4-(3-methoxy-11H-benzofluoren-11-yl)phenol | 138630-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4-(3-methoxy-11H-benzofluoren-11-yl)phenol
• 英文别名: 4-(3-methoxy-11H-benzo[a]-fluoren-11-yl)phenol；11-(4-hydroxyphenyl)-3-methoxy-11H-benzo[a]fluorene；4-(3-methoxy-11H-benzo[a]fluoren-11-yl)phenol
• CAS: 138630-78-1
• 化学式: C₂₄H₁₈O₂
• 分子量: 338.406
• InChiKey: HJIRBAOWNOYEOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

反应信息

• 作为反应物：
  描述：

  4-(3-methoxy-11H-benzofluoren-11-yl)phenol 在 三氯化铝 、 potassium carbonate 、 乙硫醇 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 11-<4-<2-(1-piperidinyl)ethoxy>phenyl>-11H-benzofluoren-3-ol
  参考文献：
  名称：

  Antiestrogens. 3. Estrogen receptor affinities and antiproliferative effects in MCF-7 cells of phenolic analogs of trioxifene, [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl)ethoxy]phenyl[methanone

  摘要：

  Benzothiophenes 3 and 4, derived from the acrylophenone antiestrogen trioxifene (2), are characterized by high estrogen receptor (ER) affinity and low residual estrogenicity compared to tamoxifen (1a). In order to characterize further the growth suppression mechanism for these structural types we have prepared structural variants of 2 bearing hydroxy groups positioned to maximize ER affinity. Thus, dihydronaphthalenes 5 and 6 and benzofluorenes 7 and 8 were prepared and studied in MCF-7 human breast cancer cells, in comparison with 3 and 4. All compounds were powerful suppressants of cell growth, with 50% inhibition ranging from 4.5 to 160 nM. Greatest potency was seen with diphenols 6 and 8. These compounds had intracellular ER affinities ranging from 0.2 to 4.1% of that of estradiol, suggestive of a potential for partial agonist effects. Simultaneous exposure of cells to 0.1-mu-M concentrations of estradiol and 3 or 4 did not affect the degree of growth inhibition seen with 0.1-mu-M 3 or 4 alone. Partial reversal of inhibition occurred when 0.1-mu-M 5-8 were each accompanied by 0.1-mu-M estradiol. Under these conditions complete reversal of growth inhibition has been found with 1a, 1b, and other triarylethylenes. Calmodulin, a putative target for triarylethylenes, and which is antagonized by 1a, was shown to interact weakly with 7 and 8 and not at all with 3-6. These results suggest that MCF-7 cell growth suppression by 3-8 may be due to interaction with unidentified receptors besides ER and extend earlier findings indicating that events occurring after interaction of these compounds with ER differ from those of triarylethylene antiestrogens.

  DOI：

  10.1021/jm00083a019
• 作为产物：
  描述：

  4-甲氧基-苯甲酸苯酯 在 4-二甲氨基吡啶 、 正丁基锂 、 甲烷磺酸 、 sodium hydride 、 三乙胺 、 乙硫醇 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 4-(3-methoxy-11H-benzofluoren-11-yl)phenol
  参考文献：
  名称：

  Antiestrogens. 3. Estrogen receptor affinities and antiproliferative effects in MCF-7 cells of phenolic analogs of trioxifene, [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl)ethoxy]phenyl[methanone

  摘要：

  Benzothiophenes 3 and 4, derived from the acrylophenone antiestrogen trioxifene (2), are characterized by high estrogen receptor (ER) affinity and low residual estrogenicity compared to tamoxifen (1a). In order to characterize further the growth suppression mechanism for these structural types we have prepared structural variants of 2 bearing hydroxy groups positioned to maximize ER affinity. Thus, dihydronaphthalenes 5 and 6 and benzofluorenes 7 and 8 were prepared and studied in MCF-7 human breast cancer cells, in comparison with 3 and 4. All compounds were powerful suppressants of cell growth, with 50% inhibition ranging from 4.5 to 160 nM. Greatest potency was seen with diphenols 6 and 8. These compounds had intracellular ER affinities ranging from 0.2 to 4.1% of that of estradiol, suggestive of a potential for partial agonist effects. Simultaneous exposure of cells to 0.1-mu-M concentrations of estradiol and 3 or 4 did not affect the degree of growth inhibition seen with 0.1-mu-M 3 or 4 alone. Partial reversal of inhibition occurred when 0.1-mu-M 5-8 were each accompanied by 0.1-mu-M estradiol. Under these conditions complete reversal of growth inhibition has been found with 1a, 1b, and other triarylethylenes. Calmodulin, a putative target for triarylethylenes, and which is antagonized by 1a, was shown to interact weakly with 7 and 8 and not at all with 3-6. These results suggest that MCF-7 cell growth suppression by 3-8 may be due to interaction with unidentified receptors besides ER and extend earlier findings indicating that events occurring after interaction of these compounds with ER differ from those of triarylethylene antiestrogens.

  DOI：

  10.1021/jm00083a019

文献信息

• TfOH-Catalyzed Intramolecular Annulation of 2-(Aryl)-Phenyl-Substituted <i>p</i>-Quinone Methides under Continuous Flow: Total Syntheses of Selaginpulvilin I and Isoselagintamarlin A
  作者：Yogesh A. Pankhade、Rajat Pandey、Shaheen Fatma、Feroz Ahmad、Ramasamy Vijaya Anand

  DOI：10.1021/acs.joc.1c02980

  日期：2022.3.4

  1,6-conjugate arylation of 2-(aryl)-phenyl-substituted p-quinone methides (QMs) under continuous flow using the microreaction technique. This method was found to be very effective for most of the p-QMs, and the corresponding 9-aryl fluorene derivatives were obtained in moderate to excellent yields. Moreover, this protocol was further elaborated to the first total syntheses of selaginpulvilin I and isoselagintamarlin

  在本文中，我们描述了一种通过 TfOH 催化的 2-(芳基)-苯基取代的对醌甲基化物 (QM) 的分子内 1,6-共轭芳基化在连续流动下使用9-芳基芴衍生物的便捷方法。微反应技术。发现该方法对大多数p -QM非常有效，并且以中等至优异的产率获得了相应的 9-芳基芴衍生物。此外，该方案进一步阐述了selaginpulvilin I和isoselagintamarlin A的首次全合成。
• Benzo[a]fluorene compounds
  申请人：Eli Lilly and Company

  公开号：US05147880A1

  公开（公告）日：1992-09-15

  Benzo[a]fluorenes having an aminoalkoxy group on a phenyl ring at the 11-position have estrogenic and anti-estrogenic activity.

  在苯环的11位上带有氨基烷氧基团的苯并[a]芴具有雌激素和抗雌激素活性。
• Benzo(a)fluorene compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP0524742B1

  公开（公告）日：1996-02-28
• US5147880A
  申请人：——

  公开号：US5147880A

  公开（公告）日：1992-09-15