936627-97-3Relevant academic research and scientific papers
Development of new catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds via ring opening-asymmetric reclosure of hydroxylactams
Sengoku, Tetsuya,Miyoshi, Ayako,Tsuda, Tamaki,Inuzuka, Toshiyasu,Sakamoto, Masami,Takahashi, Masaki,Yoda, Hidemi
, (2020/05/18)
Catalytic enantioselective formation of methylenelactam-based N,O-spirocyclic compounds is developed. Hydroxylactams prepared from N-carbonyl phthalimides and β-amido functionalized allylboronates underwent ring opening-asymmetric reclosure in the presence of catalytic amounts of MgBr2 and a chiral aminophenol to afford the corresponding N,O-spirocyclic compounds in excellent yields and high enantioselectivities.
Electrostatic repulsion and hydrogen-bonding interactions in a simple N-aryl-L-valinamide organocatalyst control the stereoselectivity in asymmetric aldol reactions
Tanimura, Yuya,Yasunaga, Kenji,Ishimaru, Kaori
supporting information, p. 6535 - 6539 (2013/11/06)
A novel stereocontrol method for asymmetric aldol reactions of aldehydes with ketones is described. The stereoselectivity of the products is controlled by the electrostatic repulsion and hydrogen-bonding interactions of an N-aryl-L-valinamide catalyst. Th
Synthesis and biological evaluation of chiral α-aminoanilides with central antinociceptive activity
Corbo, Filomena,Franchini, Carlo,Lentini, Giovanni,Muraglia, Marilena,Ghelardini, Carla,Matucci, Rosanna,Galeotti, Nicoletta,Vivoli, Elisa,Tortorella, Vincenzo
, p. 1907 - 1915 (2008/02/01)
Tocainide and related optically active chiral α-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.
