2-bromo-N-(4-(tert-butyldimethylsilyloxymethyl)phenyl)-5,6-dimethoxybenzamide | 1079991-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-N-(4-(tert-butyldimethylsilyloxymethyl)phenyl)-5,6-dimethoxybenzamide
• 英文别名: 6-bromo-N-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-2,3-dimethoxybenzamide
• CAS: 1079991-17-5
• 化学式: C₂₂H₃₀BrNO₄Si
• 分子量: 480.474
• InChiKey: HPQZSGYKMZJIMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴甲基甲基醚 、 2-bromo-N-(4-(tert-butyldimethylsilyloxymethyl)phenyl)-5,6-dimethoxybenzamide 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.33h， 以90%的产率得到2-bromo-N-(4-(tert-butyldimethylsilyloxymethyl)phenyl)-N-(methoxymerthyl)-5,6-dimethoxybenzamide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

  摘要：

  Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-X-L protein. This paper details the synthesis of phenanthridine-based analogues of the natural products that were used to probe this difference in binding profiles. The inhibitory constants for these compounds were then measured in a fluorescence polarization assay against Bcl-X-L. and the tagged Bak-BH3 peptide. The results led to structure-activity relationship studies, which identified the structural motifs required for binding-site specificity as well as inhibitory activity. We also identified synthetic analogues of the natural products that display similar binding modes but with more potent IC50 values.

  DOI：

  10.1021/jm8005433
• 作为产物：
  描述：

  6-bromo-2,3-dimethoxybenzoyl chloride 、 4-[[[(1,1-二甲基乙基)二甲基硅烷基]氧基]甲基]苯胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以2.24 g的产率得到2-bromo-N-(4-(tert-butyldimethylsilyloxymethyl)phenyl)-5,6-dimethoxybenzamide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors

  摘要：

  Despite their structural similarities, the natural products chelerythrine (5) and sanguinarine (6) target different binding sites on the pro-survival Bcl-X-L protein. This paper details the synthesis of phenanthridine-based analogues of the natural products that were used to probe this difference in binding profiles. The inhibitory constants for these compounds were then measured in a fluorescence polarization assay against Bcl-X-L. and the tagged Bak-BH3 peptide. The results led to structure-activity relationship studies, which identified the structural motifs required for binding-site specificity as well as inhibitory activity. We also identified synthetic analogues of the natural products that display similar binding modes but with more potent IC50 values.

  DOI：

  10.1021/jm8005433