- Structural-activity relationship study of highly-functionalized imidazolines as potent inhibitors of nuclear transcription factor-κB mediated IL-6 production
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We herein describe the synthesis and anti-inflammatory properties of a small library of imidazoline-based NF-κB inhibitors. The structure-activity relationship of various substituents on an imidazoline core structure was evaluated for the ability to inhibit NF-κB mediated IL-6 production. Optimization of the scaffolds was pursued by correlating luciferase-based NF-κB reporter assays with inhibition of IL-6 production in IL-1β stimulated human blood. Several derivatives were found to inhibit NF-κB mediated IL-6 production in the nanomolar range in IL-1β stimulated human blood.
- Kahlon, Daljinder K.,Lansdell, Theresa A.,Fisk, Jason S.,Tepe, Jetze J.
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- Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives
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We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.
- Metrano, Anthony J.,Miller, Scott J.
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p. 1542 - 1554
(2014/03/21)
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- Organocatalytic oxyamination of azlactones: Kinetic resolution of oxaziridines and asymmetric synthesis of oxazolin-4-ones
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The first example of oxyamination of azlactones with oxaziridines was realized using a chiral bisguanidinium salt. Efficient catalytic asymmetric oxyamination and kinetic resolution of oxaziridines occurred simultaneously. Various chiral oxazolin-4-one derivatives with potential biological activity were obtained (up to 92% ee). Meanwhile, a series of optically pure oxaziridines were recovered with up to 99% ee and successfully used in the asymmetric oxyamination of 3-methyl-1H-indole and styrene. The triple stereodifferentiation process was also studied via control experiments.
- Dong, Shunxi,Liu, Xiaohua,Zhu, Yin,He, Peng,Lin, Lili,Feng, Xiaoming
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supporting information
p. 10026 - 10029
(2013/07/26)
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- One-pot preparation of oxazol-5(4H)-ones from amino acids in aqueous solvents
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A method for one-pot synthesis of oxazol-5(4H)-ones has been developed using 4-(4,6-dimethoxy-l,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), which is available for the activation of carboxylic acids in an aqueous solvent. The oxazolones were prepared by the TV-acylation of amino acids with carboxylic acids and the subsequent cyclodehydration of the resulting N-acylamino acids by the addition of N,N-diethylaniline. Since both these reactions proceed effectively with the same coupling reagent, DMT-MM, in aqueous solvents, the procedure is simplified and becomes easy to perform. In addition, 5-(triazinyloxy)oxazole derivatives have been synthesized by controlling the basicity of the reaction system.
- Fujita, Hikaru,Kunishima, Munetaka
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experimental part
p. 907 - 912
(2012/08/08)
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- Synthesis of 1,2,4-Triazolines and triazoles utilizing oxazolones
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We describe herein a convenient method for the synthesis of 1,2,4-triazolines using oxazolones and azodicarboxylates. Subsequent treatment of these 1,2,4-triazolines with NaOH provides efficient access to the corresponding triazoles.
- Saleem, Rahman Shah Zaib,Tepe, Jetze J.
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supporting information; experimental part
p. 4330 - 4332
(2010/09/03)
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- Multicomponent synthesis of highly substituted imidazolines via a silicon mediated 1,3-dipolar cycloaddition
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A diastereoselective multicomponent synthesis of highly functionalized imidazolines is reported. A silicon mediated 1,3 dipolar cycloaddition of the in situ generated münchnone with an imine resulted in the formation of highly substituted imidazolines. The imidazolines contain a four-point diversity and two stereocenters and the cycloaddition reaction is applicable to aryl, alkyl, acyl, and heterocyclic substitutions.
- Peddibhotla,Tepe
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p. 1433 - 1440
(2007/10/03)
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- AN EFFICIENT TRANSFORMATION OF N-ACYL-α-AMINO ACIDS INTO DIACYLAMINES VIA 2,4-DISUBSTITUTED OXAZOL-5(4H)-ONES
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Base-catalyzed oxygenative decarboxylation of a variety of 2,4-disubstituted oxazol-5(4H)-ones in benzene with triethylamine or in dimethylsulfoxide with potassium tert-butoxide gives diacylamines.KEYWORDS - base-catalyzed autooxidation; selective oxygenation; decarboxylation; oxazol-5(4H)-one; N-acyl-α-amino acid; diacylamine
- Suda, Kohji,Hino, Fumio,Yijima, Chino
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p. 882 - 885
(2007/10/02)
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