((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-5-yl)methyl cinnamate

• 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: ((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-5-yl)methyl cinnamate
• 英文别名: [(1S,2S,4R,7E,11S)-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-8-yl]methyl (E)-3-phenylprop-2-enoate
• 化学式: C₂₄H₂₆O₅
• 分子量: 394.467
• InChiKey: CEKHWTNKWWCPRP-FNCJUPDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  parthenolide 在 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 selenium(IV) oxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 ((1aR,7aS,10aS,10bS,E)-1a-methyl-8-methylene-9-oxo-1a,2,3,6,7,7a,8,9,10a,10b-decahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-5-yl)methyl cinnamate
  参考文献：
  名称：

  倍半萜内酯—肉桂酸衍生物及其盐，药物组合物及其用途

  摘要：

  本发明提供了式(I)倍半萜内酯‑肉桂酸衍生物及其盐在制备治疗癌症的药物和在制备治疗癌症的辅助药物中的用途。

  公开号：

  CN111454275B

文献信息

• Design and synthesis of parthenolide-SAHA hybrids for intervention of drug-resistant acute myeloid leukemia
  作者：Weizhi Ge、Zhongquan Liu、Yu Sun、Tianpeng Wang、Hongyu Guo、Xinyi Chen、Shengzu Li、Mengmeng Wang、Yue Chen、Yahui Ding、Quan Zhang

  DOI：10.1016/j.bioorg.2019.03.056

  日期：2019.6

  A series of parthenolide-SAHA hybrids were synthesized and evaluated for their anti-AML activities against HL-60 and HL-60/ADR cell lines. The most active compound 26 exhibited high activity against HL-60/ADR cell line with IC50 value of 0.15 mu M, which demonstrated 16.8-fold improvement compared to that of the parent compound PTL (IC50, = 2.52 mu M). Moreover, it was six times more potent than the reference drug SAHA (IC50 = 0.90 mu M) and fifty-one times more potent than ADR (IC50 , = 7.72 mu M). The preliminary molecular mechanism of 26 indicated that compound 26 could significantly induce apoptosis of HL-60/ADR cells. The effect of compound 26 was mainly through mitochondria pathway. Further investigation revealed that the protein level of HDAC1 and HDAC6 were reduced after the treatment of compound 26 with a dose-dependent manner. Compound 26 could significantly decrease ABCC1 expression, which increased the accumulation of intracellular drug for overcoming the drug resistance. On the base of these results, compound 26 might be considered as a promising candidate for further evaluation as a potential anti-AML drug.
• 倍半萜内酯—肉桂酸衍生物及其盐，药物组合物及其用途
  申请人：洛阳尚德药缘科技有限公司

  公开号：CN111454275B

  公开（公告）日：2023-07-14

  本发明提供了式(I)倍半萜内酯‑肉桂酸衍生物及其盐在制备治疗癌症的药物和在制备治疗癌症的辅助药物中的用途。