14113-01-0Relevant articles and documents
Water Content of Phospholipid Bilayers
Menger, F. M.,Aikens, P.,Wood M.
, p. 180 - 182 (1988)
13C N.m.r. data show that static water is absent at five locations along bilayer chains, in sharp contrast to the situation with micelles.
Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates
Mills, L. Reginald,Zhou, Cuihan,Fung, Emily,Rousseaux, Sophie A. L.
supporting information, p. 8805 - 8809 (2019/11/03)
Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.
Hetero-aromatic compound and its use in medicine
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Paragraph 1416; 1437-1440, (2019/07/04)
The invention provides a hetero-aromatic compound or a stereisomer, geometric isomer, tautomer, despinner, nitrogen oxide, hydrate, solvate, metabolite, metabolism precursor and pharmaceutically acceptable salt or prodrug thereof, which is used for treating proliferative diseases. The invention also discloses a pharmaceutical composition containing the compound and an application of the compound or pharmaceutical composition thereof in preparation of a medicine for treating proliferative diseases.
Validating Eaton's Hypothesis: Cubane as a Benzene Bioisostere
Chalmers, Benjamin A.,Xing, Hui,Houston, Sevan,Clark, Charlotte,Ghassabian, Sussan,Kuo, Andy,Cao, Benjamin,Reitsma, Andrea,Murray, Cody-Ellen P.,Stok, Jeanette E.,Boyle, Glen M.,Pierce, Carly J.,Littler, Stuart W.,Winkler, David A.,Bernhardt, Paul V.,Pasay, Cielo,De Voss, James J.,McCarthy, James,Parsons, Peter G.,Walter, Gimme H.,Smith, Maree T.,Cooper, Helen M.,Nilsson, Susan K.,Tsanaktsidis, John,Savage, G. Paul,Williams, Craig M.
supporting information, p. 3580 - 3585 (2016/03/23)
Pharmaceutical and agrochemical discovery programs are under considerable pressure to meet increasing global demand and thus require constant innovation. Classical hydrocarbon scaffolds have long assisted in bringing new molecules to the market place, but an obvious omission is that of the Platonic solid cubane. Eaton, however, suggested that this molecule has the potential to act as a benzene bioisostere. Herein, we report the validation of Eaton's hypothesis with cubane derivatives of five molecules that are used clinically or as agrochemicals. Two cubane analogues showed increased bioactivity compared to their benzene counterparts whereas two further analogues displayed equal bioactivity, and the fifth one demonstrated only partial efficacy. Ramifications from this study are best realized by reflecting on the number of bioactive molecules that contain a benzene ring. Substitution with the cubane scaffold where possible could revitalize these systems, and thus expedite much needed lead candidate identification.
Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2
Liu, Yu,Cornella, Josep,Martin, Ruben
supporting information, p. 11212 - 11215 (2014/09/30)
A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atmospheric pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids.
PYRIDIN-2YL SULFANYL ACID ESTERS AND PROCESS FOR THE PREPARATION THEREOF
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Paragraph 0091; 0127; 0128; 0129; 0130; 0131, (2013/06/04)
The present invention relates to Pyridin-2-yl sulfanyl acid ester compounds having antiinflammatory properties. The present invention particularly relates to novel anti-inflammatory heterocyclic acid esters of Pyridin-2-yl sulfanyl having the structure of general formula 1 which have been screened for their antiinflammatory activity with respect to inhibition of adhesion of neutrophils, isolated from human peripheral blood, onto the surface of human umbilical vein endothelial cells (HU-VEC) as a result of inhibition of the cytokine-stimulated expression of cell adhesion molecule ICAM-1. The compound RS—Z, 3-(Pyridin-2-yl sulfanyl)-propionic acid pentyl ester (structure 1a, R1=H, R2=H, R3=CH2-COOC5H11) was found to be most effective for ICAM-1 and neutrophil adhesion inhibition and was found to effectively alleviate inflammation mediated by excessive leukocyte infiltration leading to inflammatory disorders or like conditions, such as acute lung injury and acute respiratory distress syndrome in mice.
