66866-45-3Relevant articles and documents
Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists
Kambe, Tohru,Maruyama, Toru,Nagase, Toshihiko,Ogawa, Seiji,Minamoto, Chiaki,Sakata, Kiyoto,Maruyama, Takayuki,Nakai, Hisao,Toda, Masaaki
experimental part, p. 702 - 713 (2012/03/11)
To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified γ-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the γ-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented.
Design and synthesis of α-ketoamides as cathepsin s inhibitors with potential applications against tumor invasion and angiogenesis
Chen, Jo-Chun,Uang, Biing-Jiun,Lyu, Ping-Chiang,Chang, Jang-Yang,Liu, Ko-Jiunn,Kuo, Ching-Chuan,Hsieh, Hsing-Pang,Wang, Hsin-Chieh,Cheng, Chao-Sheng,Chang, Yi-Hsun,Chang, Margaret Dah-Tsyr,Chang, Wun-Shaing Wayne,Lin, Chun-Cheng
scheme or table, p. 4545 - 4549 (2010/08/19)
A series of small molecules bearing an α-ketoamide warhead were synthesized and evaluated for their ability to inhibit cathepsin S, a key proteolytic enzyme upregulated in many cancers during tumor progression and metastasis. Most of the synthetic compounds were noncytotoxic, but several robustly inhibited cathepsin S (IC50 10 nM) and potently suppressed cell migration, invasion, and capillary tube formation. These results highlight the potential of α-ketoamide therapy for preventing or delaying cancer spread.
Building functionalized peptidomimetics: Use of electroauxiliaries for introducing N-acyliminium ions into peptides
Sun, Haizhou,Martin, Connor,Kesselring, David,Keller, Rebecca,Moeller, Kevin D.
, p. 13761 - 13771 (2007/10/03)
A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.
