88831-04-3Relevant academic research and scientific papers
Efficient synthesis of peptides by extension at the N- and C-terminii of arginine
Katritzky, Alan R.,Meher, Geeta,Narindoshvili, Tamari
experimental part, p. 7153 - 7158 (2009/05/07)
(Chemical Equation Presented) L-Nω-Nitroarginine and L-arginine were coupled with N-(Cbz-α-aminoacyl)benzotriazoles and N-Cbz-dipeptidoylbenzotriazoles to provide arginine LL-dipeptides 9a-e, 11a-d; LLL-tripeptides 18a-c, 20; and diastereomeric mixtures (9b+9b′), (9c+9c′), (11b+11b′) and (18c+18c′) [compound numbers written within parentheses represent a diastereomeric mixture or racemate; compound numbers without parentheses represent an achiral compound or a single enantiomer] by extension at the N-terminus of arginine, in isolated yields of 66-95% with complete retention of chirality as evidenced by NMR and HPLC analysis. Arginine LL-dipeptides 15a-d were synthesized by extension at the C-terminus of arginine in isolated yield of 66-80%, using benzotriazole activated arginine L-ωNO2-Arg-Bt, 13. Our methodology has also been used to synthesize the protected RGD peptide (Cbz α-L-ωNO2-Arg-Gly-L-Asp-(OH) 2) 21.
Tryptophan-containing dipeptide derivatives as potent PPARγ antagonists: Design, synthesis, biological evaluation, and molecular modeling
Deng, Guanghui,Liu, Zhiguo,Ye, Fei,Luo, Xiaomin,Zhu, Weiliang,Shen, Xu,Liu, Hong,Jiang, Hualiang
experimental part, p. 2699 - 2716 (2009/04/11)
The discovery of peroxisome proliferator-activated receptor γ (PPARγ) antagonists (also termed "selective PPARγ modulators, SPPARγM") is now of a great interest in the treatment of diabetes and obesity. The structure of compound 1a (G3335, Fig. 1), a novel class of PPARγ antagonist, is entirely different from that of other reported PPARγ antagonists. A series of 35 novel analogues (1b-l, 9a-d, 13a-t) were designed, synthesized and evaluated against the agonistic effects exerted by rosiglitazone. These results indicated that most functional groups of 1a were conserved, and six new compounds (1b, 1c, and 9a-d) exhibited strong PPARγ antagonistic activities (IC50 values of 5.2-25.8 μM) against 10 μM rosiglitazone in the promotion of the PPARγ-LBD-CBP (ligand-binding domain and cAMP-response-element binding protein) interaction as investigated by yeast two-hybrid technology based assay. Molecular modeling studies for compounds 1a-d, 1h, 9c-d, and 13a were also presented.
