10-乙氧基-1,5,9-三甲基-11,14,15-三氧杂四环[10.2.1.04,13.08,13]十五烷 | 112297-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 中文名称: 10-乙氧基-1,5,9-三甲基-11,14,15-三氧杂四环[10.2.1.04,13.08,13]十五烷
• 英文名称: deoxyarteether
• 英文别名: Deoxy Arteether；(1S,4S,5R,8S,9R,10S,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15-trioxatetracyclo[10.2.1.04,13.08,13]pentadecane
• CAS: 112297-79-7
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: QNIBYSJOIWYARP-XQLAAWPRSA-N

物化性质

• 熔点：
  68-70?C
• 溶解度：
  DMSO（微溶，加热）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-乙氧基-1,5,9-三甲基-11,14,15-三氧杂四环[10.2.1.04,13.08,13]十五烷 在 acid catalyst 作用下， 以 氘代氯仿 为溶剂， 生成 anhydrodeoxydihydroartemisinin
  参考文献：
  名称：

  Gerpe, Lourdes Dominguez; Yeh, Herman J.C.; Yu, Qian-Sheng, Heterocycles, 1988, vol. 27, # 4, p. 897 - 901

  摘要：

  DOI：
• 作为产物：
  描述：

  双氢青蒿素 在 Lindlar's catalyst 三氟化硼乙醚 、 氢气 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.0h， 生成 10-乙氧基-1,5,9-三甲基-11,14,15-三氧杂四环[10.2.1.04,13.08,13]十五烷
  参考文献：
  名称：

  Arteether, a new antimalarial drug: synthesis and antimalarial properties

  摘要：

  Arteether (6) has been prepared from dihydroquinghaosu (3) by etherification with ethanol in the presence of Lewis acid and separated from its chromatographically slower moving alpha-dihydroqinghaosu ethyl ether (7). The absolute stereochemistry at C-12 has been determined by 1H NMR data (J11,12, NOESY). Ethyl ethers 6 and 7 showed potent in vitro inhibition of Plasmodium falciparum, and both compounds were highly potent antimalarials in mice infected with a drug-sensitive strain of Plasmodium berghei. Crystalline arteether (6) and its oily epimer 7 were 2-3 times more potent schizontocides than quinghaosu (1), but deoxy compounds 8, 9, and 11 were 100-300 times less potent in vitro than their corresponding peroxy precursors. Pharmacological studies have shown arteether(6) to have antimalarial activity in animals comparable to artesunate (2) and artemether (4), both of which are fast-acting blood schizontocides in humans. Arteether (6) has now been chosen for a clinical evaluation in high-risk malaria patients.

  DOI：

  10.1021/jm00398a026

文献信息

• Arteether, a new antimalarial drug: synthesis and antimalarial properties
  作者：A. Brossi、B. Venugopalan、L. Dominguez Gerpe、H. J. C. Yeh、J. L. Flippen-Anderson、P. Buchs、X. D. Luo、W. Milhous、W. Peters

  DOI：10.1021/jm00398a026

  日期：1988.3

  Arteether (6) has been prepared from dihydroquinghaosu (3) by etherification with ethanol in the presence of Lewis acid and separated from its chromatographically slower moving alpha-dihydroqinghaosu ethyl ether (7). The absolute stereochemistry at C-12 has been determined by 1H NMR data (J11,12, NOESY). Ethyl ethers 6 and 7 showed potent in vitro inhibition of Plasmodium falciparum, and both compounds were highly potent antimalarials in mice infected with a drug-sensitive strain of Plasmodium berghei. Crystalline arteether (6) and its oily epimer 7 were 2-3 times more potent schizontocides than quinghaosu (1), but deoxy compounds 8, 9, and 11 were 100-300 times less potent in vitro than their corresponding peroxy precursors. Pharmacological studies have shown arteether(6) to have antimalarial activity in animals comparable to artesunate (2) and artemether (4), both of which are fast-acting blood schizontocides in humans. Arteether (6) has now been chosen for a clinical evaluation in high-risk malaria patients.
• Gerpe, Lourdes Dominguez; Yeh, Herman J.C.; Yu, Qian-Sheng, Heterocycles, 1988, vol. 27, # 4, p. 897 - 901
  作者：Gerpe, Lourdes Dominguez、Yeh, Herman J.C.、Yu, Qian-Sheng、Brossi, Arnold、Flippen-Anderson, Judith L.

  DOI：——

  日期：——