(9R,10S)-10-methoxy-3'-(4-chlorophenyl)-spiroisoxazoline

• 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: (9R,10S)-10-methoxy-3'-(4-chlorophenyl)-spiroisoxazoline
• 英文别名: (1R,4S,5R,8S,9R,10S,12R,13R)-3'-(4-chlorophenyl)-10-methoxy-1,5-dimethylspiro[11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane-9,5'-4H-1,2-oxazole]
• 化学式: C₂₃H₂₈ClNO₆
• 分子量: 449.931
• InChiKey: DLNOJZOJEIBCBG-MBUDHKBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  青蒿素	Artemisinin	63968-64-9	C15H22O5	282.337
  ——	artemisitene	101020-89-7	C15H20O5	280.321

反应信息

• 作为产物：
  描述：

  青蒿素 在 sodium tetrahydroborate 、 双氧水 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.5h， 生成 (9R,10S)-10-methoxy-3'-(4-chlorophenyl)-spiroisoxazoline 、 (9R,10R)-10-methoxy-3'-(4-chlorophenyl)-spiroisoxazoline
  参考文献：
  名称：

  Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities

  摘要：

  The sesquiterpene lactone framework of artemisinin was used as a drug repositioning prototype for the development of novel antitumor drugs. Several series of novel artemisinin analogues (artemalogues) were designed and synthesized through 1,3-dipolar cycloaddition of artemisitene with nitrile oxides or nitrones. The isoxazolidine-containing spirobicyclic artemalogue 11b turns out to be the most potent with low micromolar IC50 values against all three tumor cells, which were at least 4- to 14-fold more potent than the parent artemisinin. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.035

文献信息

• 异噁唑琳和异噁唑烷取代的青蒿素衍生物、其 制备方法及应用
  申请人：中国科学院上海药物研究所

  公开号：CN106146537B

  公开（公告）日：2021-03-19

  本发明提供了一种含异噁唑琳和异噁唑烷取代的青蒿素衍生物、其制备方法及应用，具体地，本发明提供了一种如下式I所示的化合物。其中，各基团的定义如说明书中所述。本发明化合物具有肿瘤细胞增殖抑制活性，且可以用于制备肿瘤细胞增殖相关的疾病。
• Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities
  作者：Gang Liu、Shanshan Song、Shiqi Shu、Zehong Miao、Ao Zhang、Chunyong Ding

  DOI：10.1016/j.ejmech.2015.08.035

  日期：2015.10

  The sesquiterpene lactone framework of artemisinin was used as a drug repositioning prototype for the development of novel antitumor drugs. Several series of novel artemisinin analogues (artemalogues) were designed and synthesized through 1,3-dipolar cycloaddition of artemisitene with nitrile oxides or nitrones. The isoxazolidine-containing spirobicyclic artemalogue 11b turns out to be the most potent with low micromolar IC50 values against all three tumor cells, which were at least 4- to 14-fold more potent than the parent artemisinin. (C) 2015 Elsevier Masson SAS. All rights reserved.