[2-(4-Hydroxy-phenyl)-6-methyl-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(4-Hydroxy-phenyl)-6-methyl-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone
• 英文别名: [2-(4-Hydroxyphenyl)-6-methyl-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
• 化学式: C₂₉H₂₉NO₃S
• 分子量: 471.62
• InChiKey: DGMUKISOCMQSLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-methoxyphenyl)-6-methylbenzo[b]thiophene 在 三氯化铝 、 丙烷-1-硫醇 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 53.0h， 生成 [2-(4-Hydroxy-phenyl)-6-methyl-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-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

• FATTY ACID RALOXIFENE DERIVATIVES AND THEIR USES
  申请人：Milne Jill C.

  公开号：US20110212958A1

  公开（公告）日：2011-09-01

  The invention relates to fatty acid raloxifene derivatives; compositions comprising an effective amount of a fatty acid raloxifene derivative; and methods for treating osteoporosis or preventing invasive breast cancer in postmenopausal women comprising the administration of an effective amount of a fatty acid raloxifene derivative.

  本发明涉及脂肪酸瑞洛珂芬衍生物；包含有效量的脂肪酸瑞洛珂芬衍生物的组合物；以及治疗绝经后妇女骨质疏松症或预防侵袭性乳腺癌的方法，包括给予有效量的脂肪酸瑞洛珂芬衍生物。
• Benzo [b] thiophene compounds, intermediates, formulations, and methods
  申请人：ELI LILLY AND COMPANY

  公开号：EP0835872B1

  公开（公告）日：2006-03-01
• NUCLEOSIDE PHOSPHORAMIDATES AND PHOSPHORAMIDITES
  申请人：Patel Hasmukh B.

  公开号：US20160137685A1

  公开（公告）日：2016-05-19

  The invention provides phosphoramidate prodrugs for targeting and treating liver disease, including liver cancer, hepatocellular carcinoma, and hepatitis.
• LYMPH DIRECTING PRODRUGS
  申请人：Monash University

  公开号：US20170326103A1

  公开（公告）日：2017-11-16

  The present invention relates to compounds and their uses, in particular, compounds in the form of prodrugs that promote transport of a pharmaceutical agent to the lymphatic system and subsequently enhance release of the parent drug.
• US9751852B1
  申请人：——

  公开号：US9751852B1

  公开（公告）日：2017-09-05