2-[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-phenylamino]-3-methyl-butyric acid methyl ester | 168965-60-4

• 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: 2-[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-phenylamino]-3-methyl-butyric acid methyl ester
• CAS: 168965-60-4
• 化学式: C₂₀H₃₂N₂O₅
• 分子量: 380.484
• InChiKey: JWXDTOZGIJYKED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  96.89
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-phenylamino]-3-methyl-butyric acid methyl ester 在 吡啶 、 氢氧化钾 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 120.0h， 生成 Acetic acid (2R,5R)-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：

  diethyl 2-acetamido-2-(2-nitrobenzyl)malonate 在 palladium on activated charcoal 盐酸 、 sodium hydroxide 、 锂硼氢 、 氯化亚砜 、 水 、 氢气 、 sodium cyanoborohydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 126.17h， 生成 2-[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-phenylamino]-3-methyl-butyric acid methyl 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