123731-68-0Relevant articles and documents
Long-range stereo-relay: Relative and absolute configuration of 1,n-glycols from circular dichroism of liposomal porphyrin esters
MacMillan, John B.,Molinski, Tadeusz F.
, p. 9944 - 9945 (2004)
The relative and absolute configurations of long-chain syn- and anti-1,5-, 1,7- and 1,9-glycols were determined from exciton-coupled circular dichroism (ECCD) of the corresponding bis-5-(4′-carboxyl)-5,10,15,20-tetraphenylporphyrin esters measured in uniform (φ = 26 nm), unilamellar liposomes. Long-range transmission of configuration by ECCD is made possible through partial ordering of glycol ester-lipid molecules by liposomal bilayers. Copyright
A formal synthesis of porantheridine and an epimer
Bates, Roderick W.,Lu, Yongna
, p. 9460 - 9465 (2009)
(Chemical Equation Presented) A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.
Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β2-adrenergic receptor
Plazinska, Anita,Pajak, Karolina,Rutkowska, Ewelina,Jimenez, Lucita,Kozocas, Joseph,Koolpe, Gary,Tanga, Mary,Toll, Lawrence,Wainer, Irving W.,Jozwiak, Krzysztof
, p. 234 - 246 (2014/01/17)
The β2-adrenergic receptor (β2-AR) agonist [3H]-(R,R′)-methoxyfenoterol was employed as the marker ligand in displacement studies measuring the binding affinities (Ki values) of the stereoisomers of a series of 4′-methoxyfenoterol analogs in which the length of the alkyl substituent at α′ position was varied from 0 to 3 carbon atoms. The binding affinities of the compounds were additionally determined using the inverse agonist [3H]-CGP-12177 as the marker ligand and the ability of the compounds to stimulate cAMP accumulation, measured as EC50 values, were determined in HEK293 cells expressing the β2-AR. The data indicate that the highest binding affinities and functional activities were produced by methyl and ethyl substituents at the α′ position. The results also indicate that the Ki values obtained using [3H]-(R,R′)-methoxyfenoterol as the marker ligand modeled the EC50 values obtained from cAMP stimulation better than the data obtained using [3H]-CGP-12177 as the marker ligand. The data from this study was combined with data from previous studies and processed using the Comparative Molecular Field Analysis approach to produce a CoMFA model reflecting the binding to the β2-AR conformation probed by [3H]-(R,R′)-4′-methoxyfenoterol. The CoMFA model of the agonist-stabilized β2-AR suggests that the binding of the fenoterol analogs to an agonist-stabilized conformation of the β2-AR is governed to a greater extend by steric effects than binding to the [3H]-CGP-12177-stabilized conformation(s) in which electrostatic interactions play a more predominate role.
Total synthesis of neopeltolide and analogs
Cui, Yubo,Tu, Wangyang,Floreancig, Paul E.
scheme or table, p. 4867 - 4873 (2010/08/06)
Neopeltolide, a potent cytotoxin from a Carribean sponge, was synthesized through a brief sequence that highlights the use of ethers as oxocarbenium ion precursors. Other key steps include an acid-mediated etherification and sequence that features a Sonogashira reaction, an intramolecular alkyne hydrosilylation reaction, and a Tamao oxidation. The alkene that is required for the oxidative cyclization can be hydrogenated to provide access to the natural product or an epimer, or can be epoxidized or dihydroxylated to form polar analogs.
