5-benzyloxy-7,8-dichloro-6-ethoxy-1,2,3,4-tetrahydro-isoquinoline | 1429254-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 5-benzyloxy-7,8-dichloro-6-ethoxy-1,2,3,4-tetrahydro-isoquinoline
• 英文别名: 7,8-Dichloro-6-ethoxy-5-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline；7,8-dichloro-6-ethoxy-5-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS: 1429254-21-6
• 化学式: C₁₈H₁₉Cl₂NO₂
• 分子量: 352.26
• InChiKey: ZOKBVSYKGXLNSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-氯-N-(6-甲基吡啶-2-基)烟酰胺 、 5-benzyloxy-7,8-dichloro-6-ethoxy-1,2,3,4-tetrahydro-isoquinoline 以 异丙醇 为溶剂， 反应 48.0h， 以18%的产率得到6-(7,8-dichloro-6-ethoxy-5-phenylmethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-N-(6-methylpyridin-2-yl)pyridine-3-carboxamide
  参考文献：
  名称：

  SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer

  摘要：

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.

  DOI：

  10.1021/jm3014103
• 作为产物：
  描述：

  5-benzyloxy-6-ethoxy-1,2,3,4-tetrahydro-isoquinoline 在 氯化亚砜 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以62%的产率得到5-benzyloxy-7,8-dichloro-6-ethoxy-1,2,3,4-tetrahydro-isoquinoline
  参考文献：
  名称：

  SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer

  摘要：

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.

  DOI：

  10.1021/jm3014103

文献信息

• SAR Based Design of Nicotinamides as a Novel Class of Androgen Receptor Antagonists for Prostate Cancer
  作者：Su Hui Yang、Chin-Hee Song、Hue Thi My Van、Eunsook Park、Daulat Bikram Khadka、Eun-Yeung Gong、Keesook Lee、Won-Jea Cho

  DOI：10.1021/jm3014103

  日期：2013.4.25

  Molecular knowledge of pure antagonism and systematic SAR study offered a direction for structural optimization of DIMN to provide nicotinamides as a novel series of AR antagonists. Nicotinamides with extended linear scaffold bearing sterically bulky alkoxy groups on isoquinoline end were synthesized for H12 displacement AR binding affinity and molecular basis of antiandrogenic effect establish the optimized derivatives, 7au and 7bb, as promising candidates of second generation AR antagonists for advanced prostate cancer.