3-bromo-8-chloro-6-(4-methoxyphenyl)-2-naphthol | 550998-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-bromo-8-chloro-6-(4-methoxyphenyl)-2-naphthol
• 英文别名: 3-bromo-8-chloro-6-(4-methoxyphenyl)naphthalen-2-ol
• CAS: 550998-37-3
• 化学式: C₁₇H₁₂BrClO₂
• 分子量: 363.638
• InChiKey: PENOYHRWRASTMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-8-chloro-6-(4-methoxyphenyl)-2-naphthol 在 N-氯代丁二酰亚胺 、 叔丁基锂 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 1,8-dichloro-6-(4-hydroxyphenyl)-2-naphthol
  参考文献：
  名称：

  ERβ Ligands. 3. Exploiting Two Binding Orientations of the 2-Phenylnaphthalene Scaffold To Achieve ERβ Selectivity

  摘要：

  The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERbeta were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERbeta, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.

  DOI：

  10.1021/jm058173s
• 作为产物：
  描述：

  1-乙酰氨基-7-萘酚 在 咪唑 、 盐酸 、 四(三苯基膦)钯 、 亚硝酸特丁酯 、 四丁基氟化铵 、 溴 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 、 copper dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 18.17h， 生成 3-bromo-8-chloro-6-(4-methoxyphenyl)-2-naphthol
  参考文献：
  名称：

  ERβ Ligands. 3. Exploiting Two Binding Orientations of the 2-Phenylnaphthalene Scaffold To Achieve ERβ Selectivity

  摘要：

  The 2-phenylnaphthalene scaffold was explored as a simplified version of genistein in order to identify ER selective ligands. With the aid of docking studies, positions 1, 4, and 8 of the 2-phenylnaphthalene template were predicted to be the most potentially influential positions to enhance ER selectivity using two different binding orientations. Both orientations have the phenol moiety mimicking the A-ring of genistein. Several compounds predicted to adopt orientations similar to that of genistein when bound to ERbeta were observed to have slightly higher ER affinity and selectivity than genistein. The second orientation we exploited, which was different from that of genistein when bound to ERbeta, resulted in the discovery of several compounds that had superior ER selectivity and affinity versus genistein. X-ray structures of two ER selective compounds (i.e., 15 and 47) confirmed the alternate binding mode and suggested that substituents at positions 1 and 8 were responsible for inducing selectivity. One compound (i.e., 47, WAY-202196) was further examined and found to be effective in two models of inflammation, suggesting that targeting ER may be therapeutically useful in treating certain chronic inflammatory diseases.

  DOI：

  10.1021/jm058173s

文献信息

• Substituted phenyl naphthalenes as estrogenic agents
  申请人：Wyeth

  公开号：US20030181519A1

  公开（公告）日：2003-09-25

  This invention provides estrogen receptor modulators of formula I, having the structure 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 , are as defined in the specification, or a pharmaceutically acceptable salt thereof.

  这项发明提供了具有结构的式I的雌激素受体调节剂 1 其中 R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，R 6 ，R 7 ，R 8 ，R 9 和R 10 如规范中所定义，或其药用可接受盐。
• SUBSTITUTED PHENYL NAPHTHALENES AS ESTROGENIC AGENTS
  申请人：Wyeth

  公开号：EP1453782A2

  公开（公告）日：2004-09-08
• US6914074B2
  申请人：——

  公开号：US6914074B2

  公开（公告）日：2005-07-05
• US7067524B2
  申请人：——

  公开号：US7067524B2

  公开（公告）日：2006-06-27
• [EN] SUBSTITUTED PHENYL NAPHTHALENES AS ESTROGENIC AGENTS<br/>[FR] NAPHTHALENES DE PHENYLE SUBSTITUES EN TANT QU'AGENTS OESTROGENIQUES
  申请人：WYETH CORP

  公开号：WO2003051805A2

  公开（公告）日：2003-06-26

  This invention provides estrogen receptor modulators of formula (I), having the structure (I) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10, are as defined in the specification, or a pharmaceutically acceptable salt thereof.