrole systems from ketones and amino acids
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The lithium enolates of ketones react with BOC-α-amino aldehydes and BOC-α-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from α-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.
- Nagafuji, Pamela,Cushman, Mark
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p. 4999 - 5003
(2007/10/03)
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- An efficient synthesis of optically pure (R)- and (S)-2-(aminomethyl)alanine ((R)- and (S)-Ama) and (R)- and (S)-2-(aminomethyl)leucine ((R)- and (S)-Aml)
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An efficient synthesis of enantiomerically pure (R)- and (S)-2-(aminomethyl)alanine ((R)- and (S)-Ama) 1a and (R)- and (S)-2-(aminomethyl)leucine ((R)- and (S)-Aml) 1b is described. Resolution of the racemic amino acids was achieved using L-phenylalanine
- Obrecht,Karajiannis,Lehmann,Schonholzer,Spiegler,Muller
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p. 703 - 714
(2007/10/02)
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