12-vinyldihydroartemisinyl alcohol | 508234-28-4

• 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-vinyldihydroartemisinyl 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]pent-1-en-3-ol
• CAS: 508234-28-4
• 化学式: C₁₇H₂₈O
• 分子量: 248.409
• InChiKey: YVNMYQVJBMEMHA-IFTGGNMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  12-vinyldihydroartemisinyl alcohol 在 lithium aluminium tetrahydride 、 9-borabicyclo[3.3.1]nonane dimer 、 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 23.5h， 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：

  乙烯基溴化镁 、 dihydroartemisinic aldehyde 以 乙醚 为溶剂， 生成 12-vinyldihydroartemisinyl 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

• A Chiral Pool and Cross Metathesis Based Synthesis of Gingerdiols
  作者：Zhi-Li Wan、Guo-Liang Zhang、Hui-Jun Chen、Yikang Wu、Yan Li

  DOI：10.1002/ejoc.201301727

  日期：2014.4

  Both (3R,5S)- and (3R,5R)-gingerdiols were synthesized. Their 1,3-diol motifs were derived from enantiopure epoxy chiral building blocks that were readily accessible from D-gluconolactone. The effect of deuterating the OH groups of the natural isomer on its optical rotation was also examined. In the course of the syntheses of the targets, an unexplored cross-metathesis (CM) reaction of unprotected

  合成了(3R,5S)-和(3R,5R)-姜二醇。它们的 1,3-二醇基序来源于对映纯环氧手性构件，这些构件很容易从 D-葡萄糖酸内酯中获得。还研究了氘化天然异构体的 OH 基团对其旋光度的影响。在目标的合成过程中，研究了未受保护的 5-取代的 pent-1-ene-3,5-二醇的交叉复分解 (CM) 反应，其中 CM 产物很容易进行烯丙基差向异构化和氧化，因为起始二醇以前所未有的轻松重新排列成酮。这些问题最终通过在苯酚存在下在甲苯中进行 CM 反应得到解决。这些出乎意料但非常有趣的现象的原因，确定是在 5-取代的戊-1-烯-3,5-二醇的 C-5 处存在未保护的 OH 基团。还介绍了机械原理。
• [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
• Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer
  作者：Mankil Jung、Sangmin Lee、Jungyeob Ham、Kyunghoon Lee、Hanjo Kim、Soo Kie Kim

  DOI：10.1021/jm020119d

  日期：2003.3.1

  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.