2-(2,3,6-trimethoxy-5-nitrophenyl)ethanol | 884646-69-9

• 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: 2-(2,3,6-trimethoxy-5-nitrophenyl)ethanol
• CAS: 884646-69-9
• 化学式: C₁₁H₁₅NO₆
• 分子量: 257.243
• InChiKey: ZRNDWCAOVIXRON-UHFFFAOYSA-N

物化性质

• 沸点：
  439.6±40.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,3,6-trimethoxy-5-nitrophenyl)ethanol 在 platinum(IV) oxide 偶氮二甲酸二异丙酯 、 氢气 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.0h， 生成 3-amino-2,5,6-trimethoxyphenethyl 5-chloro-2,4-dihydroxybenzoate
  参考文献：
  名称：

  Design, Synthesis, and StructureActivity Relationships for Chimeric Inhibitors of Hsp90

  摘要：

  Inhibition of the 90 kDa heat shock protein (Hsp90) family of molecular chaperones represents a promising new chemotherapeutic approach toward the treatment of several cancers. Previous studies have demonstrated that the natural products, radicicol and geldanamycin, are potent inhibitors of the Hsp90 N-terminal ATP binding site. The cocrystal structures of these molecules bound to Hsp90 have been determined, and through molecular modeling and superimposition of these ligands, hybrids of radicicol and geldanamycin have been designed. A series of macrocylic chimeras of radicicol and geldanamycin and the corresponding seco-agents have been prepared and evaluated for both antiproliferative activity and their ability to induce Hsp90-dependent client protein degradation.

  DOI：

  10.1021/jo061054f
• 作为产物：
  描述：

  1,2,4-三甲氧基苯 在 正丁基锂 、 硝酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 7.5h， 生成 2-(2,3,6-trimethoxy-5-nitrophenyl)ethanol
  参考文献：
  名称：

  Design, Synthesis, and StructureActivity Relationships for Chimeric Inhibitors of Hsp90

  摘要：

  Inhibition of the 90 kDa heat shock protein (Hsp90) family of molecular chaperones represents a promising new chemotherapeutic approach toward the treatment of several cancers. Previous studies have demonstrated that the natural products, radicicol and geldanamycin, are potent inhibitors of the Hsp90 N-terminal ATP binding site. The cocrystal structures of these molecules bound to Hsp90 have been determined, and through molecular modeling and superimposition of these ligands, hybrids of radicicol and geldanamycin have been designed. A series of macrocylic chimeras of radicicol and geldanamycin and the corresponding seco-agents have been prepared and evaluated for both antiproliferative activity and their ability to induce Hsp90-dependent client protein degradation.

  DOI：

  10.1021/jo061054f

文献信息

• Synthesis of a versatile metacyclophane macrolactam
  作者：Mingwen Wang、Brian S.J. Blagg

  DOI：10.1016/j.tetlet.2007.10.150

  日期：2008.1

  geldanamycin and the resorcinol moiety of radicicol, molecules have been produced that are highly effective inhibitors of the Hsp90 protein folding machinery. These chimeric inhibitors contain metacyclophane macrolactams that are difficult to cyclize and modify for incorporation of functional diversity. To circumvent this problem, a highly diversifiable alpha-bromo-alpha,beta-unsaturated ester has

  由于 Hsp90 已成为开发癌症化学治疗剂的有希望的靶点，因此需要对天然产物抑制剂和这种分子伴侣之间的构效关系进行系统评估。利用我们的嵌合体方法，它包含格尔德霉素的醌部分和根癌菌素的间苯二酚部分，已生产出作为 Hsp90 蛋白质折叠机制的高效抑制剂的分子。这些嵌合抑制剂包含难以环化和修饰以纳入功能多样性的间环芳烷大环内酰胺。为了规避这个问题，已经制备了高度多样化的α-溴-α，β-不饱和酯，这允许引入各种功能，从而能够阐明嵌合化合物和 Hsp90 之间的构效关系。本文报道了这种分子的基本原理、合成和优化。
• Heat shock protein 90 inhibitors
  申请人：Blagg Brian

  公开号：US20070197787A1

  公开（公告）日：2007-08-23

  Novel compounds useful for inhibiting the 90 kDa heat shock proteins containing a quinone-like moiety and a di-hydroxy phenol like moiety, similar to geldanamycin and radicicol.
• HEAT SHOCK PROTEIN 90 INHIBITORS
  申请人：Blagg Brian S.J.

  公开号：US20100099865A1

  公开（公告）日：2010-04-22

  Novel compounds useful for inhibiting the 90kDa heat shock proteins containing a quinone-like moiety and a di-hydroxy phenol like moiety, similar to geldanamycin and radicicol.
• US7605288B2
  申请人：——

  公开号：US7605288B2

  公开（公告）日：2009-10-20
• US8188306B2
  申请人：——

  公开号：US8188306B2

  公开（公告）日：2012-05-29