108957-20-6Relevant articles and documents
Development of Macrocyclic Peptides Containing Epoxyketone with Oral Availability as Proteasome Inhibitors
Li, Daqiang,Zhang, Xiaotuan,Ma, Xiaodong,Xu, Lei,Yu, Jianjun,Gao, Lixin,Hu, Xiaobei,Zhang, Jiankang,Dong, Xiaowu,Li, Jia,Liu, Tao,Zhou, Yubo,Hu, Yongzhou
, p. 9177 - 9204 (2018/10/24)
Macrocyclization has been frequently utilized for optimizing peptide or peptidomimetic-based compounds. In an attempt to obtain potent, metabolically stable, and orally available proteasome inhibitors, 30 oprozomib-derived macrocyclic peptides with structural diversity in their N-terminus and linker were successively designed and synthesized for structure-activity relationship (SAR) studies. As a consequence, the macrocyclic peptides with N-methyl-pyrazole (24p, 24x), imidazole (24t), and pyrazole (24v) as their respective N-termini exhibited favorable in vitro activity and metabolic stability, which translated into their potent in vivo proteasome inhibitory activity after oral administration. In particular, compound 24v, as the most distinguished one among this series, displayed excellent chymotrypsin-like (ChT-L, β5) inhibitory potency (IC50 = 16 nM), low nanomolar antiproliferative activity against all three of the tested cell lines, and superior metabolic stability in mouse liver microsome (MLM), as well as favorable inhibition against ChT-L compared to that of oprozomib in BABL/c mice following po administration at a comparatively low dose, thereby representing a promising candidate for further development.
Efficient synthesis of benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-ω- iodoalkanoates
Koseki, Yohei,Yamada, Haruka,Usuki, Toyonobu
, p. 580 - 586 (2011/06/21)
The efficient synthesis of four benzyl 2-(S)-[(tert-butoxycarbonyl)amino]- ω-iodoalkanoates {benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-3- iodopropanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-4-iodobutanoate, benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-
Synthesis of new peptide nucleic acid monomer with glycylglycine backbone
Yamasaki, Tetsuo,Abdel-Aziz, Mohamed,Iwashita, Takashi,Watanabe, Akiko,Sakamoto, Masanori,Otsuka, Masami
, p. 1111 - 1113 (2007/10/03)
New thymine peptide nucleic acid (PNA) monomer with glycylglycine backbone was prepared. This involved a key step of the coupling between iodinated serine (3) and 3-benzoylthymine.
Synthesis of L-selenocystine, L-[77Se]selenocystine and L-tellurocystine
Stocking, Emily M.,Schwarz, Jessie N.,Senn, Hans,Salzmann, Michael,Silks, Louis A.
, p. 2443 - 2447 (2007/10/03)
Synthetic routes for the synthesis of stable isotope labelled amino acids which contain either a selenium or a tellurium atom have been explored. L-Selenocystine, L-[77Se]selenocystine and L-tellurocystine have been constructed in four steps from commercially available methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionate. The sequence of reactions has been successfully scaled up giving significant quantities of the chalcogen based amino acids in fair to good overall yield. Copyright 1997 by the Royal Society of Chemistry.
Synthesis of all Three Regioisomers of Pyridylalanine
Walker, Michael A.,Kaplita, Khane Pham,Chen, Ti,King, H. Dalton
, p. 169 - 170 (2007/10/03)
Pyridylalanines 4-6, differing from one another by the position of attachment on the heterocyclic ring were synthesized in moderate yield starting from serine and 2-, 3- and 4-bromopyridine respectively.
Enantioselective synthesis of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine; agents suitable for the solid-phase synthesis of peptides containing nonhydrolyzable analogues of O-phosphotyrosine
Smyth,Burke Jr.
, p. 551 - 554 (2007/10/02)
Enantioselective convergent syntheses of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine are reported.
Preparation of Enantiomerically Pure Protected 4-Oxo-α-amino Acids and 3-Aryl-α-amino Acids from Serine
Jackson, Richard F. W.,Wishart, Neil,Wood, Anthony,James, Keith,Wythes, Martin J.
, p. 3397 - 3404 (2007/10/02)
The organozinc reagent 13, prepared from the protected β-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-α-amino acids 17 in 39-90percent yield (13 examples).Zinc reagent 13 can also be coupled with aryl iodides in the presence of bis(tri-o-tolylphosphine)palladium dichloride to give enantiomerically pure protected phenylalanine analogues 26, 29, and 30 in 10-67percent yield (11 examples).The reaction tolerates the presence of a variety of functional groups in the acid chloride and the aryl iodide and provides derivatives which can be easily deprotected, at either the carboxyl or amino terminus, to give intermediates suitable for peptide synthesis.
