- Cinchona alkaloid derivative modified Fe3O4nanoparticles for enantioselective ring opening of: Meso -cyclic anhydrides
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In the present work, the molecular framework of quinidine was modified at the methoxy functional group of the C6′ carbon of the quinoline moiety with a long-chain carboxylic acid group (-COOH) and it was used as a capping agent during the synthesis of Fe3
- Soni, Hemant P.,Tomer, Sanjiv O.
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p. 2495 - 2507
(2022/02/11)
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- Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides
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A family of novel chloramphenicol base-amide organocatalysts possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.
- Xu, Lingjun,Han, Shuwen,Yan, Linjie,Wang, Haifeng,Peng, Haihui,Chen, Fener
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supporting information
p. 309 - 317
(2018/02/19)
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- Pre-organization of the core structure of E-selectin antagonists
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A new class of N-acetyl-dglucosamine (GlcNAc) mimics for Eselectin antagonists was designed and synthesized. The mimic consists of a cyclohexane ring substituted with alkyl substituents adjacent to the linking position of the fucose moiety. Incorporation into E-selectin antagonists led to the test compounds 8 and the 2'-benzoylated analogues 21, which exhibit affinities in the low micromolar range. By using saturation transfer difference (STD)-NMR it could be shown that the increase in affinity does not result from an additional hydrophobic contact of the alkyl substituent with the target protein E-selectin, but rather from a steric effect stabilizing the antagonist in its bioactive conformation. The loss of affinity found for antagonists 10 and 35 containing a methyl substituent in a remote position (and therefore unable to support to the stabilization of the core) further supports this hypothesis. Finally, when a GlcNAc mimetic containing two methyl substituents (52 and 53) was used, in which one methyl was positioned adjacent to the fucose linking position and the other was in a remote position, the affinity was regained.
- Schwizer, Daniel,Patton, John T.,Cutting, Brian,Smiesko, Martin,Wagner, Beatrice,Kato, Ako,Weckerle, Celine,Binder, Florian P. C.,Rabbani, Said,Schwardt, Oliver,Magnani, John L.,Ernst, Beat
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supporting information; experimental part
p. 1342 - 1351
(2012/04/04)
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- HETEROBIFUNCTIONAL INHIBITORS OF E-SELECTINS AND CXCR4 CHEMOKINE RECEPTORS
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Compounds, compositions and methods are provided for treating cancer and inflammatory diseases, and for releasing cells such as stem cells (e.g., bone marrow progenitor cells) into circulating blood and enhancing retention of the cells in the blood. More specifically, heterobifunctional compounds that inhibit both E-selectins and CXCR4 chemokine receptors are described.
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Page/Page column 12; 29-30
(2010/11/17)
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- Concise synthesis of the tricyclic core of platencin
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(Chemical Equation Presented) A radical change: Implementation of a radical-mediated rearrangement of the bicyclo[3.2.1]octyl moiety to the bicyclo-[2.2.2]octane structure has enabled a concise synthesis of the tricyclic core of platencin, a newly discove
- Yun, Sang Young,Zheng, Jun-Cheng,Lee, Daesung
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supporting information; experimental part
p. 6201 - 6203
(2009/04/06)
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- Methods of use of glycomimetics with replacements for hexoses and n-acetyl hexosamines
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Methods are provided for using a compound to treat, for example, endothelial dysfunction including vascular abnormalities. More specifically, methods are described for using an oligosaccharide compound or glycomimetic compound wherein a cyclohexane derivative is incorporated in either.
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Page/Page column 25; sheet1
(2008/12/08)
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- Cyclohexene derivative and method of producing the same
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Provided is a novel (1R, 2S)-1-acyl-2-carboxycyclohex-4-ene derivative represented by the following general formula [I], and its producing method, STR1 (where R1 represents a hydrogen atom, a lower alkyl group, or substituted or unsubstituted a
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- Towards the synthesis of HIV-protease inhibitors. Synthesis optically pure 3-carboxyl-decahydroisoquinolines
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The synthesis of optically pure decahydroisoquinoline 1, a component of HIV-protease inhibitors, was accomplished in 30-33% overall yield from the readily available optically pure monoacid 4.
- Houpis, Ioannis N.,Molina, Audrey,Reamer, Robert A.,Lynch, Joseph E.,Volante,Reider, Paul J.
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p. 2593 - 2596
(2007/10/02)
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- Enzyme-catalysed Asymmetric Synthesis, IV. - Synthesis of Homochiral Building Blocks for the Enantioselective Total Synthesis of Cyclopentanoids with an Esterase-catalysed Asymmetric Reaction as Key Step
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An efficient synthesis of the homochiral building blocks 2a and ent-2a based on the "enantiotopos-enzyme concept" for the total synthesis of cyclopentanoids is described.Key steps thereof are the almost quantitative PLE-catalysed asymmetric hydrolysis of the meso-diester 8 to the homochiral hemiester 9, whose absolute configuration was determined by crystal structure analysis of the (-)-ephedrine salt 12, the preparation of optically pure 9 and ent-9 by a racemate resolution of rac-9 using (+)- and (-)-ephedrine, the enantiodivergent synthesis of the lactones 18 and ent-18 from 9, as well as the enantioconvergent synthesis of 18 or ent-18 from 9 and ent-9 by optional chemoselective reduction of the ester and carboxy group, and finally the regioselective Dieckmann cyclisation of the isomeric diesters 23b/24b and ent-23b/ent-24b, respectively, to give the cyclopentanoid target compounds 2a and ent-2a.The structures of 23b, 24b, rac-2b, and rac-29 were determined by INADEQUATE-13C-NMR experiments.Dieckmann cyclisation of the trans-diester rac-31 also leads to rac-2a and rac-26a.
- Gais, Hans-Joachim,Lukas, Karl L.,Ball, Walter A.,Braun, Siegmar,Lindner, Hans J.
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p. 687 - 716
(2007/10/02)
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