1-tert-butyl 2-ethyl 3-benzoyl-5-bromo-1H-indole-1,2-dicarboxylate | 1374964-66-5

• 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: 1-tert-butyl 2-ethyl 3-benzoyl-5-bromo-1H-indole-1,2-dicarboxylate
• CAS: 1374964-66-5
• 化学式: C₂₃H₂₂BrNO₅
• 分子量: 472.335
• InChiKey: PCAXXGPKJYDOFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-tert-butyl 2-ethyl 3-benzoyl-5-bromo-1H-indole-1,2-dicarboxylate 、 methyl triphenylphosphonium bromide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以51%的产率得到1-tert-butyl 2-ethyl 5-bromo-3-(1-phenylvinyl)-1H-indole-1,2-dicarboxylate
  参考文献：
  名称：

  Novel Cyclopropyl-Indole Derivatives as HIV Non-Nucleoside Reverse Transcriptase Inhibitors

  摘要：

  The HIV pandemic represents one of the most serious diseases to face mankind in both a social and economic context, with many developing nations being the worst afflicted. Due to ongoing resistance issues associated with the disease, the design and synthesis of anti-HIV agents presents a constant challenge for medicinal chemists. Utilizing molecular modeling, we have designed a series of novel cyclopropyl indole derivatives as HIV non-nucleoside reverse transcriptase inhibitors and carried out their preparation. These compounds facilitate a double hydrogen bonding interaction to Lys101 and efficiently occupy the hydrophobic pockets in the regions of Tyr181/188 and Val179. Several of these compounds inhibited HIV replication as effectively as nevirapine when tested in a phenotypic assay.

  DOI：

  10.1021/ml3000462
• 作为产物：
  描述：

  5-溴吲哚-2-羧酸乙酯 、 苯甲酰氯 在 4-二甲氨基吡啶 、 aluminum (III) chloride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 生成 1-tert-butyl 2-ethyl 3-benzoyl-5-bromo-1H-indole-1,2-dicarboxylate
  参考文献：
  名称：

  Novel Cyclopropyl-Indole Derivatives as HIV Non-Nucleoside Reverse Transcriptase Inhibitors

  摘要：

  The HIV pandemic represents one of the most serious diseases to face mankind in both a social and economic context, with many developing nations being the worst afflicted. Due to ongoing resistance issues associated with the disease, the design and synthesis of anti-HIV agents presents a constant challenge for medicinal chemists. Utilizing molecular modeling, we have designed a series of novel cyclopropyl indole derivatives as HIV non-nucleoside reverse transcriptase inhibitors and carried out their preparation. These compounds facilitate a double hydrogen bonding interaction to Lys101 and efficiently occupy the hydrophobic pockets in the regions of Tyr181/188 and Val179. Several of these compounds inhibited HIV replication as effectively as nevirapine when tested in a phenotypic assay.

  DOI：

  10.1021/ml3000462