8-Anilino-2-methyl-8-oxooctanoic acid | 939399-95-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-Anilino-2-methyl-8-oxooctanoic acid
• 英文别名: 8-anilino-2-methyl-8-oxooctanoic acid
• CAS: 939399-95-8
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: QAFHJZLNWYVABG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-Anilino-2-methyl-8-oxooctanoic acid 在 N-甲基吗啉 、 羟胺 、 氯甲酸乙酯 作用下， 以 甲醇 为溶剂， 以33%的产率得到N-hydroxy-2-methyl-N'-phenyloctanediamide
  参考文献：
  名称：

  Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid

  摘要：

  Inhibitors of histone deacetylase (HDAC) proteins such as suberoylanilide hydroxamic acid (SAHA) have emerged as effective therapeutic anti-cancer agents. To better understand the structural requirements of HDAC inhibitors, a small molecule library with a variety of substituents attached adjacent to the metal binding hydroxamic acid of SAHA was synthesized. The presence of a substituent adjacent to the hydroxamic acid led to an 800- to 5000-fold decrease in inhibition compared to SAHA. The observed results have implications for drug design, suggesting that HDAC inhibitors with substituents near the metal binding moiety will have inhibitory activities in the micromolar rather than nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.117
• 作为产物：
  描述：

  6-oxo-6-(phenylamino)hexyl methanesulfonate 在 sodium hydroxide 、 sodium hydride 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 二甲基亚砜 为溶剂， 生成 8-Anilino-2-methyl-8-oxooctanoic acid
  参考文献：
  名称：

  Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid

  摘要：

  Inhibitors of histone deacetylase (HDAC) proteins such as suberoylanilide hydroxamic acid (SAHA) have emerged as effective therapeutic anti-cancer agents. To better understand the structural requirements of HDAC inhibitors, a small molecule library with a variety of substituents attached adjacent to the metal binding hydroxamic acid of SAHA was synthesized. The presence of a substituent adjacent to the hydroxamic acid led to an 800- to 5000-fold decrease in inhibition compared to SAHA. The observed results have implications for drug design, suggesting that HDAC inhibitors with substituents near the metal binding moiety will have inhibitory activities in the micromolar rather than nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.117

文献信息

• Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid
  作者：Anton V. Bieliauskas、Sujith V.W. Weerasinghe、Mary Kay H. Pflum

  DOI：10.1016/j.bmcl.2007.01.117

  日期：2007.4

  Inhibitors of histone deacetylase (HDAC) proteins such as suberoylanilide hydroxamic acid (SAHA) have emerged as effective therapeutic anti-cancer agents. To better understand the structural requirements of HDAC inhibitors, a small molecule library with a variety of substituents attached adjacent to the metal binding hydroxamic acid of SAHA was synthesized. The presence of a substituent adjacent to the hydroxamic acid led to an 800- to 5000-fold decrease in inhibition compared to SAHA. The observed results have implications for drug design, suggesting that HDAC inhibitors with substituents near the metal binding moiety will have inhibitory activities in the micromolar rather than nanomolar range. (c) 2007 Elsevier Ltd. All rights reserved.