67439-82-1Relevant academic research and scientific papers
IRAK DEGRADERS AND USES THEREOF
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Paragraph 3132; 3134, (2019/07/10)
The present invention provides compounds, compositions thereof, and methods of using the same.
Long hydrocarbon chain ether diols and ether diacids that favorably alter lipid disorders in vivo
Mueller, Ralf,Yang, Jing,Duan, Caiming,Pop, Emil,Lian, Hao Zhang,Huang, Tian-Bao,Denisenko, Anna,Denisko, Olga V.,Oniciu, Daniela C.,Bisgaier, Charles L.,Pape, Michael E.,Freiman, Catherine Delaney,Goetz, Brian,Cramer, Clay T.,Hopson, Krista L.,Dasseux, Jean-Louis H.
, p. 5183 - 5197 (2007/10/03)
Long hydrocarbon chain ethers with bis-terminal hydroxyl or carboxyl groups have been synthesized and evaluated for their potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes as well as for their effects on lipid and glycemic variables in female obese Zucker fatty rats following 1 and 2 weeks of daily oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ether functionality and the gem dimethyl or methyl/aryl substituents. Biological activity was found to be greatest for tetramethyl-substituted ether diols (e.g., 28 and 31), while bis(arylmethyl) derivatives (e.g., 10, 11, and 27), diethers (e.g., 49, 50, and 56), and diphenyl ethers (e.g., 35 and 36) were the least active. For the most biologically active compound 28, we observed as much as a 346% increase in serum HDL-cholesterol and a 71% reduction in serum triglycerides at the highest dose administered (100 mg/kg) after 2 weeks of treatment. For compound 31 we observed a 69% reduction in non-HDL-cholesterol, accompanied by a 131% increase in HDL-cholesterol and an 84% reduction in serum triglycerides under the same treatment conditions.
Design, synthesis, and characterization of peptide nanostructures having ion channel activity
Biron, Eric,Otis, Francois,Meillon, Jean-Christophe,Robitaille, Martin,Lamothe, Julie,Van Hove, Patrick,Cormier, Marie-Eve,Voyer, Normand
, p. 1279 - 1290 (2007/10/03)
We report the synthesis and the functional studies of multiple crown α-helical peptides designed to form artificial ion channels. The approach combines the versatility of solid phase peptide synthesis, the conformational predictability of peptidic molecul
Substituted diether diols by ring-opening of carbocyclic and stannylene acetals
Martinez-Bernhardt, Rolando,Castro, Peter P.,Godjoian, Gayane,Gutierrez, Carlos G.
, p. 8919 - 8932 (2007/10/03)
Reduction of malonaldehyde bis(ethylene and propylene acetals) with borane or monochloroborane produces diether diols 1 and 2 in high yield. Similar reduction of glyoxal his(ethylene acetals) has only limited utility for the preparation of tetrasubstituted triethylene glycols 3. Organotin chemistry is complementary: stannylene acetals prepared from disubstituted vicinal diols can be alkylated with half an equivalent of 1,2-dibromoethane to produce tetrasubstituted triethylene glycols 3, or with two equivalents of 2-chloroethanol to produce disubstituted triethylene glycols 4.
Molecular design of crown ethers. VII.1 syntheses and cation selectivities of unsubstituted 12- To 16-crown-4
Liu, Yu,Inoue, Yoshihisa,Hakushi, Tadao
, p. 3044 - 3046 (2007/10/02)
Solvent extraction of aqueous alkali and some heavy metal picrates with the title compounds showed that, with most cations except for Li+, Na+, and Ag+, the extractability decreases monotonically as the ring size increases from 12 to 16. However, 14-crown-4 showed the highest extractability and selectivity for Li+ over the larger alkali metals, while 15-crown-4 exhibited the highest Ag+/Tl+ selectivity.
Phase-Transfer-Catalyzed Synthesis of Oligoethylene Glycols and Derivatives
Bartsch, Richard A.,Cason, Victor C.,Czech, Bronislaw P.
, p. 857 - 860 (2007/10/02)
An efficient, two-step synthetic method for the addition of ethyleneoxy units to diols is reported.Reaction of HOROH with Cl(CH2CH2O)nTHP and 50percent aqueous NaOH in the presence of a phase-transfer catalyst gives THP(OCH2CH2)nORO(CH2CH2O)nTHP from which the protecting groups are readily removed to provide H(OCH2CH2)nORO(CH2CH2O)n in good-to-excellent yields.The influence of reactant diol structure upon yield has been determined.
A Convenient Synthesis of Substituted Polyether Diols
Castro, Peter P.,Tihomirov, Serge,Gutierrez, Carlos G.
, p. 5179 - 5181 (2007/10/02)
Alkyl-substituted polyether diols (or polythioether diols), which are potential precursors to substituted crown ethers, are produced in high yield by the selective reductive cleavage of C-O bonds in bis(cyclic acetals) by borane or monochloroborane.
SYNTHESIS AND ALKALI METAL CATION COMPLEXATION BY BENZOCROWN ETHERS
Czech, Bronislaw P.,Czech, Anna,Knudsen, Brian E.,Bartsch, Richard A.
, p. 717 - 722 (2007/10/02)
New or improved synthetic routes to several benzocrown ethers and alkali metal picrate extraction data for eight benzocrown ethers with varying sizes are reported.
Complexation and Solvent Extraction of Lithium Salts with 2,3,6,7,9,10-Hexahydro-5H-1,4,8,11-benzotetraoxacyclotridecin (Benzo-13-crown-4)
Olsher, Uriel,Jagur-Grodzinski, Joseph
, p. 501 - 505 (2007/10/02)
Solubility measurements were conducted in order to compare the affinity towards lithium salts of several 12- to 16-membered ring 'crown' ethers.The 13-membered ring benzo-13-crown-4 (L1) was found to be the most effective complexing agent for lithium among the investigated macrocyclic ethers.The effect of counter ions on the solubility was found to be OH(1-) 1 extract lithium salts selectively from aqueous solutions.In the latter solvent selectivity factor γ(Li(1+)/M(n+)) was found to be 2.5, 44, 216, and 355 for Na(1+), K(1+), Mg(2+), and Ca(2+) respectively.Hydrogen-1 n.m.r. measurements for the solutions of the lithium complexes of L1 indicate that a planar conformation of the quadridentate macrocyclic ring seems to be favoured in the complexed L1. The 1 : 1 complexes have been found to be dominant in all investigated solvent systems.However, in methylene chloride and in nitromethane the 2 : 1 'sandwich' type complexes could also be detected.The stability constants of the complexes were found to increase in order of decreasing donicity of the solvent media.
Template-Driven Macrolide Closures.
Rastetter, William H.,Phillion, Dennis P.
, p. 3209 - 3214 (2007/10/02)
Thiol-functionalized crown ethers serve as reagents for macrolide closures.The thioesters derived from these crown ethers and ω-hydroxy carboxylic acids yield macrolides when treated with potassium tert-butoxide.The cyclization reaction proceeds via a templated conformation in which the ω-alkoxide is held proximate to the thioester through ionic bonding to the crown-bound potassium cation.Variations in crown ether structure in the series 1-4 show that the criterion of proximate binding is necessary but not sufficient to ensure efficient macrolide closure.The optimal crown ether reagent is thought to provide transition-state stabilization for the attack of the alkoxide on the thioester carbonyl by situating the carbonyl oxygen immediately adjacent to the crown-bound potassium cation.
