12-(2'-hydroxyethyl)dihydroartemisinyl alcohol | 508234-29-5

• 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: 12-(2'-hydroxyethyl)dihydroartemisinyl alcohol
• 英文别名: (3R,4R)-4-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]pentane-1,3-diol
• CAS: 508234-29-5
• 化学式: C₁₇H₃₀O₂
• 分子量: 266.424
• InChiKey: LTCHCDWVAXHIIK-IFTGGNMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-(2'-hydroxyethyl)dihydroartemisinyl alcohol 在 lithium aluminium tetrahydride 、 sodium azide 、 氧气 、 rose bengal 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.0h， 生成 12-(2'-aminoethyl)deoxoartemisinin
  参考文献：
  名称：

  Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer

  摘要：

  The first primary amines 9 and bromoalkyl analogues 7 of deoxoartemisinin with nonacetal functionality at C-12 are prepared as versatile intermediates for the synthesis of various derivatives. Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Dimers, particularly 12a, 18a,b, and trimer 17, were especially potent and selective at inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. The linker with one amide- or one sulfur-centered two ethylene groups of the dimers is essential for high anticancer activity. Trimer 17 shows very potent activity against most of the human cancer cell lines tested.

  DOI：

  10.1021/jm020119d
• 作为产物：
  描述：

  dihydroartemisinic aldehyde 在 9-borabicyclo[3.3.1]nonane dimer 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.5h， 生成 12-(2'-hydroxyethyl)dihydroartemisinyl alcohol
  参考文献：
  名称：

  Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer

  摘要：

  The first primary amines 9 and bromoalkyl analogues 7 of deoxoartemisinin with nonacetal functionality at C-12 are prepared as versatile intermediates for the synthesis of various derivatives. Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Dimers, particularly 12a, 18a,b, and trimer 17, were especially potent and selective at inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. The linker with one amide- or one sulfur-centered two ethylene groups of the dimers is essential for high anticancer activity. Trimer 17 shows very potent activity against most of the human cancer cell lines tested.

  DOI：

  10.1021/jm020119d

文献信息

• [EN] DEOXOARTEMISININ ANALOGS, PROCESS FOR THEIR PREPARATION, AND ANTICANCER AGENT COMPRISING THEM<br/>[FR] ANALOGUES DE DEOXOARTEMISININE ET LEURS PROCEDE DE PREPARATION, ET AGENT ANTICANCER LES RENFERMANT
  申请人：JUNG MAN-KIL

  公开号：WO2004078762A1

  公开（公告）日：2004-09-16

  The present invention relates to a new deoxoartemisinin dimer and trimer, which have excellent anticancer activity and lower toxicity and are stable to acids, to a new deoxoartemisinin monomer of intermediate thereof, to preparations thereof, and to anticancer agents comprising the deoxoartemisinin dimer or trimer.

  本发明涉及一种新的脱氧青蒿素二聚体和三聚体，具有优异的抗癌活性和较低的毒性，并且对酸稳定，涉及一种新的脱氧青蒿素单体或其中间体，以及其制备和包含脱氧青蒿素二聚体或三聚体的抗癌剂。
• US7205332B2
  申请人：——

  公开号：US7205332B2

  公开（公告）日：2007-04-17