Azelainsaeureanilid | 73148-09-1

• 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: Azelainsaeureanilid
• 英文别名: 8-phenylcarbamoyl-octanoic acid；Azelainsaeure-monoanilid；8-Phenylcarbamoyl-octansaeure；Azelainanilsaeure；9-Anilino-9-oxononanoic acid；9-anilino-9-oxononanoic acid
• CAS: 73148-09-1
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: KUWCRUFJGHCTOW-UHFFFAOYSA-N

物化性质

• 沸点：
  496.0±28.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  9
• 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：

  Azelainsaeureanilid 在 palladium on activated charcoal 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 8-(2-Bromo-acetylamino)-octanoic acid phenylamide
  参考文献：
  名称：

  Novel histone deacetylase inhibitors: design, synthesis, enzyme inhibition, and binding mode study of SAHA-Based non-hydroxamates

  摘要：

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, a series of compounds modeled after suberoylanilide hydroxamic acid (SAHA) were designed and synthesized as (i) substrate (acetyl lysine) analogues (compounds 3-7), (ii) analogues bearing various functional groups expected to chelate zinc ion (compounds 8-15), and (iii) analogues bearing nucleophilic functional groups which could bind covalently to HDACs (compounds 16-18). In this series, semicarbazide 8b and bromoacetamides 18b,c were found to be potent HDAC inhibitors for non-hydroxamates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.048
• 作为产物：
  描述：

  壬二酸氢甲酯 在 lithium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 Azelainsaeureanilid
  参考文献：
  名称：

  基于巯基酰胺的非异羟肟酸型组蛋白脱乙酰基酶抑制剂。

  摘要：

  组蛋白脱乙酰基酶（HDAC）的抑制剂正在作为一种有前途的抗癌药出现。将巯基酰胺官能团设计为双齿锌螯合剂，并掺入基于异羟肟酸的SAHA（1）支架中，以鉴定非异羟肟酸酯化合物作为组蛋白脱乙酰基酶的潜在抑制剂。合成了两组具有不同间隔长度的巯基酰胺2和3，并评估了其对HDAC的抑制活性。巯基酰胺2e，3b和3d的微摩尔抑制作用较低。

  DOI：

  10.1016/j.bmcl.2005.02.075

文献信息

• Studies of Polymerization and Ring Formation. XX. Many-Membered Cyclic Esters
  作者：Julian W. Hill、Wallace H. Carothers

  DOI：10.1021/ja01339a055

  日期：1933.12
• Mercaptoamide-based non-hydroxamic acid type histone deacetylase inhibitors
  作者：Sampath-Kumar Anandan、John S. Ward、Richard D. Brokx、Mark R. Bray、Dinesh V. Patel、Xiao-Xi Xiao

  DOI：10.1016/j.bmcl.2005.02.075

  日期：2005.4

  Inhibitors of histone deacetylases (HDAC) are emerging as a promising class of anti-cancer agents. A mercaptoamide functionality was designed as a bidentate zinc chelator and incorporated into the hydroxamic acid based SAHA (1) scaffold in order to identify non-hydroxamate compounds as potential inhibitors of histone deacetylases. Two sets of mercaptoamides 2 and 3 with varying spacer length were synthesized

  组蛋白脱乙酰基酶（HDAC）的抑制剂正在作为一种有前途的抗癌药出现。将巯基酰胺官能团设计为双齿锌螯合剂，并掺入基于异羟肟酸的SAHA（1）支架中，以鉴定非异羟肟酸酯化合物作为组蛋白脱乙酰基酶的潜在抑制剂。合成了两组具有不同间隔长度的巯基酰胺2和3，并评估了其对HDAC的抑制活性。巯基酰胺2e，3b和3d的微摩尔抑制作用较低。
• Novel histone deacetylase inhibitors: design, synthesis, enzyme inhibition, and binding mode study of SAHA-Based non-hydroxamates
  作者：Takayoshi Suzuki、Yuki Nagano、Azusa Matsuura、Arihiro Kohara、Shin-ichi Ninomiya、Kohfuku Kohda、Naoki Miyata

  DOI：10.1016/j.bmcl.2003.09.048

  日期：2003.12

  In order to find novel non-hydroxamate histone deacetylase (HDAC) inhibitors, a series of compounds modeled after suberoylanilide hydroxamic acid (SAHA) were designed and synthesized as (i) substrate (acetyl lysine) analogues (compounds 3-7), (ii) analogues bearing various functional groups expected to chelate zinc ion (compounds 8-15), and (iii) analogues bearing nucleophilic functional groups which could bind covalently to HDACs (compounds 16-18). In this series, semicarbazide 8b and bromoacetamides 18b,c were found to be potent HDAC inhibitors for non-hydroxamates. (C) 2003 Elsevier Ltd. All rights reserved.