167298-42-2Relevant articles and documents
Serum stability of selected decapeptide agonists of KISS1R using pseudopeptides
Asami, Taiji,Nishizawa, Naoki,Ishibashi, Yoshihiro,Nishibori, Kimiko,Nakayama, Masaharu,Horikoshi, Yasuko,Matsumoto, Shin-Ichi,Yamaguchi, Masashi,Matsumoto, Hirokazu,Tarui, Naoki,Ohtaki, Tetsuya,Kitada, Chieko
, p. 6391 - 6396 (2012/11/07)
Metastin/kisspeptin, a 54-amino acid peptide, is the ligand of the G-protein-coupled receptor KISS1R which plays a key role in pathways that regulate reproduction and cell migration in many endocrine and gonadal tissues. The N-terminally truncated decapep
Antiangiogenic effect of dual/selective α5 β1/αvβ3 integrin antagonists designed on partially modified retro-inverso cyclotetrapeptide mimetics
Gentilucci, Luca,Cardillo, Giuliana,Spampinato, Santi,Tolomelli, Alessandra,Squassabia, Federico,De Marco, Rossella,Bedini, Andrea,Baiula, Monica,Belvisi, Laura,Civera, Monica
body text, p. 106 - 118 (2010/04/24)
Recent evidence highlighted the role of α5β 1 integrin in angiogenesis and in regulating α vβ3 integrin function. As a consequence, selective α5β1 integrin inhibitors or dual α5β1/αvβ3 integrin inhibitors are considered promising candidates for the development of cancer therapeutic agents. In this paper, we describe the synthesis and pharmacological characterization of a minilibrary of cyclotetrapeptide mimetics containing a PMRI Arg-Gly-Asp sequence. In particular, c[(R)- βPheψ(NHCO)Aspψ-(NHCO)Gly-Arg] (3) displayed a good activity in inhibiting the αvβ3 integrin-mediated cell adhesion of fibronectin or vitronectin, as well as the adhesion of fibronectin to the α5β1 integrin. Interestingly, the diastereomeric compound c[(S)-βPheψ(NHCO)Aspψ(NHCO)Gly-Arg] (2) maintained a good efficacy in inhibiting α5β1 integrin while gaining a certain selectivity over αvβ 3 integrin. These two integrin antagonists significantly inhibited bFGF-induced human endothelial cell tube formation at submicromolar concentrations. Conformational analysis and Molecular Docking calculations suggest that the different α5β1 versus αvβ3 selectivity of 2 and 3 can be rationalized on the basis of the alternative display of the aromatic side chain adjacent to Asp.
N-urethane-protected amino alkyl isothiocyanates: Synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides
Sureshbabu, Vommina V.,Naik, Shankar A.,Hemantha,Narendra,Das, Ushati,Guru Row, Tayur N.
supporting information; experimental part, p. 5260 - 5266 (2009/12/06)
(Chemical Equation Presented) Synthetically useful N-Fmoc amino-alkyl isothiocyanates have been described, starting from protected amino acids. These compounds have been synthesized in excellent yields by thiocarbonylation of the monoprotected 1,2-diamines with CS2/TEA/p-TsCl, isolated as stable solids, and completely characterized. The procedure has been extended to the synthesis of amino alkyl isothiocyanates from Boc- and Z-protected amino acids as well. The utility of these isothiocyanates for peptidomimetics synthesis has been demonstrated by employing them in the preparation of a series of dithioureidopeptide esters. Boc-Gly-OH and Boc-Phe-OH derived isothiocyanates 9a and 9c have been obtained as single crystals and their structures solved through X-ray diffraction. They belong to the orthorhombic crystal system, and have a single molecule in the asymmetric unit (Z′ = 1). 9a crystallizes in the centrosymmetric space group Pbca, while 9c crystallizes in the noncentrosymmetric space group P212121.
New pyrrole-based amino acids for the synthesis of peptidomimetic constrained scaffolds
Alongi, Maddalena,Minetto, Giacomo,Taddei, Maurizio
, p. 7069 - 7072 (2007/10/03)
A new family of pyrrole-based amino acids have been prepared through the microwave assisted Paal-Knorr reaction of 1-4 ketoesters derived from the corresponding β-ketoester with a functional homologation. The carboxylic group is located in position 3 of the pyrrole, whereas the amino group, protected with the Cbz moiety, is present on the side chain in positions 1 or 2. These compounds were used to prepare constrained oligopeptides.
A novel, simple, chemoseleetive and practical protocol for the reduction of azides using In/NH4Cl
Reddy, G. Vidyasagar,Rao, G. Venkat,Iyengar
, p. 3937 - 3938 (2007/10/03)
A simple, mild and efficient method for the reduction of azides to amines using In/NH4Cl is described.
2-6-diaminopurine precursors
-
, (2008/06/13)
The present invention relates to compounds of formula (IV): STR1 wherein Ra and Rb each represent a hydrogen atom or together form an alkylidene group.
Modified Amino Acids and Peptides. Part 2. A Convenient Conversion of Amino and Peptide Alcohols into Amines.
Kokotos, George,Constantinou-Kokotou, Violetta
, p. 3117 - 3132 (2007/10/02)
A convenient general method for the conversion of N-protected amino and peptide alcohols into amines is described.The hydroxyl group of the alcohols was replaced by an azido group and a substituted amino group after activation through mesylation.Hydrogenation of the N-protected amino azides afforded optically active monoprotected diamines or free 1,2-diamines depending on the N-protecting group.Selective reduction of the azido group in the presence of a benzyloxycarbonyl group was performed in high yield using sodium borohydride in the presence of 10percent palladium on charcoal.