5-bromo-N-(4-(tert-butyldimethylsilyloxyethyl)phenyl)benzo[d][1,3]dioxole-4-carboxamide | 1079991-20-0

• 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: 5-bromo-N-(4-(tert-butyldimethylsilyloxyethyl)phenyl)benzo[d][1,3]dioxole-4-carboxamide
• 英文别名: 5-bromo-N-[4-[2-[tert-butyl(dimethyl)silyl]oxyethyl]phenyl]-1,3-benzodioxole-4-carboxamide
• CAS: 1079991-20-0
• 化学式: C₂₂H₂₈BrNO₄Si
• 分子量: 478.458
• InChiKey: HQBKBXFVFHYJBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• 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 、 5-bromo-N-(4-(tert-butyldimethylsilyloxyethyl)phenyl)benzo[d][1,3]dioxole-4-carboxamide 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.33h， 以80%的产率得到5-bromo-N-(4-(tert-butyldimethylsilyloxyethyl)phenyl)-N-(methoxymerthyl)benzo[d][1,3]dioxole-4-carboxamide
  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：

  4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)aniline 、 6-bromo-2,3-(methylenedioxy)benzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 5-bromo-N-(4-(tert-butyldimethylsilyloxyethyl)phenyl)benzo[d][1,3]dioxole-4-carboxamide
  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

文献信息

• Structure−Activity Relationship Studies of Phenanthridine-Based Bcl-X_L Inhibitors
  作者：Paul H. Bernardo、Kah-Fei Wan、Thirunavukkarasu Sivaraman、Jin Xu、Felicity K. Moore、Alvin W. Hung、Henry Y. K. Mok、Victor C. Yu、Christina L. L. Chai

  DOI：10.1021/jm8005433

  日期：2008.11.13

  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.