dimethylaminocustunolide

• 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: dimethylaminocustunolide
• 英文别名: (3R,3aS,6E,10E,11aS)-3-[(dimethylamino)methyl]-6,10-dimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• 化学式: C₁₇H₂₇NO₂
• 分子量: 277.407
• InChiKey: AOYRPYOCOWEJHK-KWKYMYBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  木香烃内酯 、 二甲胺 以 乙醇 为溶剂， 生成 dimethylaminocustunolide
  参考文献：
  名称：

  Synthesis of 13-amino costunolide derivatives as anticancer agents

  摘要：

  A number of costunolide derivatives (4a-p) have been synthesized and evaluated for their in vitro cytotoxicity against eight tumor and a non-tumor cell lines. Compound 4d showed around 2-fold better cytotoxicity against SW-620 (colon) cell line with improved safety index than costunolide (1). While compounds 4e, 4g, and 4p have shown around 2- to 3-fold better cytotoxicity against MIAPaCa2 (pancreas), K-562 (leukemia) and PA-1 (ovary) cell lines as well as better safety index in comparison to costunolide (1). Compound 4p also exhibited cytotoxicity against HBL100 (breast) cell line with 2-fold better safety index. Structure-activity relationship has been described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.083

文献信息

• LiCl-promoted amination of β-methoxy amides (γ-lactones)
  作者：Ru Zhao、Bing-Lin Zeng、Wen-Qiang Jia、Hong-Yi Zhao、Long-Ying Shen、Xiao-Jian Wang、Xian-Dao Pan

  DOI：10.1039/d0ra07170f

  日期：——

  An efficient and mild method has been developed for the amination of β-methoxy amides (γ-lactones) including natural products michelolide, costunolide and parthenolide derivatives by using lithium chloride in good yields. This reaction is applicable to a wide range of substrates with good functional group tolerance. Mechanism studies show that the reactions undergo a LiCl promoted MeOH elimination

  已经开发了一种高效温和的方法，用于以良好收率使用氯化锂胺化 β-甲氧基酰胺（γ-内酯），包括天然产物 michelolide、costunolide 和 parthenolide 衍生物。该反应适用于广泛的具有良好官能团耐受性的底物。机理研究表明，反应经历了 LiCl 促进的 MeOH 从底物中消除形成相应的 α,β-不饱和中间体，然后是胺的迈克尔加成。
• Synthesis of 13-amino costunolide derivatives as anticancer agents
  作者：Sanjay K. Srivastava、Aji Abraham、Beena Bhat、Manu Jaggi、Anu T. Singh、Vinod K. Sanna、Gurvinder Singh、Shiv K. Agarwal、Rama Mukherjee、Anand C. Burman

  DOI：10.1016/j.bmcl.2006.05.083

  日期：2006.8

  A number of costunolide derivatives (4a-p) have been synthesized and evaluated for their in vitro cytotoxicity against eight tumor and a non-tumor cell lines. Compound 4d showed around 2-fold better cytotoxicity against SW-620 (colon) cell line with improved safety index than costunolide (1). While compounds 4e, 4g, and 4p have shown around 2- to 3-fold better cytotoxicity against MIAPaCa2 (pancreas), K-562 (leukemia) and PA-1 (ovary) cell lines as well as better safety index in comparison to costunolide (1). Compound 4p also exhibited cytotoxicity against HBL100 (breast) cell line with 2-fold better safety index. Structure-activity relationship has been described. (c) 2006 Elsevier Ltd. All rights reserved.