3-(10β-dihydroartemisinoxy)propene | 82596-21-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-(10β-dihydroartemisinoxy)propene
• 英文别名: (1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-10-prop-2-enoxy-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• CAS: 82596-21-2
• 化学式: C₁₈H₂₈O₅
• 分子量: 324.417
• InChiKey: QPOKBZWKSVTMNH-QOBNMGNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(10β-dihydroartemisinoxy)propene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Antimalarial Activity of Artemisinin Derivatives Containing an Amino Group

  摘要：

  In search of water-soluble artemisinin derivatives that are more stable than sodium artesunate, over 30 derivatives containing an amino group (compounds 3-5) were synthesized and tested in mice. All products tested (except 5a and 5b) are the beta isomers. These basic compounds combined with organic acids (oxalic acid, maleic acid, etc.) to yield the corresponding salts. Generally, the maleates have better solubility in water than the corresponding oxalates. The aqueous solutions of these salts can be kept at room temperature for several weeks without any discernible decomposition. Compounds 3f, 3h, and 3r are much more active against P. berghei than artesunic acid by oral administration and therefore were further tested in monkeys. However, their oral efficacies are poorer than that of artesunic acid against P. knowlesi in rhesus monkeys. It is interesting to note that 3f, 3h, and 3r showed much lower efficacies against P. berghei when they were administered subcutaneously than orally.

  DOI：

  10.1021/jm990552w
• 作为产物：
  描述：

  dihydroartemisinin 、 烯丙醇 在 三氟化硼乙醚 作用下， 生成 3-(10β-dihydroartemisinoxy)propene
  参考文献：
  名称：

  Synthesis and Antimalarial Activity of Artemisinin Derivatives Containing an Amino Group

  摘要：

  In search of water-soluble artemisinin derivatives that are more stable than sodium artesunate, over 30 derivatives containing an amino group (compounds 3-5) were synthesized and tested in mice. All products tested (except 5a and 5b) are the beta isomers. These basic compounds combined with organic acids (oxalic acid, maleic acid, etc.) to yield the corresponding salts. Generally, the maleates have better solubility in water than the corresponding oxalates. The aqueous solutions of these salts can be kept at room temperature for several weeks without any discernible decomposition. Compounds 3f, 3h, and 3r are much more active against P. berghei than artesunic acid by oral administration and therefore were further tested in monkeys. However, their oral efficacies are poorer than that of artesunic acid against P. knowlesi in rhesus monkeys. It is interesting to note that 3f, 3h, and 3r showed much lower efficacies against P. berghei when they were administered subcutaneously than orally.

  DOI：

  10.1021/jm990552w

文献信息

• 一种青蒿素类衍生物、其合成及应用
  申请人：昆药集团股份有限公司

  公开号：CN107383048B

  公开（公告）日：2019-09-03

  本发明涉及药物合成领域，具体地说，涉及一种青蒿素类衍生物、其合成及应用，更具体地说公开了一类青蒿素类衍生物及其制备方法与在抗肿瘤药物及抗HIV药物中的应用。本发明所述青蒿素类衍生物具有式Ⅰ所示结构，其中，R为其他化合物残基。本发明式Ⅰ所示青蒿素类衍生物的制备方法简单易行，重现性好，环境污染小，可用于式Ⅰ所示化合物的大量制备。本发明所述式Ⅰ所示化合物具有明显的抗肿瘤活性及抗HIV活性。
• New Method for the Synthesis of Ether Derivatives of Artemisinin
  作者：Pranjal P. Bora、Nabajyoti Baruah、Ghanashyam Bez、Nabin C. Barua

  DOI：10.1080/00397911.2010.538887

  日期：2012.4.15

  Dihydroartemisinin can be converted to its ether derivatives in good yields by reaction with different alcohols in the presence of a catalytic amount of dodecatungstophosphoric acid hydrate. Easy handling, trouble-free workup by filtration, excellent yields, and very short reaction times are some of the highlights of this protocol.