PYRIDIN- 2 - YL SULFANYL ACID ESTERS AND PROCESS FOR THE PREPARATION THEREOF
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Page/Page column 11-12; 14, (2012/02/05)
The present invention relates to Pyridin-2-yl sulfanyl acid ester compounds having antiinflammatory properties. The present invention particularly relates to novel anti-inflammatory heterocyclic acid esters of Pyridin-2-yl sulfanyl having the structure of general formula 1 which have been screened for their antiinflammatory activity with respect to inhibition of adhesion of neutrophils, isolated from human peripheral blood, onto the surface of human umbilical vein endothelial cells (HUVEC) as a result of inhibition of the cytokine-stimulated expression of cell adhesion molecule ICAM-1. The compound RS-Z, 3-(Pyridin-2-yl sulfanyl)-propionic acid pentyl ester (structure la, R1 = H, R2 = H, R3 = CH2COOC5H11) was found to be most effective for ICAM-1 and neutrophil adhesion inhibition and was found to effectively alleviate inflammation mediated by excessive leukocyte infiltration leading to inflammatory disorders or like conditions, such as acute lung injury and acute respiratory distress syndrome in mice.
Influence of positional isomers on the macroscale and nanoscale architectures of aggregates of racemic hydroxyoctadecanoic acids in their molecular gel, dispersion, and solid states
Abraham, Shibu,Lan, Yaqi,Lam, Ricky S. H.,Grahame, Douglas A. S.,Kim, Jennifer Jae Hee,Weiss, Richard G.,Rogers, Michael A.
experimental part, p. 4955 - 4964 (2012/07/13)
Inter/intramolecular hydrogen bonding of a series of hydroxystearic acids (HSAs) are investigated. Self-assembly of molecular gels obtained from these fatty acids with isomeric hydroxyl groups is influenced by the position of the secondary hydroxyl group. 2-Hydroxystearic acid (2HSA) does not form a molecular dimer, as indicated by FT-IR, and growth along the secondary axis is inhibited because the secondary hydroxyl group is unable to form intermolecular H-bonds. As well, the XRD long spacing is shorter than the dimer length of hydroxystearic acid. 3-Hydroxystearic acid (3HSA) forms an acyclic dimer, and the hydroxyl groups are unable to hydrogen bond, preventing the crystal structure from growing along the secondary axis. Finally, isomers 6HSA, 8HSA, 10HSA, 12HSA, and 14HSA have similar XRD and FT-IR patterns, suggesting that these molecules all self-assemble in a similar fashion. The monomers form a carboxylic cyclic dimer, and the secondary hydroxyl group promotes growth along the secondary axis.
Synthesis, biological evaluation, and molecular docking of Ugi products containing a zinc-chelating moiety as novel inhibitors of histone deacetylases
Grolla, Ambra A.,Podestà, Valeria,Chini, Maria Giovanna,Di Micco, Simone,Vallario, Antonella,Genazzani, Armando A.,Canonico, Pier Luigi,Bifulco, Giuseppe,Tron, Gian Cesare,Sorba, Giovanni,Pirali, Tracey
experimental part, p. 2776 - 2785 (2010/02/28)
HDAC inhibitors show great promise for the treatment of cancer. As part of a broader effort to explore the SAR of HDAC inhibitors, synthesis, biological evaluation, and molecular docking of novel Ugi products containing a zinc-chelating moiety are presented. One compound shows improved inhibitory potencies compared to SAHA, demonstrating that hindered lipophilic residues grafted on the peptide scaffold of the α-aminoacylamides can be favorable in the interaction with the enzyme.
Sodium ion internalized within phospholipid membranes
Menger, Fredric M.,Galloway, Ashley L.,Chlebowski, Mary E.,Wu, Shaoxing
, p. 14034 - 14035 (2007/10/03)
Seven phospholipids, modified with ester groups in their hydrophobic chains, were synthesized and examined for their ability to promote sodium ion flux across vesicular membranes. It was found by 23Na NMR that only the phospholipids having short chain segments beyond their terminal ester groups catalyze sodium ion transfer by up to 2 orders of magnitude relative to a conventional phospholipid, POPC. The rates increase with the concentration of the ester-phospholipid admixed with POPC in the bilayer. More surprisingly, the rates increase with the time allowed for the vesicles to age. This was attributed to ester-phospholipid migrating in the bilayers to form domains that solubilize the sodium ion within the hydrocarbon interior of the membrane. Such membrane domains explain why shift reagent-modified NMR spectra display three 23Na signals representing sodium outside the vesicles, sodium within the vesicular water pools, and sodium within the membranes themselves. Copyright
