86996-83-0Relevant academic research and scientific papers
Designing Structural Motifs for Clickamers: Exploiting the 1,2,3-Triazole Moiety to Generate Conformationally Restricted Molecular Architectures
Zornik, Denise,Meudtner, Robert M.,Ela Malah, Tamer,Thiele, Christina M.,Hecht, Stefan
supporting information; experimental part, p. 1473 - 1484 (2011/04/15)
Noncovalent interactions, especially hydrogen-bonding interactions as well as electrostatic forces, confined within one macromolecule are the key to designing foldamers that adopt well-defined conformations in solution. In the context of significant recent activities in the area of triazole-connected foldamers, so-called clickamers, we present a fundamental study that compares various model compounds that bear adjacent N-, O-, or F-heteroatom substituents. The interplay of attractive and repulsive interactions leads to rotational constraints around the single bonds attached to both the 1- and 4-positions of the 1,2,3-triazole moiety and should therefore be able to induce well-defined conformational preferences in higher oligomers and polymers, that is, foldamers. Various compounds were synthesized and characterized with regard to their preferred conformations in all three aggregation statesa-that is, in the gas phase, in solution as well as in the solid statea-by employing DFT calculations, NMR spectroscopic experiments, and X-ray crystallography, respectively. On the basis of the thus-obtained general understanding of the conformational behavior of the individual connection motifs, heterostructures were prepared from different motifs without affecting their distinct folding characteristics. Therefore, this work provides a kind of foldamer construction kit, which should enable the design of various clickamers with specific shape and incorporated functionality. A foldamer construction kit: Various heterostructures "clicked" together by structure-directing triazole moieties were investigated with regard to their conformational behavior. Different heteroatoms (X; see graphic) can be used to bias the conformation around the N(1)- and C(4)-connecting single bonds of the triazoles based on tunable noncovalent interactions.
Synthesis and biological evaluation of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives as PTP1B inhibitors
Tong, Yuan Feng,Zhang, Pei,Chen, Feng,Hao, Ling Hua,Ye, Fei,Tian, Jin Ying,Wu, Song
scheme or table, p. 1415 - 1418 (2011/10/09)
Based on the fact that petroselinic acid showed good inhibitory activity (IC50=6.99μmol/L) against protein tyrosine phophatase 1B(PTP1B) in vitro, a series of novel N-(alkoxyphenyl)-aminocarbonylbenzoic acid derivatives were designed and synthesized. The results indicated that most of the derivatives showed more potent activities against PTP1B. Especially, compound 13 had obvious activity with an IC50 of 106nmol/L in vitro.
Modulating large-area self-assembly at the solid-liquid interface by pH-mediated conformational switching
Piot, Luc,Meudtner, Robert M.,Malah, Tamer El,Hecht, Stefan,Samori, Paolo
supporting information; experimental part, p. 4788 - 4792 (2009/12/05)
The two-dimensional ordering of molecules adsorbed on surfaces at the solid-liquid interface that are capable to undergo large conformational changes upon the application of an external chemical stimulus was investigated. Large-area self-assembly at the solid-liquid interface was modulated using pH-mediated conformational switching. Scanning tunneling microscopy (STM) visualization was attempted for the first time to examine and visualize large conformational changes of a responsive molecular building block resulting in its altered self-assemble behavior at the solid-liquid interface. It was observed that protonation can work effectively to overcome the repulsive interaction between certain 2,6-bis (1-aryl-1,2,3-triazol-4-yl) pyridine (BTP) molecules and also in the formation of an extended conformation on a HOPG surface. The method has encouraged the efforts towards development of reversible pH triggered switches at the solid-liquid interface.
