114444-89-2Relevant academic research and scientific papers
A new metabotropic glutamate receptor agonist with in vivo anti-allodynic activity
Stanley, Nathan J.,Hutchinson, Mark R.,Kvist, Trine,Nielsen, Birgitte,Mathiesen, Jesper Mosolff,Br?uner-Osborne, Hans,Avery, Thomas D.,Tiekink, Edward R.T.,Pedersen, Daniel Sejer,Irvine, Rodney J.,Abell, Andrew D.,Taylor, Dennis K.
, p. 6089 - 6098 (2010)
As part of the vital search towards improved therapeutic agents for the treatment of neuropathic pain, the central nervous system glutamate receptors have become a major focus of research. Outlined herein are the syntheses of two new biologically active 3′-cycloalkyl-substituted carboxycyclopropylglycines, utilizing novel synthetic chemistry. The reaction between substituted 1,2-dioxines and an aminophosphonate furnished the cyclopropane core in a single step with all required stereochemistry of pendant groups. In vitro binding assays at metabotropic glutamate receptors revealed selective activity. In vivo testing in a rodent model of neuropathic pain indicated one amino acid significantly and dose-dependently decreased mechanical allodynia.
A hydrate salt-promoted reductive coupling reaction of nitrodienes with unactivated alkenes
Zhang, Mengmeng,Yang, Liming,Tian, Chao,Zhou, Meng,An, Guanghui,Li, Guangming
, p. 2258 - 2264 (2019)
Transition metal-catalyzed reductive coupling has emerged as a powerful method for the construction of C-C bonds. Herein, a crystalline hydrate, Na2HPO4·7H2O, has been disclosed as an effective promoter for the reductive c
A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines
Dong, De-Jun,Li, Hai-Hua,Tian, Shi-Kai
supporting information; experimental part, p. 5018 - 5020 (2010/06/13)
The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.
Stereoselective E and Z Olefin Formation by Wittig Olefination of Aldehydes with Allylic Phosphorus Ylides. Stereochemistry
Tamura, Rui,Saegusa, Koji,Kakihana, Masato,Oda, Daihei
, p. 2723 - 2728 (2007/10/02)
Sterically crowded allylic tributylphosphorus ylides such as β-γ-disubstituted allylic ylides react with various aldehydes to afford E olefins with high stereoselectivity (E>92percent).As the steric demand of the ylides was decreased, bulky aldehydes were required to achieve high E selectivity.On the other hand, predominant or exclusive formation of Z olefins was achieved by using allylic triphenylphosphorus ylides and tertiary aldehydes like pivaldehyde, while the combination of allylic triphenylphosphorus ylides and such large secondary aldehydes as cyclohexanecarboxaldehyde led to E olefin formation under the lithium salt free conditions.The distinct lithium salt effect was observed in the reaction effected with triphenylphosphorus ylides.The origin of the observed E or Z selectivity can be reasonably explained according to Vedejs' rationale on the Wittig reaction stereochemistry.
