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Nitroxyl기가 포함된 Nitrosourea의 합성
Two kinds of nitroxyl radical as carrier of alkylating agents were attached to biologically active moiety 3-N-chloroethylnitroso carbamoyl group, 3-N-methylnitrosocarbamoyl group. 2,2,6,6-tetramethyl-4-oxopiperidine 9 was synthesized by the treatment of starting naterial phorone with ammonia. Intermediate 1-oxyl-2,2,6,6-tetramethyl-4-piperidone 10 was prepared by oxidation of 9. to were treated with ammonium acetate and sodium borohydride which is reduction agent at room temperature to give 4- amino-2.2,6,6-tetramethylpiperidine-1-oxyl 11, and bis (2,2,6,6-tetramethyl piperidine-oxyl-4-yl) 12. N-methyl-N'-(2,2.6,6-tetramethylpiperidine-oxyl -4-yl)urea l3 and N-methyl-N'-[bis(2,2,6,6-tetramethylpiperidine-1-okyl-4- yl]urea were synthlesized by the treatment of 11, l2 with methyl isocyanate respectively. N-methyl-N'-(2,2,6,6-tetramethylpiperdine-1-oxyl-4-yl)-N- nitrosourea 14 and N-met01-N'-[bis(2,2,6.6-tetramethylpiperidine-1-oxyl-4- yl)] nitrosourea were obtained by the reaction of l3, 15 and NaNO_(2) in acetic acid at below 0℃. All melting points were determined on a Bu"chi 510 melting point apparatus. Infrared spectra were recorded on a Perkin-Elmer 683 spectrophotormeter. Mass spectra were recgrded on a Hewlett Packard 5985A GC/MS and KRATOS MS25RFA. EPR spectra were recorded ona Varian E-Line Century series EPR spectrometer. NMR spectra was recorded on a Varian EM360A spectrometer.