184968-92-1Relevant academic research and scientific papers
C-2 (E)-4-(Styryl)aniline substituted diphenylpyrimidine derivatives (Sty-DPPYs) as specific kinase inhibitors targeting clinical resistance related EGFRT790M mutant
Song, Anran,Zhang, Jianbin,Ge, Yang,Wang, Changyuan,Meng, Qiang,Tang, Zeyao,Peng, Jinyong,Liu, Kexin,Li, Yanxia,Ma, Xiaodong
, p. 2724 - 2729 (2017/04/17)
With the aim to overcome the drug resistance induced by the EGFR T790M mutation (EGFRT790M), herein, a family of diphenylpyrimidine derivatives (Sty-DPPYs) bearing a C-2 (E)-4-(styryl)aniline functionality were designed and synthesized as potential EGFRT790M inhibitors. Among them, the compound 10e displayed strong potency against the EGFRT790M enzyme, with the IC50 of 11.0?nM. Compound 10e also showed a higher SI value (SI?=?49.0) than rociletinib (SI?=?21.4), indicating its less side effect. In addition, compound 10e could effectively inhibit the proliferation of H1975 cells harboring the EGFRT790M mutation, within the concentration of 2.91?μM. Significantly, compound 10e has low toxicity against the normal HBE cell (IC50?=?22.48?μM). This work provided new insights into the discovery of potent and selective inhibitor against EGFRT790M over wild-type (EGFRWT).
Synthesis, Structures and Topochemistry of 2-Monovinyl-Substituted 1,4-Benzoquinones
Irngartinger, Hermann,Stadler, Birgit
, p. 605 - 626 (2007/10/03)
In the course of topochemical investigations of substituted quinones the 2-monovinyl-substituted 1,4-benzoquinones 1 were synthesized by electrochemical oxidation of the corresponding 1,4-dimethoxybenzene derivatives 3 to the quinone bisketals 4 and subsequent hydrolysis. In solution, the aryl-substituted vinylquinones 1a-1t underwent unexpected Diels-Alder additions. The stereochemically unique course of the reaction was proved spectroscopically and by X-ray structure analysis of the dimer 8k. As a basic requirement for the topochemical studies, the crystal structures of eight quinones 1 were determined by X-ray diffraction. In the crystals of 1a, 1c, 1e, 1f, 1i and 1n with an α-type packing arrangement, the vinylic double bonds have short contacts (1 symmetry were formed whereas the dimers 9k and 9t have Cs symmetry. The structures of the cyclobutanes were determined by spectroscopical investigations and in the case of 9b, 9e and 9r additionally by X-ray analysis. Despite short contacts, crystals of 1f and 1i were photostable. This is probably because of insufficient lattice flexibility indicated by relatively high densities.
Nucleophilic Substitution in Benzylic Phosphonamidothioic Chlorides: Influence of Substituents on the Elimination-Addition Pathway
Harger, Martin J. P.,Hurman, Barbara T.
, p. 490 - 491 (2007/10/03)
The elimination-addition pathway that competes with SN2(P) in the reaction of ArCH2P(S)(NMe2)CI with Et2NH is very sensitive to the acidity of the benzylic C - H bond (p 3.45).
