6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid hydroxyamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid hydroxyamide
• 英文别名: 6-[3-1-(adamantyl)-4-methoxyphenyl]-naphthalene-2-carboxylic acid N-hydroxyamide；6-[3-(1-adamantyl)-4-methoxyphenyl]-N-hydroxynaphthalene-2-carboxamide
• 化学式: C₂₈H₂₉NO₃
• 分子量: 427.543
• InChiKey: QLUZYUVPNBWFJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  阿达帕林 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 盐酸羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.03h， 生成 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid hydroxyamide
  参考文献：
  名称：

  WO2007/383

  摘要：

  公开号：

文献信息

• WO2007/383
  申请人：——

  公开号：——

  公开（公告）日：——
• US7728039B2
  申请人：——

  公开号：US7728039B2

  公开（公告）日：2010-06-01
• Influence of the adamantyl moiety on the activity of biphenylacrylohydroxamic acid-based HDAC inhibitors
  作者：Raffaella Cincinelli、Loana Musso、Giuseppe Giannini、Valentina Zuco、Michelandrea De Cesare、Franco Zunino、Sabrina Dallavalle

  DOI：10.1016/j.ejmech.2014.04.021

  日期：2014.5

  To investigate the influence of the adamantyl group on the biological properties of known HDAC inhibitors with a 4-phenylcinnamic skeleton, a series of compounds having the adamantyl moiety in the cap structure were synthesized and compared to the corresponding hydroxamic acids lacking this group. An unexpected finding was the substantial reduction of inhibitory activity toward the tested enzymes, in particular HDAC6, following the introduction of the adamantyl group. In spite of the reduced ability to function as HDAC inhibitors, the compounds containing the adamantyl moiety still retained a good efficacy as antiproliferative and proapoptotic agents. A selected compound (2c; ST3056) of this series exhibited an appreciable antitumor activity against the colon carcinoma xenograft HCT116. (c) 2014 Elsevier Masson SAS. All rights reserved.