4-Bromo-5-ethoxysampangine | 143858-47-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 1-氮杂氧卟啉
• 英文名称: 4-Bromo-5-ethoxysampangine
• 英文别名: 12-bromo-11-ethoxy-10,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9,11,13(17),14-octaen-8-one
• CAS: 143858-47-3
• 化学式: C₁₇H₁₁BrN₂O₂
• 分子量: 355.191
• InChiKey: RSDAVSSWTOOEEW-UHFFFAOYSA-N

物化性质

• 沸点：
  552.4±50.0 °C(Predicted)
• 密度：
  1.599±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cleistopholine 在 pyridinium hydrobromide perbromide 、 氯化铵 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 25.0h， 生成 4-Bromo-5-ethoxysampangine
  参考文献：
  名称：

  Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines

  摘要：

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.

  DOI：

  10.1021/jm00100a012

文献信息

• Copyrine alkaloids: synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines
  作者：John R. Peterson、Jordan K. Zjawiony、Shihchih Liu、Charles D. Hufford、Alice M. Clark、Robin D. Rogers

  DOI：10.1021/jm00100a012

  日期：1992.10

  Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of the sampangine B-ring at position 4, while the synthesis of A-ring 3-substituted sampangines and benzo[4,5]sampangine (24) were achieved from the corresponding functionalized cleistopholines. Two-dimensional NMR spectroscopy was used to rigorously characterize the A- and B-ring substituent patterns. Structure-activity relationship studies revealed the activity of the sampangines was enhanced by the presence of a substituent at position 3 or by a 4,5-benzo group.