3-[(2-hydroxy-5-nitrophenyl)(morpholino)methyl]-2-methylindole | 511295-38-8

• 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-[(2-hydroxy-5-nitrophenyl)(morpholino)methyl]-2-methylindole
• 英文别名: 2-((2-methyl-1H-indol-3-yl)(morpholino)methyl)-4-nitrophenol；2-methyl-3-[morpholino(2-hydroxy-5-nitrophenyl)methyl]indole；2-[(2-methyl-1H-indol-3-yl)-morpholin-4-ylmethyl]-4-nitrophenol
• CAS: 511295-38-8
• 化学式: C₂₀H₂₁N₃O₄
• 分子量: 367.404
• InChiKey: VYIUXYYLKRKYCY-UHFFFAOYSA-N

物化性质

• 沸点：
  575.8±50.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-[(2-hydroxy-5-nitrophenyl)(morpholino)methyl]-2-methylindole 在 三乙基硅烷 、 水 、 四氯化钛 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 9.55h， 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
• 作为产物：
  描述：

  5-硝基水杨醛 以 异丙醇 为溶剂， 反应 8.0h， 生成 3-[(2-hydroxy-5-nitrophenyl)(morpholino)methyl]-2-methylindole
  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

文献信息

• ——
  作者：L. Yu. Ukhin、L. V. Belousova、Zh. I. Orlova、S. V. Shishkina、O. V. Shishkin

  DOI：10.1023/a:1020956614588

  日期：——

  The reactions of aminals, the Mannich bases, and azomethines derived from substituted salicylaldehydes were studied. Derivatives of tetrahydrocyclopenta[b]- and hexahydro-cyclohepta[b]chromenes and substituted 2,2'-spirobichromenes were prepared from aminals, and substituted hexahydroxanthenes were synthesized from the Mannich bases. Azomethine derivatives of 5-nitrosalicylaldehyde and aliphatic amines react with cyclohexanone to form 4a-amino-7-nitro-2,3,4,4a-tetrahydro-1H-xanthenes. 4a-Morpholino-7-nitro-9-phenylethynyl-1,2,3,4,9,9a-hexahydroxanthene was studied by X-ray diffraction analysis.
• ——
  作者：L. Yu. Ukhin

  DOI：10.1023/a:1023923226389

  日期：——

  Fusion of 2-methylindole with morphinals of substituted salicylaldehydes (in a ratio of 1 : 1) afforded 3-[(2-hydroxyaryl)morpholinomethyl]-2-methylindoles as normal products of the Mannich reaction. In some cases, the reactions with an excess of 2-methylindole resulted in unusual condensation accompanied by the replacement of the OH group by the morpholino group to form bis(2-methylindol-3-yl)(2-morpholinoaryl)methanes.