363622-48-4Relevant academic research and scientific papers
Stafia-1: a STAT5a-Selective Inhibitor Developed via Docking-Based Screening of in Silico O-Phosphorylated Fragments
Natarajan, Kalaiselvi,Müller-Klieser, Daniel,Rubner, Stefan,Berg, Thorsten
, p. 148 - 154 (2020)
We present a new approach for the identification of inhibitors of phosphorylation-dependent protein–protein interaction domains, in which phenolic fragments are adapted by in silico O-phosphorylation before docking-based screening. From a database of 10 369 180 compounds, we identified 85 021 natural product-derived phenolic fragments, which were virtually O-phosphorylated and screened for in silico binding to the STAT3 SH2 domain. Nine screening hits were then synthesized, eight of which showed a degree of in vitro inhibition of STAT3. After analysis of its selectivity profile, the most potent inhibitor was then developed to Stafia-1, the first small molecule shown to preferentially inhibit the STAT family member STAT5a over the close homologue STAT5b. A phosphonate prodrug based on Stafia-1 inhibited STAT5a with selectivity over STAT5b in human leukemia cells, providing the first demonstration of selective in vitro and intracellular inhibition of STAT5a by a small-molecule inhibitor.
Photophysical Properties of Silyl-Substituted Stilbene Derivatives
Maeda, Hajime,Horikoshi, Ryo,Yamaji, Minoru,Furuyama, Taniyuki,Segi, Masahito
supporting information, p. 3410 - 3422 (2020/06/17)
The effects of silyl groups on the structural, absorption, fluorescence, and photoisomerization properties of stilbenes were investigated. In comparison to that of the parent stilbene (1), fluorescence quantum yields (Φf) of Me3Si-substituted stilbenes 2–4 and 6 in solution were higher. Derivative 5, in which Me3Si groups are present at all ortho positions of the arene moieties, did not fluoresce at room temperature. The absorption and fluorescence wavelength maxima of Me3SiMe2Si-substituted stilbene 7 occurred at longer wavelengths compared to those of the Me3Si analog 2. The results of theoretical calculations showed that this difference is a consequence of an increase in the HOMO energy of 7 caused by orbital interaction between π-system and the σ(Si–Si) orbital. Stilbene 14, with two Me3Si-C≡C groups at both para positions, had a high Φf (0.95). The calculated transition dipole moment (μ) was well correlated with Φf. Derivative 21, which contains Ph2N and Me3SiC≡C groups exhibited solvatofluorochromism because it possesses a twisted intramolecular charge transfer (TICT) excited state in which the Ph2N group and the aromatic ring are orthogonal.
Photoinduced energy and electron transfer in phenylethynyl-bridged zinc porphyrin-oligothienylenevinylene-C60 ensembles
Urbani, Maxence,Ohkubo, Kei,Islam, D. M. Shafiqul,Fukuzumi, Shunichi,Langa, Fernando
supporting information; experimental part, p. 7473 - 7485 (2012/07/28)
Donor-bridge-acceptor triad (Por-2TV-C60) and tetrad molecules ((Por)2-2TV-C60), which incorporated C60 and one or two porphyrin molecules that were covalently linked through a phenylethynyl-oligothienylenevinyl
A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: Synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids
Goek, Yaar,Noel, Timothy,Eycken, Johan Van Der
experimental part, p. 2768 - 2774 (2011/03/18)
The synthesis of a novel C2-symmetric bisphosphane ligand was accomplished starting from trans-(2R,3R)-bis(3′,5′-diphenylphenyl) cyclopropane-1,1-dimethanol as a key intermediate. This ligand was tested in the asymmetric rhodium(I)-catalyzed 1,
Synthesis, characterization, and optical response of dipolar and non-dipolar poly(phenylenevinylene) dendrimers
Diez-Barra,Garcia-Martinez,Merino,Del Rey,Rodriguez-Lopez,Sanchez-Verdu,Tejeda
, p. 5664 - 5670 (2007/10/03)
New dipolar and non-dipolar poly(phenylenevinylene) dendrimers bearing electron-donating and electron-withdrawing groups have been efficiently synthesized using Heck and Horner-Wadsworth-Emmons reactions. The photoluminescence of these systems may be tuned in the blue zone by choosing the appropriate peripheral groups. Despite the meta-substitution pattern, large Stokes shifts can be observed when π-donor and π-acceptor groups are connected by a m-phenylenevinylene system.
