(3S,6R,7R)-6-Isobutyl-5,18-dioxo-12-oxa-4-aza-tricyclo[11.2.2.1^4,7]octadeca-1(16),13(17),14-triene-3-carboxylic acid (5-benzyloxycarbamoyl-pentyl)-amide | 515163-52-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (3S,6R,7R)-6-Isobutyl-5,18-dioxo-12-oxa-4-aza-tricyclo[11.2.2.1^4,7]octadeca-1(16),13(17),14-triene-3-carboxylic acid (5-benzyloxycarbamoyl-pentyl)-amide
• 英文别名: (3S,6R,7R)-6-(2-methylpropyl)-5,18-dioxo-N-[6-oxo-6-(phenylmethoxyamino)hexyl]-12-oxa-4-azatricyclo[11.2.2.14,7]octadeca-1(16),13(17),14-triene-3-carboxamide
• CAS: 515163-52-7
• 化学式: C₃₄H₄₅N₃O₆
• 分子量: 591.748
• InChiKey: HKHKORAHCPUVLF-OCBJUFRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,6R,7R)-6-Isobutyl-5,18-dioxo-12-oxa-4-aza-tricyclo[11.2.2.1^4,7]octadeca-1(16),13(17),14-triene-3-carboxylic acid (5-benzyloxycarbamoyl-pentyl)-amide 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到(3S,6R,7R)-6-Isobutyl-5,18-dioxo-12-oxa-4-aza-tricyclo[11.2.2.1^4,7]octadeca-1(16),13(17),14-triene-3-carboxylic acid (5-hydroxycarbamoyl-pentyl)-amide
  参考文献：
  名称：

  Succinimide hydroxamic acids as potent inhibitors of histone deacetylase (HDAC)

  摘要：

  A series of succinimide hydroxamic acids was prepared and evaluated in vitro for HDAC inhibition and tumor cell antiproliferation. While the original macrocyclic analogue 6 was quite potent in both assays, several appropriately substituted non-macrocyclic succinimides, such as 23, were equipotent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00622-4
• 作为产物：
  描述：

  (7R,8R,11S)-11-(5-Benzyloxycarbamoyl-pentylcarbamoyl)-8-isobutyl-9-oxo-2-oxa-10-aza-bicyclo[11.2.2]heptadeca-1(16),13(17),14-triene-7-carboxylic acid 在 potassium tert-butylate 、 氯甲酸异丙酯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3S,6R,7R)-6-Isobutyl-5,18-dioxo-12-oxa-4-aza-tricyclo[11.2.2.1^4,7]octadeca-1(16),13(17),14-triene-3-carboxylic acid (5-benzyloxycarbamoyl-pentyl)-amide
  参考文献：
  名称：

  Succinimide hydroxamic acids as potent inhibitors of histone deacetylase (HDAC)

  摘要：

  A series of succinimide hydroxamic acids was prepared and evaluated in vitro for HDAC inhibition and tumor cell antiproliferation. While the original macrocyclic analogue 6 was quite potent in both assays, several appropriately substituted non-macrocyclic succinimides, such as 23, were equipotent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00622-4

文献信息

• Succinimide hydroxamic acids as potent inhibitors of histone deacetylase (HDAC)
  作者：Michael L. Curtin、Robert B. Garland、H.Robin Heyman、Robin R. Frey、Michael R. Michaelides、Junling Li、Lori J. Pease、Keith B. Glaser、Patrick A. Marcotte、Steven K. Davidsen

  DOI：10.1016/s0960-894x(02)00622-4

  日期：2002.10

  A series of succinimide hydroxamic acids was prepared and evaluated in vitro for HDAC inhibition and tumor cell antiproliferation. While the original macrocyclic analogue 6 was quite potent in both assays, several appropriately substituted non-macrocyclic succinimides, such as 23, were equipotent. (C) 2002 Elsevier Science Ltd. All rights reserved.