4-(8-methoxy-8-oxooctanamido)benzoyl-ββImImPyγImPyPyβDp | 1203576-86-6

• 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: 4-(8-methoxy-8-oxooctanamido)benzoyl-ββImImPyγImPyPyβDp
• CAS: 1203576-86-6
• 化学式: C₆₇H₈₈N₂₂O₁₄
• 分子量: 1425.57
• InChiKey: DPFVBBWLPAOONU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  103.0
• 可旋转键数：
  38.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  446.99
• 氢给体数：
  12.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  4-(8-methoxy-8-oxooctanamido)benzoyl-ββImImPyγImPyPyβDp 在 羟胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以26%的产率得到SAHA-ββImImPyγImPyPyβDp
  参考文献：
  名称：

  Synthesis and properties of PI polyamide–SAHA conjugate

  摘要：

  We have designed and synthesized new types of pyrrole (P)-imidazole (1) polyamide conjugates 1 and 2 possessing a suberoylanilide hydroxamic acid (SAHA) moiety that is a Strong inhibitor of histone deacetylase (HDAC). SAHA conjugate 2 was designed to target the Promoter region of the p16 tumor suppressor gene. The DNA binding affinity of SAHA conjugate 2 to its target sequence was examined using surface plasmon resonance. HDAC inhibition activity of conjugates 1 and 2 was evaluated using a colorimetric assay. The results demonstrated that even though it possesses the relatively large SAHA moiety, conjugate 2 has high DNA sequence-specific binding properties and moderate HDAC inhibitory activity in vitro. SAHA conjugate 2 was found to cause morphological changes in HeLa cells and to induce selective Histone H3 lysine 9 acetylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.034
• 作为产物：
  描述：

  4-(8-methoxy-8-oxooctanamido)benzoic acid 、 NH2ββImImPyγImPyPyβDp 在 五氟苯基二苯基磷酸酯 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以19%的产率得到4-(8-methoxy-8-oxooctanamido)benzoyl-ββImImPyγImPyPyβDp
  参考文献：
  名称：

  Synthesis and properties of PI polyamide–SAHA conjugate

  摘要：

  We have designed and synthesized new types of pyrrole (P)-imidazole (1) polyamide conjugates 1 and 2 possessing a suberoylanilide hydroxamic acid (SAHA) moiety that is a Strong inhibitor of histone deacetylase (HDAC). SAHA conjugate 2 was designed to target the Promoter region of the p16 tumor suppressor gene. The DNA binding affinity of SAHA conjugate 2 to its target sequence was examined using surface plasmon resonance. HDAC inhibition activity of conjugates 1 and 2 was evaluated using a colorimetric assay. The results demonstrated that even though it possesses the relatively large SAHA moiety, conjugate 2 has high DNA sequence-specific binding properties and moderate HDAC inhibitory activity in vitro. SAHA conjugate 2 was found to cause morphological changes in HeLa cells and to induce selective Histone H3 lysine 9 acetylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.034