10-α-ethanethiodihydroartemisinin | 133160-60-8

• 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-α-ethanethiodihydroartemisinin
• 英文别名: (1R,4S,5R,8S,9R,10S,12S,13R)-10-ethylsulfanyl-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• CAS: 133160-60-8
• 化学式: C₁₇H₂₈O₄S
• 分子量: 328.473
• InChiKey: LSTVIQWGCBMICO-XQLAAWPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10-α-ethanethiodihydroartemisinin 在 aluminum oxide 、 氢氧化钾 、 二溴二氟甲烷 、 urea hydrogen peroxide 、 碳酸氢钠 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 乙腈 、 叔丁醇 为溶剂， 反应 1.58h， 生成 (E)-10-(1-bromoethylidene)deoxoartemisinin
  参考文献：
  名称：

  Efficient Synthesis of exo-Olefinated Deoxoartemisinin Derivatives by Ramberg−Bäcklund Rearrangement

  摘要：

  10-exo-Bromoalkylidene- and benzylidenedeoxoartemisinins were synthesized from corresponding 10-alkane-sulfonyldihydroartemisinin and 10-phenylmethanesulfonyldihydroartemisinin using a highly efficient, mild, and simple Ramberg-Backlund rearrangement.

  DOI：

  10.1021/jo035505x
• 作为产物：
  描述：

  dihydroartemisinin 、 乙硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到10-α-ethanethiodihydroartemisinin
  参考文献：
  名称：

  Efficient Synthesis of exo-Olefinated Deoxoartemisinin Derivatives by Ramberg−Bäcklund Rearrangement

  摘要：

  10-exo-Bromoalkylidene- and benzylidenedeoxoartemisinins were synthesized from corresponding 10-alkane-sulfonyldihydroartemisinin and 10-phenylmethanesulfonyldihydroartemisinin using a highly efficient, mild, and simple Ramberg-Backlund rearrangement.

  DOI：

  10.1021/jo035505x

文献信息

• Synthesis of Artemisinins with Substituted Sulfidyl or Sulfonyl Moiety and Their Anti-angiogenesis Activity
  作者：Sang-Tae Oh、Woon-Seob Shin、Jung-Yeob Ham、Seok-Joon Lee

  DOI：10.5012/bkcs.2011.32.8.2823

  日期：2011.8.20
• Synthesis and antiangiogenic activity of exo -olefinated deoxoartemisinin derivatives
  作者：Sangtae Oh、In Howa Jeong、Woon-Seob Shin、Seokjoon Lee

  DOI：10.1016/j.bmcl.2004.05.013

  日期：2004.7

  10-exo-Bromoalkylidene and benzylidene deoxoarternisinin derivatives with antiangiogenic activity were synthesized from corresponding 10-alkanesulfonyl dihydroartemisinin and 10-phenylmethanesulfonyl dihydroartemisinin using a highly efficient, mild, and simple Ramberg-Backlund rearrangement. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.
• Efficient Synthesis of <i>e</i><i>xo</i>-Olefinated Deoxoartemisinin Derivatives by Ramberg−Bäcklund Rearrangement
  作者：Sangtae Oh、In Howa Jeong、Seokjoon Lee

  DOI：10.1021/jo035505x

  日期：2004.2.1

  10-exo-Bromoalkylidene- and benzylidenedeoxoartemisinins were synthesized from corresponding 10-alkane-sulfonyldihydroartemisinin and 10-phenylmethanesulfonyldihydroartemisinin using a highly efficient, mild, and simple Ramberg-Backlund rearrangement.