33878-99-8Relevant articles and documents
Antibody-catalyzed enantioselective Robinson annulation
Zhong,Hoffmann,Lerner,Danishefsky,Barbas III
, p. 8131 - 8132 (1997)
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Proline mediated asymmetric ketol cyclization: A template reaction
Rajagopal,Moni,Subramanian,Swaminathan
, p. 1631 - 1634 (1999)
1H, 13C and ATR-FTIR Spectroscopic studies reveal that the asymmetric cyclization of prochiral triones 1 and 2 in the presence of S-proline is a template reaction.
Potent Anti-Inflammatory, Arylpyrazole-Based Glucocorticoid Receptor Agonists That Do Not Impair Insulin Secretion
Burke, Susan J.,Campagna, Shawn R.,Collier, J. Jason,Dunlap, Lee E.,Fisch, Alexander R.,Kennedy, Brandon J.,Kirkland, Justin K.,Lato, Ashley M.,Prevatte, Carson W.,Smith, Russell T.,Vogiatzis, Konstantinos D.
, p. 1568 - 1577 (2021/10/04)
Glucocorticoids (GCs) are widely used in medicine for their role in the treatment of autoimmune-mediated conditions, certain cancers, and organ transplantation. The transcriptional activities GCs elicit include transrepression, postulated to be responsible for the anti-inflammatory activity, and transactivation, proposed to underlie the undesirable side effects associated with long-term use. A GC analogue that could elicit only transrepression and beneficial transactivation properties would be of great medicinal value and is highly sought after. In this study, a series of 1-(4-substituted phenyl)pyrazole-based GC analogues were synthesized, biologically screened, and evaluated for SARs leading to the desired activity. Activity observed in compounds bearing an electron deficient arylpyrazole moiety showed promise toward a dissociated steroid, displaying transrepression while having limited transactivation activity. In addition, compounds 11aa and 11ab were found to have anti-inflammatory efficacy comparable to that of dexamethasone at 10 nM, with minimal transactivation activity and no reduction of insulin secretion in cultured rat 832/13 beta cells.
Assessing the Recyclability of Supramolecularly Assembled Organocatalytic Species: A Theoretical Insight
Llorens, Lluis,Llanes, Patricia,Fianchini, Mauro,Pericàs, Miquel A.
, p. 475 - 484 (2020/03/19)
Asymmetric organocatalytic synthesis is a powerful tool in organic chemistry to achieve desired stereoisomers in high purity via mild catalytic routes. The immobilization of homogeneous catalytic species onto heterogeneous phases embodies the evolution of asymmetric catalysis, since it allows the recycling of the catalyst for several runs until degradation. Previously reported non-covalent immobilization of proline-based catalysts for aldol reaction onto magnetic nanoparticles functionalized with β-cyclodextrin (MNP-β-CB) demonstrated the viability of the methodology. This paper proposes two new catalyst recycling strategies based on Cucurbit[7]uril (CB[7]) for the aldol reaction and the Robinson annulation. These recycling methodologies are conceptually different. The former relies on the homogeneous encapsulation of the catalyst in cucurbituril, CB[7] ? Cat, and its recycling in the aqueous phase by extraction of the aldol product with organic solvents. The latter relies on the heterogeneous encapsulation of the catalyst as MNP-CB[7] ? Cat2 system and its recycling by magnetic harvesting. Density functional theory (DFT) calculations have been employed to rationalize the thermodynamics of experimental results, and to suggest caveats and plausible improvements in view of a future catalytic design.