96014-61-8Relevant articles and documents
4-(3-Halo/amino-4,5-dimethoxyphenyl)-5-aryloxazoles and-N-methylimidazoles That Are cytotoxic against combretastatin a resistant tumor cells and vascular disrupting in a cisplatin resistant germ cell tumor model
Schobert, Rainer,Biersack, Bernhard,Dietrich, Andrea,Effenberger, Katharina,Knauer, Sebastian,Mueller, Thomas
experimental part, p. 6595 - 6602 (2010/11/19)
New combretastatin A analogues featuring oxazole or N-methylimidazole bridged Z-alkenes and halo-or amino-substituted A-rings were tested against various cancer cell lines and in testicular germ cell tumor xenografts in mice. Imidazoles with 3-halo-4,5-dimethoxy substituted A-rings and 3-amino-4-methoxy substituted B-rings (7b and 8b) were efficacious at nanomolar concentrations against cells of combretastatin A refractory HT-29 colon carcinoma, multidrug-resistant MCF-7/Topo breast carcinoma, and cisplatin-resistant 1411HP testicular germ cell tumor. They induced apoptosis and inhibited tubulin polymerization. While well tolerated by mice at high doses, these imidazoles initiated extensive intratumoral hemorrhage and regressions of highly vascularized 1411HP xenografts.
ACTIVATING EFFECT OF THE IMINIUM GROUP IN AROMATIC NUCLEOPHILIC SUBSTITUTION OF AN ALKOXY GROUP AND HALOGEN ATOMS BY THE ACTION OF NITROGEN BASES
Blokhin, A.V.,Bundel, Yu. G.,Terenin, V.I.,Kurtz, A.L.
, p. 2116 - 2123 (2007/10/02)
The characteristics of aromatic nucleophilic substitution with activation by the iminium group in the iminium derivatives of p-alkoxy- and p-halogenobenzaldehydes were investigated.They are determined by the concurrent addition of the nucleophilic agents at the C=N multiple bond.The activating effect of the iminium group depends on the nature of the leaving group, the solvent, the substituent in the benzene ring, and the nature and concentration of the protonating agent.The action of heat on p-methoxybenzylidenemethylamine with a tenfold excess of methylamine hydrochloride in a 30percent alcohol solution of methylamine at 150 deg C for 40 h leads to substitutioon of the methoxymethylamino group with a yield of 90percent.
