94707-56-9Relevant academic research and scientific papers
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
supporting information; 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.
Quantitative solid-state reactions of amines with carbonyl compounds and isothiocyanates
Kaupp, Gerd,Schmeyers, Jens,Boy, Juergen
, p. 6899 - 6911 (2007/10/03)
A series of solid-state reactions is reported of gaseous or solid amines with aldehydes to give imines, with solid anhydrides to give diamides (therefrom imides) or amidic carboxylic salts or imides, with solid imides to give diamides, with solid lactones or carbonates to give functionalized carbamic esters, with polycarbonates to give degradative aminolysis, and with solid isothiocyanates to give thioureas. Diamides give imides by solid-state thermolysis or acid catalysis. Various double, two-step, 3-cascade, and sequential reactions are reported in the solid state without melting. The yields are quantitative in 53 reported reaction examples and no workup (except for washings in four cases) is required in the 100% yield reactions. Three initially solid-state reactions but with liquid product were not quantitative. An upscaling to the kg scale shows promise of the technique for large scale applications. Supermicroscopic analyses with AFM elucidate the solid-state mechanism by virtue of far-reaching anisotropic molecular movements in three-step processes. Gas-solid aminolyses of polycarbonates are also studied with AFM. The implications to sustainable chemistry are discussed. (C) 2000 Elsevier Science Ltd.
Isoquinolinium Salt Syntheses from Cyclopalladated Benzaldimines and Alkynes
Wu, Guangzhong,Geib, Steven J.,Rheingold, Arnold L.,Heck, Richard F.
, p. 3238 - 3241 (2007/10/02)
Cyclopalladated, N-substituted benzaldimine tetrafluoroborates react with disubstituted alkynes in poor to good yields to form isoquinolinium tetrafluoroborates.The reaction is particularly useful for preparing trisubstituted products.Electron-donating substituens may be presented at the 5, 6, 7, and 8 positions, as well.Methyl (p-benzoxyphenyl)propiolate adds to cyclopalladated N-methyl-3-benzoxy-4-methoxybenzaldimine tetrafluoroborate to form the 3-arylisoquinolinium salt. 3-Hexyne reacts with cyclopalladated N-phenylbenzaldymine chloro dimer at 150 deg C to form the isoquinolinium chloride but at less than half (29percent) the yield that is obtained from the corresponding tetrafluoroborate.
