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The reaction of ethyl diazoacetate with the N-ethoxycarbonyl-N-(2,2,2-trichloroethylidene)amine yields, by a nucleophilic addition, a new diazo compound that gives 1,3-dipolar cycloaddition reactions with acetylenic esters and maleimides. With acetylenic esters, the cycloadduct leads to substituted pyrazoles by [1,5] sigmatropic rearrangements. With maleimides, we observe a diastereospecific cycloaddition reaction. The intermediary cycloadduct evolves by nitrogen elimination to give a maleimidocyclopropane. The diastereospecificity was explained by an endo-anti approach of the reactants.
- Belaissaoui, Abdelhak,Jacquot, Sandrine,Morpain, Claude,Schmitt, Gerard,Vebrel, Joel,Laude, Bernard
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- Discovery of a dual tubulin polymerization and cell division cycle 20 homologue inhibitor via structural modification on apcin
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Apcin is one of the few compounds that have been previously reported as a Cdc20 specific inhibitor, although Cdc20 is a very promising drug target. We reported here the design, synthesis, and biological evaluations of 2,2,2-trichloro-1-aryl carbamate derivatives as Cdc20 inhibitors. Among these derivatives, compound 9f was much more efficient than the positive compound apcin in inhibiting cancer cell growth, but it had approximately the same binding affinity with apcin in SPR assays. It is possible that another mechanism of action might exist. Further evidence demonstrated that compound 9f also inhibited tubulin polymerization, disorganized the microtubule network, and blocked the cell cycle at the M phase with changes in the expression of cyclins. Thus, it induced apoptosis through the activation of caspase-3 and PARP. In addition, compound 9f inhibited cell migration and invasion in a concentration-dependent manner. These results provide guidance for developing the current series as potential new anticancer therapeutics.
- Huang, Pan,Le, Xiangyang,Huang, Fei,Yang, Jie,Yang, Haofeng,Ma, Junlong,Hu, Gaoyun,Li, Qianbin,Chen, Zhuo
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p. 4685 - 4700
(2020/06/08)
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- Expedient synthesis of perhaloaldehyde N-acyl hemiaminals
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Various perhaloaldehyde N-acyl hemiaminals 1 are readily prepared in high yields by condensation of amides 7 with easily available perhaloaldehyde O-ethyl hemiacetals 8 or hydrates 9 in the presence of 5 A molecular sieves.
- Ingrassia, Laurent,Mulliez, Michel
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p. 1731 - 1738
(2007/10/03)
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- Synthesis of α-(acylamino)polyhaloalkylphosphoryl compounds by the reaction of trivalent phosphorus chlorides with N-(α-hydroxypolyhaloalkyl)amides
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N-(α-Hydroxypolyhaloalkyl)amides react with trivalent phosphorus chlorides to give α-(acylamino)polyhaloalkylphosphoryl compounds via phosphorotropic rearrangement of intermediate phosphites or phosphinites.
- Onys'ko
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p. 1763 - 1767
(2007/10/03)
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