2-[1-Methylsulfonyl-5-nitro-6-(trifluoromethyl)indol-2-yl]propan-2-ol | 868691-82-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[1-Methylsulfonyl-5-nitro-6-(trifluoromethyl)indol-2-yl]propan-2-ol
• CAS: 868691-82-1
• 化学式: C₁₃H₁₃F₃N₂O₅S
• 分子量: 366.318
• InChiKey: JLIZUUIZBDMFLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-[1-Methylsulfonyl-5-nitro-6-(trifluoromethyl)indol-2-yl]propan-2-ol 在 N-溴代丁二酰亚胺(NBS) 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-[3-bromo-5-nitro-6-(trifluoromethyl)-1H-indol-2-yl]propan-2-ol
  参考文献：
  名称：

  The discovery of a potent orally efficacious indole androgen receptor antagonist through in vivo screening

  摘要：

  A series of novel 2-(1H-indol-2-yl)-propan-2-ols have been designed, synthesized, and screened for their ability to inhibit testosterone-induced prostate weight increases in immature rats. Through the use of this paradigm, we were able to identify compounds that exhibited in vivo potency equal to that of the marketed antiandrogen Casodex (R) when orally administered. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.086
• 作为产物：
  描述：

  5-氨基-2-硝基三氟甲苯 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-[1-Methylsulfonyl-5-nitro-6-(trifluoromethyl)indol-2-yl]propan-2-ol
  参考文献：
  名称：

  The discovery of a potent orally efficacious indole androgen receptor antagonist through in vivo screening

  摘要：

  A series of novel 2-(1H-indol-2-yl)-propan-2-ols have been designed, synthesized, and screened for their ability to inhibit testosterone-induced prostate weight increases in immature rats. Through the use of this paradigm, we were able to identify compounds that exhibited in vivo potency equal to that of the marketed antiandrogen Casodex (R) when orally administered. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.086