5-(p-methoxyphenyl)benzoxepine | 128039-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 5-(p-methoxyphenyl)benzoxepine
• 英文别名: 10-(4-methoxyphenyl)dibenzo[b,f]oxepine；5-(p-methoxyphenyl)dibenz(b,f)oxepin；5-(4-Methoxyphenyl)benzo[b][1]benzoxepine
• CAS: 128039-27-0
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: PLSQPRVPCMYCIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(p-methoxyphenyl)benzoxepine 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 4-(2-(4-(dibenzo[b,f]oxepin-10-yl)phenoxy)ethyl)morpholine
  参考文献：
  名称：

  Synthesis of targeted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines as potential lead molecules with promising anti-breast cancer activity

  摘要：

  A targeted library of substituted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines (prototypes I, II and III), and structurally analogous to tamoxifen have been synthesized as a new class of anti-breast cancer agents. All the prototype molecules exhibited potential antiproliferative activity against ER + ve and ER-ye breast cancer cell lines. Dibenzo[b,f]thiepine prototypes were found to be more active. Of all the compound tested, 14b exhibited potent in-vitro antiproliferative activity at 133 mu M and 5 mu M concentration in MCF-7 and MDA-MB-231 cell lines and was devoid of any cytotoxicity in normal HEK cells even at 50 mu M. Cell cycle analysis showed that the compound 14b inhibited cell proliferation due to G0/G1 arrest in MCF-7 cells. Annexin-V FITC and PI staining experiments confirmed that the cell inhibition was primarily due to apoptosis and not by necrosis, which was also supported by LDH release assay experiment. Molecular docking studies showed better binding interaction of the new dibenzo[b,f]thiepine analogue 14b with the estrogen receptor (ER) as compared to 4-hydroxy-tamoxifen and this enhanced binding might be responsible for its estrogen antagonistic activity that induces cell cycle arrest, apoptosis and inhibition of breast cancer cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.035
• 作为产物：
  描述：

  邻苯氧基苯甲醇 在 吡啶 、 正丁基锂 、 氯化亚砜 、 草酰氯 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 54.0h， 生成 5-(p-methoxyphenyl)benzoxepine
  参考文献：
  名称：

  Synthesis of targeted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines as potential lead molecules with promising anti-breast cancer activity

  摘要：

  A targeted library of substituted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines (prototypes I, II and III), and structurally analogous to tamoxifen have been synthesized as a new class of anti-breast cancer agents. All the prototype molecules exhibited potential antiproliferative activity against ER + ve and ER-ye breast cancer cell lines. Dibenzo[b,f]thiepine prototypes were found to be more active. Of all the compound tested, 14b exhibited potent in-vitro antiproliferative activity at 133 mu M and 5 mu M concentration in MCF-7 and MDA-MB-231 cell lines and was devoid of any cytotoxicity in normal HEK cells even at 50 mu M. Cell cycle analysis showed that the compound 14b inhibited cell proliferation due to G0/G1 arrest in MCF-7 cells. Annexin-V FITC and PI staining experiments confirmed that the cell inhibition was primarily due to apoptosis and not by necrosis, which was also supported by LDH release assay experiment. Molecular docking studies showed better binding interaction of the new dibenzo[b,f]thiepine analogue 14b with the estrogen receptor (ER) as compared to 4-hydroxy-tamoxifen and this enhanced binding might be responsible for its estrogen antagonistic activity that induces cell cycle arrest, apoptosis and inhibition of breast cancer cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.035

文献信息

• Kitamura, Tsugio; Takachi, Tatsuya; Kawasato, Hironobu, Journal of the Chemical Society. Perkin transactions I, 1992, # 15, p. 1969 - 1974
  作者：Kitamura, Tsugio、Takachi, Tatsuya、Kawasato, Hironobu、Taniguchi, Hiroshi

  DOI：——

  日期：——
• Electrophilic addition to o-ArY-substituted phenylalkynes. A highly selective cyclization controlled by heteroatoms
  作者：Tsugio Kitamura、Tatsuya Takachi、Hironobu Kawasato、Shinjiro Kobayashi、Hiroshi Taniguchi

  DOI：10.1016/s0040-4039(00)70720-9

  日期：1989.1