4α-hydroxymethyl-7,7-di-n-butyl-5α-methyl-1,3,4,5,5aβ,6,7,8,9,9aα-decahydro-2H-benzazepin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4α-hydroxymethyl-7,7-di-n-butyl-5α-methyl-1,3,4,5,5aβ,6,7,8,9,9aα-decahydro-2H-benzazepin-2-one
• 英文别名: (4S,5aS,9aS)-7,7-Dibutyl-4-hydroxymethyl-5a-methyl-decahydro-benzo[d]azepin-2-one；(2S,5aS,9aS)-8,8-dibutyl-2-(hydroxymethyl)-9a-methyl-1,2,3,5,5a,6,7,9-octahydrobenzo[d]azepin-4-one
• 化学式: C₂₀H₃₇NO₂
• 分子量: 323.519
• InChiKey: CUVHDZLGDFJHNN-JENIJYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4S,5aS,9aS)-7,7-Dibutyl-5a-methyl-4-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-benzo[d]azepin-2-one 在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 生成 4α-hydroxymethyl-7,7-di-n-butyl-5α-methyl-1,3,4,5,5aβ,6,7,8,9,9aα-decahydro-2H-benzazepin-2-one
  参考文献：
  名称：

  Synthesis, computer modeling and biological evaluation of novel protein kinase C agonists based on a 7-membered lactam moiety

  摘要：

  4-Hydroxymethyl-5a-methyl-1,3,4,5,5a beta,6,7,8,9,9a alpha-decahydro-2H-benz[d]azepin-2-one (4-12), which were designed to mimic the biologically active conformation of teleocidins and benzolactams, were synthesized and evaluated for the ability to compete with [H-3]phorbol 12,13-dibutyrate in a PKC delta binding assay. Among the ed potent binding affinity, with inhibition constants (K-i) of low nanomolar order. Computational docking simulation also indicates that the relative positions of the hydrogen-bonding sites and hydrophobic regions of the compounds are well matched to the PKC delta binding site. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00724-0

文献信息

• Synthesis, computer modeling and biological evaluation of novel protein kinase C agonists based on a 7-membered lactam moiety
  作者：Yasuyuki Endo、Masako Shimazu、Hiroshi Fukasawa、Paul E. Driedger、Kaname Kimura、Nobuo Tomioka、Akiko Itai、Koichi Shudo

  DOI：10.1016/s0960-894x(98)00724-0

  日期：1999.1

  4-Hydroxymethyl-5a-methyl-1,3,4,5,5a beta,6,7,8,9,9a alpha-decahydro-2H-benz[d]azepin-2-one (4-12), which were designed to mimic the biologically active conformation of teleocidins and benzolactams, were synthesized and evaluated for the ability to compete with [H-3]phorbol 12,13-dibutyrate in a PKC delta binding assay. Among the ed potent binding affinity, with inhibition constants (K-i) of low nanomolar order. Computational docking simulation also indicates that the relative positions of the hydrogen-bonding sites and hydrophobic regions of the compounds are well matched to the PKC delta binding site. (C) 1999 Elsevier Science Ltd. All rights reserved.