2-butyl-7-phenylcarbamoyl-heptanoic acid | 939400-01-8

• 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: 2-butyl-7-phenylcarbamoyl-heptanoic acid
• CAS: 939400-01-8
• 化学式: C₁₈H₂₇NO₃
• 分子量: 305.417
• InChiKey: OJUKEHUPDBULNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-butyl-7-phenylcarbamoyl-heptanoic acid 在 N-甲基吗啉 、 羟胺 、 氯甲酸乙酯 作用下， 以 甲醇 为溶剂， 以24%的产率得到2-butyl-N-hydroxy-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：

  5-hydroxy-N-phenylpentanamide 在 sodium hydroxide 、 TEA 、 sodium hydride 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成 2-butyl-7-phenylcarbamoyl-heptanoic 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