13278-39-2Relevant articles and documents
Effect of the substituent position on the electrochemical, optical and structural properties of donor-acceptor type acridone derivatives
Kulszewicz-Bajer, Irena,Zagorska, Malgorzata,Banasiewicz, Marzena,Guńka, Piotr A.,Toman, Petr,Kozankiewicz, Boleslaw,Wiosna-Salyga, Gabriela,Pron, Adam
, p. 8522 - 8534 (2020)
Three new donor-acceptor (D-A) compounds, positional isomers of phenoxazine-substituted acridone, namely 1-phenoxazine-N-hexylacridone ( o-A ), 2-phenoxazine-N-hexylacridone ( m-A ) and 3-phenoxazine-N-hexylacridone ( p-A ), were synthesized. The synthesized compounds showed interesting, isomerism-dependent electrochemistry. Their oxidation was reversible and their potential (givenvs.Fc/Fc+) changed from 0.21 V for o-A to 0.36 V for p-A . In contrast, their reduction was irreversible, isomerism-independent and occurred at rather low potentials (ca.?2.25 to ?2.28 V). The electrochemical results led to the following values of the ionization potentials (IPs) and electron affinities (EAs): 5.03 eV and ?2.14 eV, 5.15 eV and ?2.20 eV, and 5.20 eV and ?2.28 eV for o-A m-A and p-A , respectively. The experimentally obtained values were in very good agreement with those predicted by DFT calculations. All three isomers readily formed single crystals suitable for their structure determination. o-A and p-A crystallized inP1? andP21/nspace groups, respectively, with one molecule per asymmetric unit, while m-A crystallized in theP21/cspace group with two molecules in the asymmetric unit accompanied by disordered solvent molecules. The UV-vis spectra of the studied compounds were isomerism and solvent independent, yielding absorption maxima in the vicinity of 400 nm. Their photoluminescence spectra, in turn, strongly depended on isomerism and the used solvent showing smaller Stokes shifts for the emission bands registered in toluene as compared to the corresponding bands measured in dichloromethane. The photoluminescence quantum yields (?) were systematically higher for toluene solutions reaching the highest value of 20% for p-A . For all three isomers studied, stationary and time-resolved spectroscopic investigations carried out in toluene at different temperatures revealed spectral features indicating a contribution of thermally activated delayed fluorescence (TADF) to the observed spectroscopic behaviour. The measured photoluminescence quantum yields (?) were higher for solid state films of pure compounds and for their dispersions in solid matrices (zeonex) than those recorded for toluene and dichloromethane solutions of the studied phenoxazine-N-hexylacridone isomers. The obtained experimental spectroscopic and structural data were confronted with theoretical predictions based on DFT calculations.
Design, synthesis and bioactivity evaluation of novel N-phenyl-substituted evodiamine derivatives as potent anti-tumor agents
Hao, Xiangyong,Deng, Jiedan,Zhang, Honghua,Liang, Ziyi,Lei, Fang,Wang, Yuqing,Yang, Xiaoyan,Wang, Zhen
, (2022/01/10)
Natural products are important sources for the development of therapeutic medicine, among which evodia fruit has a wide range of medicinal properties in traditional Chinese medicine. Evodiamine, the main active component of evodia fruit, has various anti-cancer effects and has been proved to be a Topo inhibitor. From our previous attempts of modifying evodiamine, we found that the N14 phenyl substituted derivatives had showed great anti-tumor activity, which prompted us to further explore the novel structures and activities of these compounds. Compound 6f, as a N14 3-fluorinated phenyl substituted evodiamine derivative, showed a certain inhibitory activity against Topo I at 200 μM. By studying its anti-tumor effects in vitro, compound 6f could inhibit proliferation and induce apoptosis, as well as arrest the cell cycle of HGC-27 and HT-29 cell lines at G2/M phase in a concentration-dependent manner. Moreover, compound 6f could inhibit the migration and invasion of HGC-27 cell lines. Meanwhile, compound 6f could induce apoptosis of HGC-27 cells by inhibiting PI3K/AKT pathway. Overall, this work demonstrated that the N14 phenyl-substituted evodiamine derivatives had a good inhibitory effect on tumor cells in vitro, providing a promising strategy for developing potential anticancer agents for the treatment of gastrointestinal tumors.
Novel organic compound and organic electroluminescent device comprising novel organic compound
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Paragraph 0076; 0077; 0081; 0082, (2019/07/11)
The invention provides an organic compound represented by a following chemical formula A, wherein R to R, L, Ar, Ar, X, m, n and k are defined as in the protection scope of the invention.
