4-fluoro-3-(5-(methoxymethoxy)benzo[d][1,3]dioxol-4-yl)aniline | 1075749-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-fluoro-3-(5-(methoxymethoxy)benzo[d][1,3]dioxol-4-yl)aniline
• CAS: 1075749-58-4
• 化学式: C₁₅H₁₄FNO₄
• 分子量: 291.279
• InChiKey: NWNYEPWSBZKMFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-fluoro-3-(5-(methoxymethoxy)benzo[d][1,3]dioxol-4-yl)aniline 、 邻硝基苯磺酰氯 在 吡啶 作用下， 以100%的产率得到C₂₁H₁₇FN₂O₈S
  参考文献：
  名称：

  Synthesis and SAR study of N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)-arylsulfonamides: Heat shock protein 90 (Hsp90) inhibitors with submicromolar activity in an in vitro assay

  摘要：

  Heat shock protein 90 is emerging as an important target in cancer chemotherapy. In a program directed toward identifying novel chemical probes for Hsp90, we found N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)benzene sulfonamide as an Hsp90 inhibitor with very weak activity. In this report, we present a new and general method for the synthesis of a variety of analogs around this scaffold, and discuss their structure-activity relationships. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.022
• 作为产物：
  描述：

  5-氨基-2-氟苯硼酸 、 4-iodo-5-(methoxymethoxy)-1,3-benzodioxole 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 0.25h， 生成 4-fluoro-3-(5-(methoxymethoxy)benzo[d][1,3]dioxol-4-yl)aniline
  参考文献：
  名称：

  Synthesis and SAR study of N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)-arylsulfonamides: Heat shock protein 90 (Hsp90) inhibitors with submicromolar activity in an in vitro assay

  摘要：

  Heat shock protein 90 is emerging as an important target in cancer chemotherapy. In a program directed toward identifying novel chemical probes for Hsp90, we found N-(4-hydroxy-3-(2-hydroxynaphthalene-1-yl)phenyl)benzene sulfonamide as an Hsp90 inhibitor with very weak activity. In this report, we present a new and general method for the synthesis of a variety of analogs around this scaffold, and discuss their structure-activity relationships. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.022