3-(4-t-butylphenyl)-3-hydroxy-2-propyl-2,3-dihydroisoindol-1-one | 915975-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-(4-t-butylphenyl)-3-hydroxy-2-propyl-2,3-dihydroisoindol-1-one
• 英文别名: 3-(4-Tert-butylphenyl)-3-hydroxy-2-propylisoindol-1-one
• CAS: 915975-25-6
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: UAEOFQKFWMHSQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-t-butylphenyl)-3-hydroxy-2-propyl-2,3-dihydroisoindol-1-one 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 3-(4-tert-butylphenyl)-3-[2-(4-hydroxyphenyl)ethoxy]-2-propyl-2,3-dihydroisoindol-1-one
  参考文献：
  名称：

  Small-Molecule Inhibitors of the MDM2-p53 Protein−Protein Interaction Based on an Isoindolinone Scaffold

  摘要：

  From a set of weakly potent lead compounds, using in silico screening and small library synthesis, a series of 2-alkyl-3-aryl-3-alkoxyisoindolinones has been identified as inhibitors of the MDM2-p53 interaction. Two of the most potent compounds, 2-benzyl-3-(4-chlorophenyl)-3-(3-hydroxypropoxy)-2,3-dihydroisoindol-1-one (76; IC50 = 15.9 +/- 0.8 mu M) and 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2,3-dihydroisoindol-1-one (79; IC50) 5.3 (0.9 mu M), induced p53-dependent gene transcription, in a dose-dependent manner, in the MDM2 amplified, SJSA human sarcoma cell line.

  DOI：

  10.1021/jm0601194
• 作为产物：
  描述：

  N-丙基苯甲酰胺 、 4-叔丁基苯甲酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.6h， 以84%的产率得到3-(4-t-butylphenyl)-3-hydroxy-2-propyl-2,3-dihydroisoindol-1-one
  参考文献：
  名称：

  Small-Molecule Inhibitors of the MDM2-p53 Protein−Protein Interaction Based on an Isoindolinone Scaffold

  摘要：

  From a set of weakly potent lead compounds, using in silico screening and small library synthesis, a series of 2-alkyl-3-aryl-3-alkoxyisoindolinones has been identified as inhibitors of the MDM2-p53 interaction. Two of the most potent compounds, 2-benzyl-3-(4-chlorophenyl)-3-(3-hydroxypropoxy)-2,3-dihydroisoindol-1-one (76; IC50 = 15.9 +/- 0.8 mu M) and 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2,3-dihydroisoindol-1-one (79; IC50) 5.3 (0.9 mu M), induced p53-dependent gene transcription, in a dose-dependent manner, in the MDM2 amplified, SJSA human sarcoma cell line.

  DOI：

  10.1021/jm0601194

文献信息

• Small-Molecule Inhibitors of the MDM2-p53 Protein−Protein Interaction Based on an Isoindolinone Scaffold
  作者：Ian R. Hardcastle、Shafiq U. Ahmed、Helen Atkins、Gillian Farnie、Bernard T. Golding、Roger J. Griffin、Sabrina Guyenne、Claire Hutton、Per Källblad、Stuart J. Kemp、Martin S. Kitching、David R. Newell、Stefano Norbedo、Julian S. Northen、Rebecca J. Reid、K. Saravanan、Henriëtte M. G. Willems、John Lunec

  DOI：10.1021/jm0601194

  日期：2006.10.1

  From a set of weakly potent lead compounds, using in silico screening and small library synthesis, a series of 2-alkyl-3-aryl-3-alkoxyisoindolinones has been identified as inhibitors of the MDM2-p53 interaction. Two of the most potent compounds, 2-benzyl-3-(4-chlorophenyl)-3-(3-hydroxypropoxy)-2,3-dihydroisoindol-1-one (76; IC50 = 15.9 +/- 0.8 mu M) and 3-(4-chlorophenyl)-3-(4-hydroxy-3,5-dimethoxybenzyloxy)-2-propyl-2,3-dihydroisoindol-1-one (79; IC50) 5.3 (0.9 mu M), induced p53-dependent gene transcription, in a dose-dependent manner, in the MDM2 amplified, SJSA human sarcoma cell line.