(2R,5S)-9-decyl-5-(hydroxymethyl)-2-isopropyl-1-methyl-2,4,5,6-tetrahydro-1,4-benzodiazocin-3-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,5S)-9-decyl-5-(hydroxymethyl)-2-isopropyl-1-methyl-2,4,5,6-tetrahydro-1,4-benzodiazocin-3-one
• 英文别名: (2R,5S)-9-decyl-5-(hydroxymethyl)-1-methyl-2-propan-2-yl-2,4,5,6-tetrahydro-1,4-benzodiazocin-3-one
• 化学式: C₂₅H₄₂N₂O₂
• 分子量: 402.621
• InChiKey: NAFNDRDUGFOXIC-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,5S)-9-decyl-5-(hydroxymethyl)-2-isopropyl-1-methyl-2,4,5,6-tetrahydro-1,4-benzodiazocin-3-one 在 吡啶 作用下， 反应 4.0h， 以98%的产率得到Acetic acid (2R,5S)-9-decyl-2-isopropyl-1-methyl-3-oxo-1,2,3,4,5,6-hexahydro-benzo[e][1,4]diazocin-5-ylmethyl ester
  参考文献：
  名称：

  Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins

  摘要：

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.

  DOI：

  10.1021/ja953578v
• 作为产物：
  描述：

  [2-(2-Amino-4-decyl-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal 2,6-二甲基吡啶 、 硼烷 、 氢气 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 乙腈 为溶剂， 生成 (2R,5S)-9-decyl-5-(hydroxymethyl)-2-isopropyl-1-methyl-2,4,5,6-tetrahydro-1,4-benzodiazocin-3-one
  参考文献：
  名称：

  Designed molecules reproducing the two conformations of teleocidins.

  摘要：

  Tumor-promoting teleocidins are known to exist in an equilibrium between two conformational states, the twist form and sofa form, in solution. Benzolactam-Vs, in which the indole ring of indolactams was replaced with a benzene ring, were designed in an attempt to reproduce the active conformation of teleocidins, and synthesized. The 8-membered lactam (benzolactam-V8-310) exists only in the twist form in solution and the 9-membered lactam (benzolactam-V9-310) exists only in the sofa form in solution. The stronger biological activities of the 8-membered lactam than those of indolactam-V and the lack of activity of the 9-membered lactam clearly indicated that active conformation for tumor-promoting activity of teleocidins is close to the twist form.

  DOI：

  10.1016/s0040-4039(00)61468-5

文献信息

• Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure−Activity Studies of Teleocidins
  作者：Yasuyuki Endo、Michihiro Ohno、Masaaki Hirano、Akiko Itai、Koichi Shudo

  DOI：10.1021/ja953578v

  日期：1996.1.1

  Tumor-promoter teleocidins and their active congeners (indolactams) are known to exist in an equilibrium between at least two conformational states in solution, the twist and sofa form, due to cis-trans isomerization of the amide bond and the steric effects of substituents on the nine-membered lactam ring. Benzolactam-Vs, in which the indole ring of indolactams is replaced with a benzene ring, were designed and synthesized in an attempt to reproduce the active conformation of teleocidins. Among these benzolactams, eight-membered lactams (benzolactam-V8) can only exist in the twist form, and 9- and 10-membered lactams (benzolactam-V9 and -V10) exist exclusively in the sofa form in solution. The stronger biological activity of benzolactam-V-8-310 than that of indolactam-V (IL-V) and the inactivity of benzolactam-V-9-310 for differentiation inducing activity of HL-60 clearly indicated that the twist form is close to the active conformation of teleocidins.
• Designed molecules reproducing the two conformations of teleocidins.
  作者：Michihiro Ohno、Yasuyuki Endo、Masaaki Hirano、Akiko Itai、Koichi Shudo

  DOI：10.1016/s0040-4039(00)61468-5

  日期：1993.12

  Tumor-promoting teleocidins are known to exist in an equilibrium between two conformational states, the twist form and sofa form, in solution. Benzolactam-Vs, in which the indole ring of indolactams was replaced with a benzene ring, were designed in an attempt to reproduce the active conformation of teleocidins, and synthesized. The 8-membered lactam (benzolactam-V8-310) exists only in the twist form in solution and the 9-membered lactam (benzolactam-V9-310) exists only in the sofa form in solution. The stronger biological activities of the 8-membered lactam than those of indolactam-V and the lack of activity of the 9-membered lactam clearly indicated that active conformation for tumor-promoting activity of teleocidins is close to the twist form.