G. Gaudiano, E. L. Frank, M. Wysor
Dec 1, 1993
Citations
0
Influential Citations
4
Citations
Journal
Journal of Organic Chemistry
Abstract
Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer) was synthesized by condensing tris(hydroxymethyl)aminomethane with ethyl pyruvate to form 5,6-dihydro-5,5-bis(hydroxymethyl)-3-methyl- 1,4-oxazin-2-one (1) followed by photoreduction in 2-propanol. BHM-3 dimer exists in equilibrium with 5,5-bis(hydroxymethyl)-3-methyl-2-oxo- morpholin-3-yl (BHM-3) in solution; the rate constant for BHM-3 formation from dimers varies with solvent increasing from 5.3×10 -6 s -1 in acetonitrile to 1.5×10 -3 s -1 in water at 25 o C. BHM-3 reacts as a one-electron reducing agent, and the reduction potential for BHM-3 dimer is estimated at -0.54 V vs NHE from the position of equilibrium for the reduction of the viologen, propyldiquat, to its radical cation. BHM-3 dimer has an octanol/water partition coefficient of 0.054 and shows low mouse toxicity even upon intravenous administration. Intravenously administered BHM-3 dimer projects mice from an immediated subsequent lethal injection of the antitumor drug adriamycin.The properties of BHM-3 dimer are compared with those of other 2-oxomorpholin-3-yl dimers