<3,4-dihydro-6-hydroxy-2-phenyl-1-naphthalenyl><4-<2-(1-piperidinyl)ethoxy>phenyl>methanone | 138630-65-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: <3,4-dihydro-6-hydroxy-2-phenyl-1-naphthalenyl><4-<2-(1-piperidinyl)ethoxy>phenyl>methanone
• 英文别名: (6-Hydroxy-2-phenyl-3,4-dihydronaphthalen-1-yl)-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
• CAS: 138630-65-6
• 化学式: C₃₀H₃₁NO₃
• 分子量: 453.581
• InChiKey: ADCVYCZOVJNONH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  <3,4-dihydro-6-methoxy-2-phenyl-1-naphthalenyl><4-<2-(1-piperidinyl)ethoxy>phenyl>methanone methanesulfonic acid salt 在 三氯化铝 、 乙硫醇 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以81%的产率得到<3,4-dihydro-6-hydroxy-2-phenyl-1-naphthalenyl><4-<2-(1-piperidinyl)ethoxy>phenyl>methanone
  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