327048-63-5Relevant articles and documents
Amide bond formation with a new fluorous carbodiimide: Separation by reverse fluorous solid-phase extraction
Del Pozo, Carlos,Keller, Adam I.,Nagashima, Tadamichi,Curran, Dennis P.
, p. 4167 - 4170 (2007)
A new fluorous carbodiimide is introduced along with a convenient procedure for amide coupling reactions. Reactions of acids and amines under standard conditions for carbodiimide couplings, followed by simple reverse fluorous solid-phase extraction (FSPE) over standard silica gel, provide the target amide products in good yields and purities. The use of HFE-7100 as a fluorous solvent is crucial for the success of the reverse FSPE.
Design, synthesis, and biological evaluation of new diaminoquinazolines as β-catenin/Tcf4 pathway inhibitors
Mao, Yongjun,Lin, Nan,Tian, Wang,Han, Xiaofeng,Han, Xiaobing,Huang, Ziwei,An, Jing
experimental part, p. 1346 - 1359 (2012/04/04)
More than 50 new diaminoquinazoline derivatives have been synthesized and evaluated in a colon carcinoma cell growth inhibition assay using HCT116 and SW480 cells. Twenty compounds with good cell growth inhibitory activities (50 values 50 values of 1.5-2.5 μM for HCT116 cells with the luciferase reporter assay.
Design, synthesis, and modeling of novel cyclic thrombin receptor-derived peptide analogues of the Ser42-Phe-Leu-Leu-Arg46 motif sequence with fixed conformations of pharmacophoric groups: Importance of a Phe/Arg/NH2 cluster for receptor activation and implications in the design of nonpeptide thrombin receptor mimetics
Alexopoulos,Panagiotopoulos,Mavromoustakos,Fatseas,Paredes-Carbajal,Mascher,Mihailescu,Matsoukas
, p. 328 - 339 (2007/10/03)
The novel cyclic analogues cyclo(Phe-Leu-Leu-Arg-εLys-Dap) (1) and cyclo(D-Phe-Leu-Leu-ArgεLys-Dap) (2), which differ only in the absolute conformation of Phe, have been designed and synthesized based upon the minimal peptide sequence Phe-Leu-Leu-Arg which has been found to exhibit biological activity for the thrombin receptor. Compound 1, in which all amino acids have the L-configuration, exhibited higher activity in the rat aorta relaxation and rat longitudinal muscle bioassays compared to compound 2, in which the Phe residue is in the D-configuration. This is attributed to the spatial proximity of the Phe and Arg in compound 1 which does not exist in its diastereomeric compound 2, as is depicted from a combination of NMR studies and computational analysis. Structure - activity studies (SAR) showed that the Phe and Arg side chains along with a primary amino group form an active recognition motif that is augmented by the presence of a second primary amino group in the cyclic peptide. We suggest that a comparable cyclic conformation may be responsible for the interaction of linear TRAPs with the thrombin receptor. The validity of this proposition was tested by the synthesis of four active nonpeptide thrombin receptor mimetics. Substance (S)-N-(6-guanidohexanoyl)-N′-(2-amino-3-phenylpropionyl)piperazine (3), in which the pharmacophoric phenyl, guanidino, and amino groups were incorporated onto a piperazine template, was found to be the most active compared to the other synthesized compounds which lack the amino pharmacophoric group.
