methyl 12-(2,3-bis(tert-butoxycarbonyl)-3-methylguanidino)dodecanoate | 878631-25-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 12-(2,3-bis(tert-butoxycarbonyl)-3-methylguanidino)dodecanoate
• CAS: 878631-25-5
• 化学式: C₂₅H₄₇N₃O₆
• 分子量: 485.665
• InChiKey: DTUWYHDIMYHOGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  106.53
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 12-(2,3-bis(tert-butoxycarbonyl)-3-methylguanidino)dodecanoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以72%的产率得到12-(2,3-bis(tert-butoxycarbonyl)-3-methylguanidino)dodecanoic acid
  参考文献：
  名称：

  Structure–activity relationship studies on niphimycin, a guanidylpolyol macrolide antibiotic. Part 1: The role of the N-methyl-N″-alkylguanidinium moiety

  摘要：

  Several N-methyl-N ''-alkylguanidinium derivatives were synthesized and used as simplified analogues of niphimycin (NM), a guanidylpolyol macrolide, in structure-activity relationship studies. The C16-alkylated derivative exerted fungicidal activity by directly damaging the fungal plasma membrane and inducing oxidative stress in a manner similar to niphimycin. These results indicate that the N-methyl-N ''-alkylguanidinium moiety is required for antifungal activity by NM. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.024
• 作为产物：
  描述：

  N,N''-bis(tert-butoxycarbonyl)-1-methyl-2-thiourea 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 methyl 12-(2,3-bis(tert-butoxycarbonyl)-3-methylguanidino)dodecanoate
  参考文献：
  名称：

  Structure–activity relationship studies on niphimycin, a guanidylpolyol macrolide antibiotic. Part 1: The role of the N-methyl-N″-alkylguanidinium moiety

  摘要：

  Several N-methyl-N ''-alkylguanidinium derivatives were synthesized and used as simplified analogues of niphimycin (NM), a guanidylpolyol macrolide, in structure-activity relationship studies. The C16-alkylated derivative exerted fungicidal activity by directly damaging the fungal plasma membrane and inducing oxidative stress in a manner similar to niphimycin. These results indicate that the N-methyl-N ''-alkylguanidinium moiety is required for antifungal activity by NM. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.024