1-(4-methoxyphenyl)-2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1-(6-methoxynaphthalen-2-yl)propene | 848073-47-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-methoxyphenyl)-2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1-(6-methoxynaphthalen-2-yl)propene
• CAS: 848073-47-2
• 化学式: C₃₄H₃₇NO₃
• 分子量: 507.673
• InChiKey: IMQAONNPPIKDFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  30.93
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1-(6-methoxynaphthalen-2-yl)propene 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以73%的产率得到1-(4-hydroxyphenyl)-2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1-(6-hydroxynaphthalen-2-yl)propene
  参考文献：
  名称：

  In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆

  摘要：

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.051
• 作为产物：
  描述：

  2-溴-6-甲氧基萘 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 环己烷 为溶剂， 反应 2.08h， 生成 1-(4-methoxyphenyl)-2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1-(6-methoxynaphthalen-2-yl)propene
  参考文献：
  名称：

  In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆

  摘要：

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.051