2-ethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one | 1610422-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-ethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one
• 英文别名: 7-ethoxy-1-benzosuberone；2-Ethoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one；2-ethoxy-6,7,8,9-tetrahydrobenzo[7]annulen-5-one
• CAS: 1610422-56-4
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: ZTEZREHSTRFDJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-ethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one 在 盐酸 、 sodium methylate 、 magnesium 、 pyridinium hydrobromide perbromide 、 1,2-二溴乙烷 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 二丁醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.75h， 生成 3-ethoxy-6,7-dihydro-8-phenyl-9-(4-hydroxyphenyl)-5H-benzocycloheptene
  参考文献：
  名称：

  Influence of the Length and Positioning of the Antiestrogenic Side Chain of Endoxifen and 4-Hydroxytamoxifen on Gene Activation and Growth of Estrogen Receptor Positive Cancer Cells

  摘要：

  Tamoxifen has biologically active metabolites: 4-hydroxytamoxifen (4OHT) and endoxifen. The E-isomers are not stable in solution as Z-isomerization occurs. We have synthesized fixed ring (FR) analogues of 4OHT and endoxifen as well as FR E and Z isomers with methoxy and ethoxy side chains. Pharmacologic properties were documented in the MCF-7 cell line, and prolactin synthesis was assessed in GH3 rat pituitary tumor cells. The FR Z-isomers of 4OHT and endoxifen were equivalent to 4OHT and endoxifen. Other test compounds used possessed partial estrogenic activity. The E-isomers of FR 4OHT and endoxifen had no estrogenic activity at therapeutic serum concentrations. None of the newly synthesized compounds were able to down-regulate ER levels. Molecular modeling demonstrated that some compounds would each create a best fit with a novel agonist conformation of the ER The results demonstrate modulation by the ER complex of cell replication or gene transcription in cancer.

  DOI：

  10.1021/jm500569h
• 作为产物：
  描述：

  2-甲氧基苯并环庚-5-酮 在 aluminum (III) chloride 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 2-ethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one
  参考文献：
  名称：

  Influence of the Length and Positioning of the Antiestrogenic Side Chain of Endoxifen and 4-Hydroxytamoxifen on Gene Activation and Growth of Estrogen Receptor Positive Cancer Cells

  摘要：

  Tamoxifen has biologically active metabolites: 4-hydroxytamoxifen (4OHT) and endoxifen. The E-isomers are not stable in solution as Z-isomerization occurs. We have synthesized fixed ring (FR) analogues of 4OHT and endoxifen as well as FR E and Z isomers with methoxy and ethoxy side chains. Pharmacologic properties were documented in the MCF-7 cell line, and prolactin synthesis was assessed in GH3 rat pituitary tumor cells. The FR Z-isomers of 4OHT and endoxifen were equivalent to 4OHT and endoxifen. Other test compounds used possessed partial estrogenic activity. The E-isomers of FR 4OHT and endoxifen had no estrogenic activity at therapeutic serum concentrations. None of the newly synthesized compounds were able to down-regulate ER levels. Molecular modeling demonstrated that some compounds would each create a best fit with a novel agonist conformation of the ER The results demonstrate modulation by the ER complex of cell replication or gene transcription in cancer.

  DOI：

  10.1021/jm500569h