7-ethyl-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole | 544705-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 7-ethyl-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole
• CAS: 544705-09-1
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: HRWWZJUFQBPIJR-UHFFFAOYSA-N

物化性质

• 熔点：
  85 °C
• 沸点：
  401.9±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-ethyl-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以98%的产率得到7-ethyl-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol
  参考文献：
  名称：

  Design and Synthesis of Aryl Diphenolic Azoles as Potent and Selective Estrogen Receptor-β Ligands

  摘要：

  New diphenolic azoles as highly selective estrogen receptor-beta agonists are reported. The more potent and selective analogues of these series have comparable binding affinities for ERbeta as the natural ligand 17beta-estradiol but are > 100-fold selective over ERalpha. Our design strategy not only followed a traditional SAR approach but also was supported by X-ray structures of ERbeta cocrystallized with various ligands as well as molecular modeling studies. These strategies enabled us to take advantage of a single conservative residue substitution in the ligand-binding pocket, ERalpha Met(421) --> ERbeta Ile(373), to optimize ERbeta selectivity. The 7-position-substituted benzoxazoles (Table 5) were the most selective ligands of both azole series, with ERB-041 (117) being >200-fold selective for ERbeta. The majority of ERbeta selective agonists tested that were at least similar to50-fold selective displayed a consistent in vivo profile: they were inactive in several models of classic estrogen action (uterotrophic, osteopenia, and vasomotor instability models) and yet were active in the HLA-B27 transgenic rat model of inflammatory bowel disease. These data suggest that ERbeta-selective agonists are devoid of classic estrogenic effects and may offer a novel therapy to treat certain inflammatory conditions.

  DOI：

  10.1021/jm049719y
• 作为产物：
  描述：

  碘乙烷 、 7-溴-5-甲氧基-2-(4-甲氧基苯基)-1,3-苯并恶唑 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以91%的产率得到7-ethyl-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole
  参考文献：
  名称：

  Prodrug substituted benzoxazoles as estrogenic agents

  摘要：

  这项发明提供了具有以下结构的公式I的雌激素受体调节剂，其中Q、Q2、R1、R2、R2a、R3、R3a和X如规范中定义，或其药用可接受盐。

  公开号：

  US20060046968A1

文献信息

• Substituted benzoxazoles as estrogenic agents
  申请人：Wyeth

  公开号：US20030199562A1

  公开（公告）日：2003-10-23

  This invention provides estrogen receptor modulators of formula I, having the structure 1 wherein R 1 , R 2 , R 2a , R 3 , R 3a , and R 4 , and X as defined in the specification, or a pharmaceutically acceptable salt thereof.

  这项发明提供了具有结构1的式I的雌激素受体调节剂，其中R1、R2、R2a、R3、R3a和R4以及规范中定义的X，或其药用可接受盐。
• [EN] SUBSTITUTED BENZOXAZOLES AND ANALOGUES AS ESTROGENIC AGENTS<br/>[FR] BENZOXAZOLES SUBSTITUES ET ANALOGUES UTILISES EN TANT QU'AGENTS OESTROGENES
  申请人：WYETH CORP

  公开号：WO2003050095A1

  公开（公告）日：2003-06-19

  This invention provides estrogen receptor modulators of formula (I), having the structure of formula (I) wherein R1, R2, R2a, R3, R3a, and R4, and X as defined in the specification, or a pharmaceutically acceptable salt thereof.

  本发明提供了公式（I）的雌激素受体调节剂，其具有公式（I）的结构，其中R1、R2、R2a、R3、R3a和R4以及X如规范中定义的，或其药学上可接受的盐。
• PRODRUG SUBSTITUTED BENZOXAZOLES AS ESTROGENIC AGENTS
  申请人：Elmarakby Sayed

  公开号：US20080255057A1

  公开（公告）日：2008-10-16

  This invention provides estrogen receptor modulators of formula I, having the structure wherein Q, Q 2 , R 1 , R 2 , R 2a , R 3 , R 3a , and X as defined in the specification, or a pharmaceutically acceptable salt thereof.

  本发明提供了式I的雌激素受体调节剂，其结构为 其中Q、Q2、R1、R2、R2a、R3、R3a和X如规范中所定义，或其药学上可接受的盐。
• Substituted benzoxazoles and analogues as estrogenic agents
  申请人：Wyeth

  公开号：EP1982713A2

  公开（公告）日：2008-10-22

  This invention provides estrogen receptor modulators of formula I, having the structure wherein R1, R2, R2a, R3, R3a, and R4, and X as defined in the specification, or a pharmaceutically acceptable salt thereof.

  本发明提供了式 I 的雌激素受体调节剂，其结构为 其中 R1、R2、R2a、R3、R3a 和 R4，以及说明书中定义的 X，或其药学上可接受的盐。
• SUBSTITUTED BENZOXAZOLES AND ANALOGUES AS ESTROGENIC AGENTS
  申请人：Wyeth

  公开号：EP1451165A1

  公开（公告）日：2004-09-01