10β-ethyl-10-deoxo-10-dihydroartemisinin

• 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: 10β-ethyl-10-deoxo-10-dihydroartemisinin
• 英文别名: (3R,5aS,6R,8aS,9R,12R,12aR)-10-ethyl-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]-isochromene；(1R,4S,5R,8S,9R,10R,12R,13R)-10-ethyl-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: UPTYPHDYZVEKCN-LTLPSTFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  5.0
• 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

• 作为产物：
  描述：

  dihydroartemisinin 在 三氟化硼乙醚 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.25h， 生成 10β-ethyl-10-deoxo-10-dihydroartemisinin
  参考文献：
  名称：

  Direct conversion of pyranose anomeric OH→F→R in the artemisinin family of antimalarial trioxanes

  摘要：

  Eleven examples form the basis of a short and effective synthetic method for replacement of an anomeric fluorine atom by saturated, unsaturated, aryl and heteroaryl carbon nucleophiles to prepare alpha- or beta-oriented C-10-R derivatives of the trioxane 10-deoxoartemisinin. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00132-4

文献信息

• Synthesis of Qinghaosu Analogues from Dihydroqinghao Aldehyde: A Dark Singlet Oxygen Approach
  作者：Xunshen Liu、Huijun Chen、Zejun Xu、Yikang Wu、Bo Liu

  DOI：10.1002/cjoc.201700055

  日期：2017.4

  A range of qinghaosu (artemisinin) analogues were synthesized from modified dihydroqinghao acid/aldehyde using dark singlet oxygen to trigger off the key step of the trioxane formation. The newly accessed 1,2,4‐trioxanes featured a side chain extended from the carbon corresponding to the lactone carbonyl group of qinghaosu through a stable carbon‐carbon single bond instead of an acetal oxygen‐carbon

  使用暗单线态氧从修饰的二氢青蒿酸/醛合成了一系列的青蒿素（青蒿素）类似物，从而触发了三恶烷形成的关键步骤。新近获得的1,2,4-三恶烷具有一个侧链，该侧链从对应于青蒿素内酯羰基的碳延伸到一个稳定的碳-碳单键，而不是文献中大多数类似物中的乙缩醛-碳键。生物素和各种胺也分别通过这种线性束缚与青蒿素核心相连，以努力开发杂交体和潜在有用的探针以寻找体内靶标。
• Synthesis and Antimalarial Activities of 12.beta.-Allyldeoxoartemisinin and Its Derivatives
  作者：Yu Ming Pu、Herman Ziffer

  DOI：10.1021/jm00004a007

  日期：1995.2

  Synthesis of 12 beta-allyldeoxoartemisinin from dihydroartemisinin and subsequent transformations to other 12 beta-alkyldeoxoartemisinins are described. All compounds were tested in vitro versus two drug-resistant strains (Plasmodium falciparum) of malaria. The in vivo activity and toxicity of the most active compound, 12 beta-propyldeoxoartemisinin, were comparable to that of arteether.

  描述了由二氢青蒿素合成12β-烯丙基脱氧青蒿素和随后转化为其他12β-烷基脱氧青蒿素的方法。所有化合物均在体外与两种疟疾耐药菌株（恶性疟原虫）进行了测试。最活泼的化合物12β-丙基脱氧青蒿素的体内活性和毒性可与Arteether媲美。
• Direct conversion of pyranose anomeric OH→F→R in the artemisinin family of antimalarial trioxanes
  作者：Soon Hyung Woo、Michael H. Parker、Poonsakdi Ploypradith、John Northrop、Gary H. Posner

  DOI：10.1016/s0040-4039(98)00132-4

  日期：1998.3

  Eleven examples form the basis of a short and effective synthetic method for replacement of an anomeric fluorine atom by saturated, unsaturated, aryl and heteroaryl carbon nucleophiles to prepare alpha- or beta-oriented C-10-R derivatives of the trioxane 10-deoxoartemisinin. (C) 1998 Elsevier Science Ltd. All rights reserved.