10-β-<(2,3-oxopropan-1)-oxy>dihydroartemisinin | 390800-45-0

• 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: 10-β-<(2,3-oxopropan-1)-oxy>dihydroartemisinin
• 英文别名: 3-(10β-dihydroartemisinoxy)-1,2-oxopropane；(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-10-(oxiran-2-ylmethoxy)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• CAS: 390800-45-0
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: DSZCAJXOORFAFE-KPRAYAHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  异丙胺 、 10-β-<(2,3-oxopropan-1)-oxy>dihydroartemisinin 以 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 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 10-β-<(2,3-oxopropan-1)-oxy>dihydroartemisinin
  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

• Antimalarial activity of new ethers and thioethers of dihydroartemisinin
  作者：B Venugopalan、PJ Karnik、CP Bapat、DK Chatterjee、N Iyer、D Lepcha

  DOI：10.1016/0223-5234(96)88287-0

  日期：1995.1

  Various ethers and thioethers of dihydroartemisinin were prepared by treating dihydroartemisinin with hydroxy alkyl, substituted phenol, hydroxy aralkyl, hydroxy alkynyl and hydroxy heteroalkyl or thiols in the presence of BF(3)Et(2)O. The thioethers 64 and 65 were further oxidised to the respective sulfoxides. These derivatives were tested in the Plasmodium berghei K-173-infected mice and some active compounds were tested in chloroquine-resistant P yoelii nigeriensis (NS)-infected mice. Initially the compounds were administered subcutaneously and subsequently by the oral route. The antimalarial activity of the compounds 22, 23, 36, 66 and 79 were found to be comparable to that of arteether when tested in the K-173-infected mice. These compounds also showed activity in the P y nigeriensis (NS)-infected mice.
• Synthesis and Antimalarial Activity of Artemisinin Derivatives Containing an Amino Group
  作者：Ying Li、Yuan-Ming Zhu、Hong-Jian Jiang、Jian-Ping Pan、Guang-Shao Wu、Jin-Ming Wu、Yun-Lin Shi、Jun-De Yang、Bo-An Wu

  DOI：10.1021/jm990552w

  日期：2000.4.1

  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.