(2E,4E)-(R)-6-(4-Dimethylamino-benzoylamino)-hepta-2,4-dienoic acid ethyl ester | 596093-48-0

• 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: (2E,4E)-(R)-6-(4-Dimethylamino-benzoylamino)-hepta-2,4-dienoic acid ethyl ester
• 英文别名: ethyl (2E,4E,6R)-6-[[4-(dimethylamino)benzoyl]amino]hepta-2,4-dienoate
• CAS: 596093-48-0
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: KGHGEUNNSCMXBR-YDBVJNLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-(R)-6-(4-Dimethylamino-benzoylamino)-hepta-2,4-dienoic acid ethyl ester 在 盐酸 作用下， 以 丙酮 为溶剂， 以70%的产率得到(2E,4E)-(R)-6-(4-Dimethylamino-benzoylamino)-hepta-2,4-dienoic acid
  参考文献：
  名称：

  Amide analogues of TSA: synthesis, binding mode analysis and HDAC inhibition

  摘要：

  The synthesis of new amide type historic deacetylase inhibitors is described, having an (R)-methyl substituent and a diene or saturated structure of the chain linking the hydroxamic acid and dimethylaminobenzoyl groups. The saturated compound shows stronger HDAC inhibition than the unsaturated analogue. Molecular modeling suggests that the flexibility of the linker chain is important for an optimal orientation of the dimethylaminobenzoyl group in the enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00284-1
• 作为产物：
  描述：

  ethyl (2E,4E,6R)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hepta-2,4-dienoate 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 三氟乙酸 作用下， 反应 2.0h， 生成 (2E,4E)-(R)-6-(4-Dimethylamino-benzoylamino)-hepta-2,4-dienoic acid ethyl ester
  参考文献：
  名称：

  Amide analogues of TSA: synthesis, binding mode analysis and HDAC inhibition

  摘要：

  The synthesis of new amide type historic deacetylase inhibitors is described, having an (R)-methyl substituent and a diene or saturated structure of the chain linking the hydroxamic acid and dimethylaminobenzoyl groups. The saturated compound shows stronger HDAC inhibition than the unsaturated analogue. Molecular modeling suggests that the flexibility of the linker chain is important for an optimal orientation of the dimethylaminobenzoyl group in the enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00284-1

文献信息

• Amide analogues of TSA: synthesis, binding mode analysis and HDAC inhibition
  作者：K Van Ommeslaeghe、G Elaut、V Brecx、P Papeleu、K Iterbeke、P Geerlings、D Tourwé、V Rogiers

  DOI：10.1016/s0960-894x(03)00284-1

  日期：2003.6

  The synthesis of new amide type historic deacetylase inhibitors is described, having an (R)-methyl substituent and a diene or saturated structure of the chain linking the hydroxamic acid and dimethylaminobenzoyl groups. The saturated compound shows stronger HDAC inhibition than the unsaturated analogue. Molecular modeling suggests that the flexibility of the linker chain is important for an optimal orientation of the dimethylaminobenzoyl group in the enzyme. (C) 2003 Elsevier Science Ltd. All rights reserved.