N-butyl-11-[[(3S)-2-(4-methoxybenzoyl)-3,4-dihydro-1H-isoquinolin-3-yl]methoxy]undecanamide | 845833-31-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N-butyl-11-[[(3S)-2-(4-methoxybenzoyl)-3,4-dihydro-1H-isoquinolin-3-yl]methoxy]undecanamide
• CAS: 845833-31-0
• 化学式: C₃₃H₄₈N₂O₄
• 分子量: 536.755
• InChiKey: UHYWRVWTGGCSDL-PMERELPUSA-N

物化性质

• 沸点：
  709.4±60.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-butyl-11-[[(3S)-2-(4-methoxybenzoyl)-3,4-dihydro-1H-isoquinolin-3-yl]methoxy]undecanamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 N-butyl-11-[[(3S)-2-(4-hydroxybenzoyl)-3,4-dihydro-1H-isoquinolin-3-yl]methoxy]undecanamide
  参考文献：
  名称：

  Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer

  摘要：

  A series of tetrahydroisoquinoline-N-phenylamide derivatives were designed, synthesized, and tested for their relative binding affinities, and antagonistic activities against estrogen receptor (ER). Compound If (relative binding affinity, RBA = 5) showed higher binding affinity than tamoxifen (R BA = 1), a potent ER antagonist and currently being used for breast cancer therapy. Compound If also exerted optimal antagonistic activity against ER in reporter and cell proliferation assays. Interestingly, compound Ij, which only has a minor agonistic effect against ER, acted as a progesterone receptor (PR) antagonist and exerted agonistic activity against AP-1 through ER pathway. Our results show that these new compounds can be employed as leading pharmacophore for further development of potent selective ER and/or PR modulators or antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.002
• 作为产物：
  描述：

  11-溴十一酸 在 三正丁胺 、 sodium hydride 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-butyl-11-[[(3S)-2-(4-methoxybenzoyl)-3,4-dihydro-1H-isoquinolin-3-yl]methoxy]undecanamide
  参考文献：
  名称：

  Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer

  摘要：

  A series of tetrahydroisoquinoline-N-phenylamide derivatives were designed, synthesized, and tested for their relative binding affinities, and antagonistic activities against estrogen receptor (ER). Compound If (relative binding affinity, RBA = 5) showed higher binding affinity than tamoxifen (R BA = 1), a potent ER antagonist and currently being used for breast cancer therapy. Compound If also exerted optimal antagonistic activity against ER in reporter and cell proliferation assays. Interestingly, compound Ij, which only has a minor agonistic effect against ER, acted as a progesterone receptor (PR) antagonist and exerted agonistic activity against AP-1 through ER pathway. Our results show that these new compounds can be employed as leading pharmacophore for further development of potent selective ER and/or PR modulators or antagonists. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.002

文献信息

• Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer
  作者：Hsiang-Ru Lin、Martin K. Safo、Donald J. Abraham

  DOI：10.1016/j.bmcl.2007.02.002

  日期：2007.5

  A series of tetrahydroisoquinoline-N-phenylamide derivatives were designed, synthesized, and tested for their relative binding affinities, and antagonistic activities against estrogen receptor (ER). Compound If (relative binding affinity, RBA = 5) showed higher binding affinity than tamoxifen (R BA = 1), a potent ER antagonist and currently being used for breast cancer therapy. Compound If also exerted optimal antagonistic activity against ER in reporter and cell proliferation assays. Interestingly, compound Ij, which only has a minor agonistic effect against ER, acted as a progesterone receptor (PR) antagonist and exerted agonistic activity against AP-1 through ER pathway. Our results show that these new compounds can be employed as leading pharmacophore for further development of potent selective ER and/or PR modulators or antagonists. (c) 2007 Elsevier Ltd. All rights reserved.