18453-32-2Relevant articles and documents
Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance
Cheng, Bao,Zhu, Guirong,Meng, Linghua,Wu, Guolin,Chen, Qin,Ma, Shengming
supporting information, (2021/11/22)
Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsymmetric biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogues were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR.
Effect of a Pendant Acceptor on Thermally Activated Delayed Fluorescence Properties of Conjugated Polymers with Backbone-Donor/Pendant-Acceptor Architecture
Yang, Yike,Li, Kuofei,Wang, Chenxu,Zhan, Hongmei,Cheng, Yanxiang
supporting information, p. 574 - 581 (2019/02/05)
Three sets of conjugated polymers with backbone-donor/pendant-acceptor architectures, named PCzA3PyB, PCzAB2Py, and PCzAB3Py, are designed and synthesized. The three isomeric benzoylpyridine-based pendant acceptor groups are 6-benzoylpyridin-3-yl (3PyB), 4-((pyridin-2-yl)carbonyl)phenyl (B2Py) and 4-((pyridin-3-yl)carbonyl)phenyl (B3Py), whereas the identical backbone consists of 3,6-carbazolyl and 2,7-acridinyl rings. One acridine ring and each acceptor group constitute a definite thermally activated delayed fluorescence (TADF) unit, incorporated into the main chain of the polymers through the 2,7-position of the acridine ring with the varied content. All of the polymers display legible TADF features with a short microsecond-scale delayed lifetime (0.56–1.62 μs) and a small singlet/triplet energy gap (0.10–0.19 eV). Progressively redshifted emissions are observed in the order PCzAB3Py, PCzA3PyB, and PCzAB2Py owing to the different substitution patterns of the pyridyl group. Photoluminescence quantum yields can be improved by regulating the molar content of the TADF unit in the range 0.5–50 %. The non-doped organic light-emitting devices (OLEDs) fabricated by solution-processing technology emit yellow-green to orange light. The polymers with 5 mol % of the TADF unit exhibit excellent comprehensive electroluminescence performance, in which PCzAB2Py5 achieves a maximum external quantum efficiency (EQE) of 11.9 %, low turn-on voltage of 3.0 V, yellow emission with a wavelength of 573 nm and slow roll-off with EQE of 11.6 % at a luminance of 1000 cd m?2 and driving voltage of 5.5 V.
Pyridine-directed asymmetric hydrogenation of 1 1-diarylalkenes
Yang, Hailong,Wang, Erfei,Yang, Ping,Lv, Hui,Zhang, Xumu
supporting information, p. 5062 - 5065 (2017/11/07)
Highly enantioselective pyridine-directed rhodium-catalyzed asymmetric hydrogenation of challenging 1 1-diarylalkenes is achieved by using [Rh(NBD)DuanPhos]BF4 as a precatalyst. Various types of 2-pyridine substituted 1 1-diarylalkenes could be hydrogenated with good to excellent enantioselectivities which provide an efficient route to the synthesis of pharmaceutically and biologically active compounds containing a 2-pyridyl ethane unit.