1-(N-benzyloxycarbonyl)amino-4-aza-8-aminononane | 1310219-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(N-benzyloxycarbonyl)amino-4-aza-8-aminononane
• CAS: 1310219-10-3
• 化学式: C₁₆H₂₇N₃O₂
• 分子量: 293.409
• InChiKey: KWDPJNMUJCERDT-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  1-(N-benzyloxycarbonyl)amino-4-aza-8-aminononane 在 sodium hydroxide 、 氢气 、 钯 、 溶剂黄146 、 盐酸 作用下， 以 水 、 甲醇 、 乙醇 为溶剂， 以0.4 g的产率得到1,8-diamino-4-azanonane trihydrochloride
  参考文献：
  名称：

  The Use of Novel C-Methylated Spermidine Derivatives To Investigate the Regulation of Polyamine Metabolism

  摘要：

  The polyamines are organic polycations present at millimolar concentrations in eukaryotic cells where they participate in the regulation of vital cellular functions including proliferation and differentiation. Biological evaluation of rationally designed polyamine analogs is one of the cornerstones of polyamine research. Here we have synthesized and characterized novel C-methylated spermidine analogs, that is, 2-methylspermidine, 3-methylspermidine, and 8-methylspermidine. 3-Methylspermidine was found to be metabolically stable in DU145 cells, while 8-methylspermidine was a substrate for spermidine/spermine N(1)-acetyltransferase (SSAT) and 2-methylspermidine was a substrate for both SSAT and acetylpolyamine oxidase. All the analogs induced the splicing of the productive mRNA splice variant of SSAT, overcame growth arrest induced by 72-h treatment with ornithine decarboxylase (ODC), inhibitor alpha-difluoromethylornithine, and were transported via the poly amine transporter. Surprisingly, 2-methylspermidine was a weak downregulator of ODC activity in DU145 cells. Our data demonstrates that it is possible to radically alter the biochemical properties of a polyamine analog by changing the position of the methyl group.

  DOI：

  10.1021/jm200293r