4841-84-3Relevant articles and documents
A diastereoselective P450-catalyzed epoxidation reaction: Anti versus syn reactivity This Letter is dedicated to the memory of Harry Wasserman
Ilie, Adriana,Lonsdale, Richard,Agudo, Rubén,Reetz, Manfred T.
, p. 3435 - 3437 (2015)
The achiral cyclohexene derivative dimethyl cis-1,2,3,6-tetrahydrophthalate has been subjected to oxidation catalyzed by cytochrome P450 monooxygenase P450-BM3, leading to diastereoselective epoxidation rather than oxidative hydroxylation. This reaction occurs with 94% diastereoselectivity in favor of the anti-epoxide, in contrast to m-CPBA which delivers unselectively a 70:30 mixture of anti/syn diastereomers. The experimental results are nicely explained on a molecular level by docking experiments and molecular dynamics computations.
Novel easily accessible glucosidase inhibitors: 4-hydroxy-5-alkoxy-1,2-cyclohexanedicarboxylic acids
Brazdova, Barbora,Tan, Nikmala S.,Samoshina, Nataliya M.,Samoshin, Vyacheslav V.
, p. 311 - 321 (2009)
Glycosidases are very important enzymes involved in a variety of biochemical processes with a special importance to biotechnology, food industry, and pharmacology. Novel structurally simple inhibitors derived from cyclohexane-1,2-dicarboxylic acids were s
Novel 1,2,3-triazole compounds: Synthesis, In vitro xanthine oxidase inhibitory activity, and molecular docking studies
Tan, Ayse
, (2020)
In this study, novel 1,2,3-triazole compounds containing carbasugar frameworks (5 and 6) were synthesized by the copper-catalyzed azide-alkyne cycloaddition reactions and their in vitro inhibition effects on the enzyme xanthine oxidase were investigated. All of the synthesized compounds were characterized by spectroscopic methods. According to the enzyme inhibition results, compounds 5 (IC50 = 0.586 ± 0.017 μM) and 6 (IC50 = 0.751 ± 0.021 μM) showed stronger inhibition effects than allopurinol (IC50 = 1.143 ± 0.019 μM), which is a standard drug used for inhibition of xanthine oxidase. The binding modes of the 1,2,3-triazole compounds (5 and 6) with the active site of xanthine oxidase were explained based on molecular docking studies. The molecular docking studies showed that the aromatic structure, π-π interactions and hydrophobic interactions play a major role in xanthine oxidase inhibition for compounds 5 and 6.
Diastereoselective cis to trans desymmetrization of dimethyl succinates
Michieletto, Ivan,Fabris, Fabrizio,De Lucchi, Ottorino
, p. 2505 - 2509 (1999)
Meso-succinates, readily available by Diels-Alder cycloaddition of dimethyl maleate or maleic anhydride followed by esterification, can be isomerized quantitatively from the cis to the trans isomers in the presence of lithium alkoxides. The reaction performed with enantiopure chiral lithium alkoxides yields diastereomeric trans-succinates in good yield and selectivity.
PHARMACEUTICAL COMPOUNDS FOR THE TREATMENT OF COMPLEMENT MEDIATED DISORDERS
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Page/Page column 299-300; 360-362, (2020/10/18)
This disclosure provides pharmaceutical compounds to treat medical disorders, such as complement-mediated disorders, including complement Cl -mediated disorders.
Trans-hydrogenation: Application to a concise and scalable synthesis of brefeldin a
Fuchs, Michael,Fürstner, Alois
supporting information, p. 3978 - 3982 (2015/03/30)
The important biochemical probe molecule brefeldin A (1) has served as an inspirational target in the past, but none of the many routes has actually delivered more than just a few milligrams of product, where documented. The approach described herein is clearly more efficient; it hinges upon the first implementation of ruthenium-catalyzed trans-hydrogenation in natural products total synthesis. Because this unorthodox reaction is selective for the triple bond and does not touch the transannular alkene or the lactone site of the cycloalkyne, it outperforms the classical Birch-type reduction that could not be applied at such a late stage. Other key steps en route to 1 comprise an iron-catalyzed reductive formation of a non-terminal alkyne, an asymmetric propiolate carbonyl addition mediated by a bulky amino alcohol, and a macrocyclization by ring-closing alkyne metathesis catalyzed by a molybdenum alkylidyne.
Chemoenzymatic Sequential Multistep One-Pot Reaction for the Synthesis of (1S,2R)-1-(Methoxycarbonyl)cyclohex-4-ene-2-carboxylic Acid with Recombinant Pig Liver Esterase
Süss, Philipp,Borchert, Sonja,Wardenga, Rainer,Hinze, Janine,Illner, Sabine,Von Langermann, Jan,Kragl, Udo,Bornscheuer, Uwe T.
, p. 2034 - 2038 (2016/02/26)
In this work, the development of a chemoenzymatic process for the production of (1S,2R)-1-(methoxycarbonyl)cyclohex-4-ene-2-carboxylic acid by ECS-PLE06 (recombinant pig liver esterase) is presented. Herein an optimized esterification protocol, starting f
Scale-up of a recombinant pig liver esterase-catalyzed desymmetrization of dimethyl cyclohex-4-ene-cis-1,2-dicarboxylate
Suess, Philipp,Illner, Sabine,Von Langermann, Jan,Borchert, Sonja,Bornscheuer, Uwe T.,Wardenga, Rainer,Kragl, Udo
, p. 897 - 903 (2014/08/05)
A recombinant isoenzyme of pig liver esterase was used for the highly enantioselective desymmetrization of dimethyl cyclohex-4-ene-cis-1,2- dicarboxylate. The selected recombinant esterase showed a significant advantage in enantioselectivity over the comm
Pre-organization of the core structure of E-selectin antagonists
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
supporting information; experimental part, p. 1342 - 1351 (2012/04/04)
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.
GLYCOMIMETIC-PEPTIDOMIMETIC INHIBITORS OF E-SELECTINS AND CXCR4 CHEMOKINE RECEPTORS
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Page/Page column 59, (2012/05/20)
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, glycomimetic-peptidomimetic compounds that inhibit both E-selectins and CXCR4 chemokine receptors are described.
