6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-(piperidin-1-yl)ethylthio)benzoyl]-benzo[b]thiophene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-(piperidin-1-yl)ethylthio)benzoyl]-benzo[b]thiophene
• 英文别名: [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethylsulfanyl)phenyl]methanone
• 化学式: C₂₈H₂₇NO₃S₂
• 分子量: 489.659
• InChiKey: ARJOCRMEGRIBFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(2-Mercaptoethyl)piperidine 在 1,2-二氯乙烯 、 三溴化硼 、 sodium hydride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-hydroxy-2-(4-hydroxyphenyl)-3-[4-(2-(piperidin-1-yl)ethylthio)benzoyl]-benzo[b]thiophene
  参考文献：
  名称：

  Novel nonsteroidal selective estrogen receptor modulators. Carbon and heteroatom replacement of oxygen in the ethoxypiperidine region of raloxifene

  摘要：

  Compounds were synthesized where oxygen in the ethoxypiperidine region of raloxifene is replaced with carbon, sulfur, or nitrogen linkages. Thia- and aza-substituted compounds were prepared by novel methodology. The compounds were evaluated in vitro as selective estrogen receptor modulators (SERMs). Calculations suggested the compounds exhibit an ER-a binding affinity/conformational energy relationship. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00050-5

文献信息

• Substituted benzo(B)thiophene compounds having activity as selective
  申请人：Eli Lilly and Company

  公开号：US05962475A1

  公开（公告）日：1999-10-05

  The present invention provides compounds with nitrogen, sulfur or carbon linked basic side chains of formula ##STR1## where R.sup.1 and R.sup.2 are independently hydrogen, halo, hydroxy, alkoxy, alkylcarbonyloxy, alkoxycarbonyl, alkoxycarbonyloxy, arylcarbonyloxy, aryloxycarbonyloxy, or alkylsulfonyloxy; O--SO.sub.2 --(C.sub.4 -C.sub.6 alkyl), chloro, fluoro, or bromo; W is CHOH, C(O), or CH.sub.2 ; Y is --CH.sub.2 --, --NH--, --NMe--, --S--, --SO.sub.2 --; and R.sup.3 and R.sup.4 are independently hydrogen, alkyl, alkylcarbonyl, alkylamino-carbonyl, or arylcarbonyl, or together with the nitrogen to which they are attached form 1-pyrrolidinyl, 1-piperidinyl, or a 5- or 6-membered imide or cyclic amide ring. The present invention also provides pharmaceutical compositions containing the compounds optionally containing estrogen or progestin, and the use of such compounds, alone, or in combination with estrogen or progestin, for treating osteoporosis, aortal smooth muscle cell proliferation, (particularly restenosis), and estrogen-dependent cancer (particularly breast cancer).

  本发明提供了具有氮、硫或碳链基侧链的化合物，其化学式为##STR1##其中R.sup.1和R.sup.2独立地为氢、卤素、羟基、烷氧基、烷基羧酸酯基、烷氧羧酸酯基、芳基羧酸酯基、芳氧基羧酸酯基、或烷基磺酰氧基；O--SO.sub.2 --（C.sub.4 -C.sub.6烷基）、氯、氟或溴；W为CHOH、C（O）或CH.sub.2；Y为--CH.sub.2 --、--NH--、--NMe--、--S--、--SO.sub.2 --；R.sup.3和R.sup.4独立地为氢、烷基、烷基羧酸酯基、烷基氨基酰基或芳基羧酸酯基，或与它们连接的氮一起形成1-吡咯烷基、1-哌啶基或5-或6-成员环亚胺或环酰胺环。本发明还提供了含有这些化合物的药物组合物，可选含有雌激素或孕激素，并且使用这些化合物，单独或与雌激素或孕激素结合，用于治疗骨质疏松症、主动脉平滑肌细胞增殖（特别是再狭窄）和雌激素依赖性癌症（特别是乳腺癌）。
• Substituted benzo(b)thiophene compounds having activity as selective estrogen receptor modulators
  申请人：ELI LILLY AND COMPANY

  公开号：EP0838464B1

  公开（公告）日：2003-09-10
• US5962475A
  申请人：——

  公开号：US5962475A

  公开（公告）日：1999-10-05
• Novel nonsteroidal selective estrogen receptor modulators. Carbon and heteroatom replacement of oxygen in the ethoxypiperidine region of raloxifene
  作者：Christopher R. Schmid、James P. Sluka、Kristen M. Duke、Andrew W. Glasebrook

  DOI：10.1016/s0960-894x(99)00050-5

  日期：1999.2

  Compounds were synthesized where oxygen in the ethoxypiperidine region of raloxifene is replaced with carbon, sulfur, or nitrogen linkages. Thia- and aza-substituted compounds were prepared by novel methodology. The compounds were evaluated in vitro as selective estrogen receptor modulators (SERMs). Calculations suggested the compounds exhibit an ER-a binding affinity/conformational energy relationship. (C) 1999 Elsevier Science Ltd. All rights reserved.