685-87-0Relevant articles and documents
Orienting effect of the cage addends: The case of nucleophilic cyclopropanation of C2-C70(CF3)8
Apenova, Marina G.,Semivrazhskaya, Olesya O.,Borkovskaya, Eugenia V.,Belov, Nikita M.,Ioffe, Ilya N.,Markov, Vitaliy Yu.,Troyanov, Sergey I.,Lukonina, Natalia S.,Sidorov, Lev N.,Goryunkov, Alexey A.
, p. 1370 - 1378 (2015)
C2-C70(CF3)8 was found to be a very promising substrate in the Bingel and the Bingel-Hirsch reactions combining perfect regioselectivity with much higher reactivity compared to its analogs. The reactions with diethyl malonate yield a single isomer of the monoadduct C70(CF3)8[C(CO2Et)2] and a single C2-symmetrical bisadduct C70(CF3)8[C(CO2Et)2]2. The Bingel-Hirsch variation is particularly interesting in that it additionally affords, in a similar regioselective manner, the unexpected alkylated derivatives C70(CF3)8[CH(CO2Et)2]H and C70(CF3)8[C(CO2Et)2][CH(CO2Et)2]H. The novel compounds have been isolated and structurally characterized by means of 1H and 19F NMR spectroscopy as well as single-crystal X-ray diffraction. The mechanistic and regiochemical aspects of the reaction are explained with the aid of DFT calculations. Conventional vs. unconventional: Acceptor-derivatized fullerene substrates can exhibit an enhanced reactivity and regioselectivity in important organic reactions. Bingel and Bingel-Hirsch functionalization of C2-C70(CF3)8 are reported, which affords rapid and LUMO-directed regioselective formation of both conventional cyclopropanated and unusual alkylated products. The mechanistic and regiochemical aspects of the reaction are explained with the aid of the DFT calculations.
Phenyl pyrimidinamine anti-tumor compound as well as preparation method and application thereof
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Paragraph 0045-0047, (2021/06/06)
The invention belongs to the technical field of medicines, relates to a compound with anti-tumor activity and a specific chemical structure, and particularly relates to a phenyl pyrimidinamine compound as well as a preparation method and application thereof. The structural general formula of the phenyl pyrimidinamine compound is shown in the specification, wherein an R group is a hydrogen atom, a 2-position monosubstituted fluorine atom, or 3-position and 4-position monosubstituted methyl, a fluorine atom, a chlorine atom and a bromine atom. Experimental research shows that the prepared phenyl pyrimidinamine compound shows a good result in an in-vitro anti-tumor activity test, can be used for preparing anti-tumor drugs, and opens up a new way for developing the anti-tumor drugs with an endothelin receptor as a new target. The preparation method provided by the invention is simple and feasible, higher in yield and easy for large-scale production.
Novel Allosteric Inhibitors of Deoxyhypusine Synthase against Malignant Melanoma: Design, Synthesis, and Biological Evaluation
Li, Shuai,Li, Xin-Yang,Li, Yu-Heng,Lin, Qi-Qi,Liu, Kai-Li,Meng, Fan-Hao,Qian, Xin-Hua,Wang, De-Pu,Xue, Wen-Han
, p. 13356 - 13372 (2021/09/20)
Based on the novel allosteric site of deoxyhypusine synthase (DHPS), two series of 30 novel 5-(2-methoxyphenoxy)-2-phenylpyrimidin-4-amine derivatives as DHPS inhibitors were designed and synthesized. Among them, compound8m, with the best DHPS inhibitory potency (IC50= 0.014 μM), exhibited excellent inhibition against melanoma cells, which was superior to that of GC7. Besides, molecular docking and molecular dynamics (MD) simulations further proved that compound8mwas tightly bound to the allosteric site of DHPS. Flow cytometric analysis and enzyme-linked immunosorbent assay (ELISA) showed that compound8mcould inhibit the intracellular reactive oxygen species (ROS) level. Furthermore, by western blot analysis, compound8meffectively activated caspase 3 and decreased the expressions of GP-100, tyrosinase, eIF5A2, MMP2, and MMP9. Moreover, both Transwell analysis and wound healing analysis showed that compound8mcould inhibit the invasion and migration of melanoma cells. In thein vivostudy, the tumor xenograft model showed that compound8meffectively inhibited melanoma development with low toxicity.