3-(4a-allyl-7-nitro-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)-2-methyl-1H-indole | 1611471-14-7

• 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: 3-(4a-allyl-7-nitro-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)-2-methyl-1H-indole
• CAS: 1611471-14-7
• 化学式: C₂₅H₂₆N₂O₃
• 分子量: 402.493
• InChiKey: FCGHQHZADWFPJE-UHFFFAOYSA-N

物化性质

• 沸点：
  562.7±50.0 °C(predicted)
• 密度：
  1.227±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  68.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4a-allyl-7-nitro-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)-2-methyl-1H-indole 在 4-二甲氨基吡啶 、 臭氧 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.83h， 生成 2-(9-(2-methyl-1H-indol-3-yl)-7-nitro-2,3,4,4a,9,9a-hexahydro-1H-xanthen-4a-yl)acetaldehyde
  参考文献：
  名称：

  The hit-to-lead optimization of 1,2,3,4,4a,9a-hexahydro-1H-xanthenes as glucocorticoid receptor antagonists

  摘要：

  The structure activity relationship (SAR) study of a 1,2,3,4,4a,9a-hexahydro-1H-xanthene series of selective, human glucocorticoid receptor alpha (hGR alpha) antagonists is reported. Compounds were screened using hydroxyapatite-based GR binding and MMTV-Luc co-transfection reporter gene assays. Four different regions of the scaffold were modified to assess the effects on hGRa antagonism and related potency. Compound 8d exhibits an 8-fold better bioactivity than the original hit 1a, as well as an improved chemical stability, which make it a promising lead for the subsequent optimization. (C) 2014 Ming-Wei Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.017
• 作为产物：
  描述：

  环己酮 在 三乙基硅烷 、 水 、 四氯化钛 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.55h， 生成 3-(4a-allyl-7-nitro-2,3,4,4a,9,9a-hexahydro-1H-xanthen-9-yl)-2-methyl-1H-indole
  参考文献：
  名称：

  The hit-to-lead optimization of 1,2,3,4,4a,9a-hexahydro-1H-xanthenes as glucocorticoid receptor antagonists

  摘要：

  The structure activity relationship (SAR) study of a 1,2,3,4,4a,9a-hexahydro-1H-xanthene series of selective, human glucocorticoid receptor alpha (hGR alpha) antagonists is reported. Compounds were screened using hydroxyapatite-based GR binding and MMTV-Luc co-transfection reporter gene assays. Four different regions of the scaffold were modified to assess the effects on hGRa antagonism and related potency. Compound 8d exhibits an 8-fold better bioactivity than the original hit 1a, as well as an improved chemical stability, which make it a promising lead for the subsequent optimization. (C) 2014 Ming-Wei Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.017