acetone O-[5-methoxy-2-(4-methoxy-2,5-dipropylbenzoyl)phenyl]oxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: acetone O-[5-methoxy-2-(4-methoxy-2,5-dipropylbenzoyl)phenyl]oxime
• 英文别名: (4-methoxy-2,5-dipropylphenyl)-[4-methoxy-2-(propan-2-ylideneamino)oxyphenyl]methanone
• 化学式: C₂₄H₃₁NO₄
• 分子量: 397.514
• InChiKey: SYMIJTYPDMSKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acetone O-[5-methoxy-2-(4-methoxy-2,5-dipropylbenzoyl)phenyl]oxime 在 乙腈 、 silica gel 作用下， 以 乙腈 、 盐酸 为溶剂， 反应 4.0h， 以Flash chromatography with silica gel (gradient to 8% EtOAc/hexanes) provided the title compound as a colorless oil (1.72 g, 87% yield for two steps)的产率得到6-methoxy-3-(4-methoxy-2,5-dipropylphenyl)-1,2-benzisoxazole
  参考文献：
  名称：

  Phenyl benzisoxazoles as estrogenic agents

  摘要：

  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和R3如规范中所定义，或其药学上可接受的盐。

  公开号：

  US06884814B2
• 作为产物：
  描述：

  1-(甲氧基甲氧基)-3-丙基苯 在 三乙基硅烷 、 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 potassium tert-butylate 、 叔丁基锂 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 、 正戊烷 为溶剂， 反应 64.5h， 生成 acetone O-[5-methoxy-2-(4-methoxy-2,5-dipropylbenzoyl)phenyl]oxime
  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

文献信息

• US6884814B2
  申请人：——

  公开号：US6884814B2

  公开（公告）日：2005-04-26