氢化诺卜基3同烷基卤化铵的合成与结构分析

The Synthesis and Structural Analysis for Hydronopyl Tri-Alkyl Ammonium Halides

将以β-蒎烯为初始原料依次经Prins反应、催化氢化、卤代等合成反应得到的氢化诺卜基卤代物分别与三甲胺、三乙胺、三正丁胺反应,制得氢化诺卜基三甲基卤化铵、氢化诺卜基三乙基卤化铵和氢化诺卜基三正丁基卤化铵共8种含氢化诺卜基的季铵盐类化合物,并对它们的结构进行了质谱、核磁共振及红外光谱分析.其中的氢化诺卜基三乙基碘化铵及氢化诺卜基三正丁基溴化铵在体外抗肿瘤活性试验中表现出对人肺癌H460细胞、人胃癌MKN-45细胞、人肝癌SMMC-7721细胞、人乳腺癌MCF7细胞具有体外抗肿瘤活性.

Hydronopyl halides were synthesized from β-pinene by Prins reaction,catalytic hydrogenation and halogenation,sequentially. There were eight hydronopyl quaternary ammonium salts（ QAS）,which named hydronopyl trimethyl ammonium halide（ chloride,bromide,iodide）,hydronopyl triethyl ammonium halide（ chloride,bromide,iodide） and hydronopyl tributhyl ammonium halide（ chloride,bromide,iodide）,were prepared by hydronopyl halides with trimethylamine,triethylamine and tributylamine,respectively. Identification and structural analysis were done using MS,NMR and IR methods. Anti-tumor activity in vitro test results showed that hydronopyl triethyl ammonium iodide and hydronopyl tributhyl ammonium bromide had anti-tumor activity in vitro on human lung carcinoma cell line H460,human gastric cancer cell line MNK-45,human hepatoma cell line SMMC-7721 and human breast cancer cell line MCF-7.