83529-46-8Relevant academic research and scientific papers
Synthesis and optimization of novel α-phenylglycinamides as selective TRPM8 antagonists
Kobayashi, Jun-ichi,Hirasawa, Hideaki,Ozawa, Tetsuji,Ozawa, Tomonaga,Takeda, Hiroo,Fujimori, Yoshikazu,Nakanishi, Osamu,Kamada, Noboru,Ikeda, Tetsuya
, p. S1 - S51 (2016/12/30)
Transient receptor potential melastatin 8 (TRPM8) is activated by innocuous cold and chemical substances, and antagonists of this channel have been considered to be effective for pain and urinary diseases. N-(3-aminopropyl)-2-{[(3-methylphenyl)methyl]oxy}-N-(2-thienylmethyl)benzamide hydrochloride (AMTB), a TRPM8 antagonist, was proposed to be effective for overactive bladder and painful bladder syndrome; however, there is a potential risk of low blood pressure. We report herein the synthesis and structure–activity relationships of novel phenylglycine derivatives that led to the identification of KPR-2579 (20l), a TRPM8 selective antagonist. KPR-2579 reduced the number of icilin-induced wet-dog shakes and rhythmic bladder contraction in rats, with no negative cardiovascular effects at the effective dose.
Rh-catalyzed asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution
Fan, Dongyang,Lu, Jian,Liu, Yang,Zhang, Zhenfeng,Liu, Yangang,Zhang, Wanbin
, p. 5541 - 5547 (2016/08/05)
Catalyzed by a rhodium complex of P-stereogenic diphosphine ligand trichickenfootphos (TCFP), asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution has been realized for the preparation of chiral arylglycines with good yields and enantioselectivities.
Derecemization par protonation enantioselective. Application a un α-aminoacide, la phenylglycine
Duhamel, Lucette,Plaquevent, Jean-Christophe
, p. 75 - 83 (2007/10/02)
This work describes the application of deracemization by enantioselective protonation to α-aminoacid derivatives.Esters of phenylglycine are readly converted into Schiff bases.Melanation of the latter by a lithium amide, followed by protonation by a chiral acid, leads to the optically active starting materials (e.e. as high as 70percent).Chiral acids can easily be retrieved after protonation with excellent yields and conservation of enantiomeric purity.A mechanism responsible for the asymmetric induction is suggested by means of a study of the parameters modifying the selectivity, such as the nature of protecting groups, chiral acid, and lithium amide.
