(2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-2,4-dienoic acid | 1208355-94-5

• 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)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-2,4-dienoic acid
• CAS: 1208355-94-5
• 化学式: C₁₈H₂₅NO₃
• 分子量: 303.401
• InChiKey: HLRQXRYKWAWZFP-BPLLCVTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-2,4-dienoic acid 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.25h， 以94%的产率得到(+)-trichostatic acid
  参考文献：
  名称：

  An Efficient Synthesis of (±)-Trichostatic Acid and Analogues: A New Route to (±)-Trichostatin A

  摘要：

  An efficient synthesis of rac-trichostatic acid (1) and its analogues Is reported starting from a commercially available aldehyde. Further manipulations of rac-1 led to rac-trichostatin A (TSA). Construction of the desired molecular architecture entails a two-component union, achieved through an in situ hydroboration followed by a Suzuki-Miyaura coupling with 2. The requisite homopropargyl alcohol was synthesized by exploiting allenylindium chemistry. This new protocol paved the way for the synthesis of analogues of trichostatic acid and hence TSA.

  DOI：

  10.1021/ol9029116
• 作为产物：
  描述：

  methyl (2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-2,4-dienoate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以100%的产率得到(2E,4E)-7-[4-(dimethylamino)phenyl]-7-methoxy-4,6-dimethylhepta-2,4-dienoic acid
  参考文献：
  名称：

  An Efficient Synthesis of (±)-Trichostatic Acid and Analogues: A New Route to (±)-Trichostatin A

  摘要：

  An efficient synthesis of rac-trichostatic acid (1) and its analogues Is reported starting from a commercially available aldehyde. Further manipulations of rac-1 led to rac-trichostatin A (TSA). Construction of the desired molecular architecture entails a two-component union, achieved through an in situ hydroboration followed by a Suzuki-Miyaura coupling with 2. The requisite homopropargyl alcohol was synthesized by exploiting allenylindium chemistry. This new protocol paved the way for the synthesis of analogues of trichostatic acid and hence TSA.

  DOI：

  10.1021/ol9029116

文献信息

• Inhibitors of Histone Deacetylase
  申请人：Delorme Daniel

  公开号：US20090181971A1

  公开（公告）日：2009-07-16

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制组蛋白去乙酰化酶的技术。本发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了治疗细胞增殖性疾病和病状的组合物和方法。
• INHIBITORS OF HISTONE DEACETYLASE
  申请人：Methylgene, Inc.

  公开号：EP1280764B1

  公开（公告）日：2010-11-24
• US7288567B2
  申请人：——

  公开号：US7288567B2

  公开（公告）日：2007-10-30
• An Efficient Synthesis of (±)-Trichostatic Acid and Analogues: A New Route to (±)-Trichostatin A
  作者：Anamitra Chatterjee、Joshua Richer、Tyler Hulett、Vijaya Bhaskara Reddy Iska、Olaf Wiest、Paul Helquist

  DOI：10.1021/ol9029116

  日期：2010.2.19

  An efficient synthesis of rac-trichostatic acid (1) and its analogues Is reported starting from a commercially available aldehyde. Further manipulations of rac-1 led to rac-trichostatin A (TSA). Construction of the desired molecular architecture entails a two-component union, achieved through an in situ hydroboration followed by a Suzuki-Miyaura coupling with 2. The requisite homopropargyl alcohol was synthesized by exploiting allenylindium chemistry. This new protocol paved the way for the synthesis of analogues of trichostatic acid and hence TSA.