17719-79-8Relevant articles and documents
Sequence-defined polymers via orthogonal allyl acrylamide building blocks
Porel, Mintu,Alabi, Christopher A.
supporting information, p. 13162 - 13165 (2015/03/30)
Biological systems have long recognized the importance of macromolecular diversity and have evolved efficient processes for the rapid synthesis of sequence-defined biopolymers. However, achieving sequence control via synthetic methods has proven to be a difficult challenge. Herein we describe efforts to circumvent this difficulty via the use of orthogonal allyl acrylamide building blocks and a liquid-phase fluorous support for the de novo design and synthesis of sequence-specific polymers. We demonstrate proof-of-concept via synthesis and characterization of two sequence-isomeric 10-mer polymers. 1H NMR and LCMS were used to confirm their chemical structure while tandem MS was used to confirm sequence identity. Further validation of this methodology was provided via the successful synthesis of a sequence-specific 16-mer polymer incorporating nine different monomers. This strategy thus shows promise as an efficient approach for the assembly of sequence-specific functional polymers.
Deconstructing 14-phenylpropyloxymetopon: Minimal requirements for binding to mu opioid receptors
Stavitskaya, Lidiya,Shim, Jihyun,Healy, Jason R.,Matsumoto, Rae R.,MacKerell Jr., Alexander D.,Coop, Andrew
experimental part, p. 4556 - 4563 (2012/09/07)
A series of phenylpropyloxyethylamines and cinnamyloxyethylamines were synthesized as deconstructed analogs of 14-phenylpropyloxymetopon and analyzed for opioid receptor binding affinity. Using the Conformationally Sampled Pharmacophore modeling approach, we discovered a series of compounds lacking a tyrosine mimetic, historically considered essential for μ opioid binding. Based on the binding studies, we have identified the optimal analogs to be N-methyl-N-phenylpropyl-2-(3-phenylpropoxy)ethanamine, with 1520 nM, and 2-(cinnamyloxy)-N-methyl-N-phenethylethanamine with 1680 nM affinity for the μ opioid receptor. These partial opioid structure analogs will serve as the novel lead compounds for future optimization studies.
Ruthenium porphyrin catalyzed tandem sulfonium/ammonium ylide formation and [2,3]-sigmatropic rearrangement. A concise synthesis of (±)-platynecine
Zhou, Cong-Ying,Yu, Wing-Yiu,Chan, Philip Wai Hong,Che, Chi-Ming
, p. 7072 - 7082 (2007/10/03)
meso-Tetrakis(p-tolyl)porphyrinatoruthenium(II) carbonyl, [Ru II(TTP)(CO)], can effect intermolecular sulfonium and ammonium ylide formation by catalytic decomposition of diazo compounds such as ethyl diazoacetate (EDA) in the presence of allyl sulfides and amines. Exclusive formation of [2,3]-sigmatropic rearrangement products (70-80% yields) was observed without [1,2]-rearrangement products being detected. The Ru-catalyzed reaction of EDA with disubstituted allyl sulfides such as crotyl sulfide produced an equimolar mixture of anti- and syn-2-(ethylthio)-3-methyl-4- pentenoic acid ethyl ester. The analogous "EDA + N,N- dimethylcrotylamine" reaction afforded a mixture of anti- and syn-2-(N,N-dimethylamino)-3-methyl-4-pentenoic acid ethyl esters with a diastereoselectivity of 3:1. The observed catalytic activity of [Ru II(TTP)(CO)] for the ylide [2,3]-sigmatropic rearrangement is comparable to the reported examples involving [Rh2(CH 3CO2)4] and [Cu(acac)2] as catalyst. Similarly, cyclic sulfonium and ammonium ylides can be produced by intramolecular reaction of a diazo group tethered to allyl sulfides and amines under the [RuII-(TTP)(CO)]-catalyzed reaction conditions. The subsequent [2,3]-sigmatropic rearrangement of the cyclic ylides furnished 2-allyl-substituted sulfur and nitrogen heterocycles in good yields (>90%). By employing [RuII(TTP)(CO)] as catalyst, the cyclic ammonium ylide [2,3]-sigmatropic rearrangement reaction was successfully applied for the total synthesis of (±)-platynecine starting from cis-2-butenediol.
Electrochemical reductive allylation of N-benzylideneethanolamine
Nawaz Khan,Jayakumar,Pillai
, p. 6807 - 6809 (2007/10/03)
Electrochemical reductive allylation of N-benzylideneethanolamine by allyl bromide mediated by a Pb(II)/Pb(0) redox couple is reported.
SYNTHESE DES MORPHOLINES. II. ALLYLATION CHIMIOSELECTIVE DES 2-AMINOALCOOLS, PRODUITS DE DEPART POUR LA FORMATION DES MORPHOLINES.
Dobrev, Alexandre,Spasov, Stefan,Lattes, Armand
, p. 1601 - 1619 (2007/10/02)
La reaction d'allylation des 2-aminoalcools est une reaction chimioselective donnant un acces facile et avec des bons rendements aux alcools correspondants exclusivement N-allyles.Leurs structures ont ete prouvees par spectrometrie de masse, IR et 1H RMN.
