[2-(3-methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone | 185416-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(3-methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone
• 英文别名: [2-(3-Methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone；[6-methoxy-2-(4-methoxy-3-methylphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
• CAS: 185416-32-4
• 化学式: C₃₁H₃₃NO₄S
• 分子量: 515.673
• InChiKey: FCWWFLBOAHXZCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-(3-methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone 在 三氯化铝 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 以386 mg (64%)的产率得到[2-(3-Methyl-4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone
  参考文献：
  名称：

  Benzo [B] thiophene compounds, and compositions for treating bone loss,

  摘要：

  这项发明提供了苯并[b]噻吩化合物、配方和抑制骨质流失或骨吸收的方法，特别是针对骨质疏松症和与心血管相关的病理条件，包括高脂血症和相关的心血管病理条件。

  公开号：

  US05998442A1
• 作为产物：
  描述：

  6-甲氧基-N,N-二甲基苯并[b]噻吩-2-胺 以 四氢呋喃 、 氯苯 为溶剂， 反应 10.5h， 生成 [2-(3-methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]phenyl]methanone
  参考文献：
  名称：

  Structure−Activity Relationships of Selective Estrogen Receptor Modulators:  Modifications to the 2-Arylbenzothiophene Core of Raloxifene

  摘要：

  The 8-arylbenzothiophene raloxifene, 1, is a selective estrogen receptor modulator which is currently under clinical evaluation for the prevention and treatment of postmenopausal osteoporosis. A series of raloxifene analogs which contain modifications to the 2-arylbenzothiophene core have been prepared and evaluated for the ability to bind to the estrogen receptor and inhibit MCF-7 breast cancer cell proliferation in vitro. Their ability to function as tissue-selective estrogen agonists in vivo has been assayed in a short-term, ovariectomized (OVX) rat model with end points of serum cholesterol lowering, uterine weight gain, and uterine eosinophil peroxidase activity. These studies have demonstrated that (1) the 6-hydroxy and, to a lesser extent, the 4'-hydroxy substituents of raloxifene are important for receptor binding and in vitro activity, (2) small, highly electronegative 4'-substituents such as hydroxy, fluoro, and chloro are preferred both in vitro and in vivo, (3) increased steric bulk at the 4'-position leads to increased uterine stimulation in, vivo, and (4) additional substitution of the 2-aryl moiety is tolerated while additional substitution at the 4-, 5-, or 7-position of the benzothiophene results in reduced biological activity. In addition, compounds in which the 2-aryl group is replaced by alkyl, cycloalkyl, and naphthyl substituents maintain a profile of in vitro and in vivo biological activity qualitatively similar to that of raloxifene. Several novel structural variants including 2-cyclohexyl, 2-naphthyl, and 6-carbomethoxy analogs also demonstrated efficacy in preventing bone loss in a chronic OVX rat model of postmenopausal osteopenia, at doses of 0.1-10 mg/kg.

  DOI：

  10.1021/jm9606352

文献信息

• Benzo[b]thiophene compounds, intermediates, processes, compositions and methods
  申请人：Eli Lilly & Company

  公开号：EP1493741A2

  公开（公告）日：2005-01-05

  The invention provides benzo[b]thiophene compounds, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, and cardiovascular-related pathological conditions including hyperlipidemia and related cardiovascular pathologies.

  本发明提供了苯并[b]噻吩化合物、制剂和抑制骨质流失或骨吸收（尤其是骨质疏松症）以及心血管相关病症（包括高脂血症和相关心血管病症）的方法。
• Benzo[B]thiophene compounds, intermediates, processes, compositions, and methods
  申请人：ELI LILLY AND COMPANY

  公开号：EP0826683B1

  公开（公告）日：2004-10-06
• US5998442A
  申请人：——

  公开号：US5998442A

  公开（公告）日：1999-12-07