N-butyl-5-(3-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yloxy)-N-methylpentanamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: N-butyl-5-(3-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yloxy)-N-methylpentanamide
• 英文别名: N-butyl-5-[3-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-oxochromen-5-yl]oxy-N-methylpentanamide
• 化学式: C₂₈H₃₅NO₈
• 分子量: 513.588
• InChiKey: CGEATYDCBAWNBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4'-Hydroxywogonin 在 4-二甲氨基吡啶 、 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 N-butyl-5-(3-hydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yloxy)-N-methylpentanamide
  参考文献：
  名称：

  Synthesis of 3,5-dihydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)benzopyran-4-one derivatives as anticancer agents

  摘要：

  Different alkyl amide (15a-I) and alkyl amine (16a-e) derivatives of 7,8-dimethoxy-3-hydroxy-2-(4-methoxyphenyl)benzopyran-4-one were synthesized and evaluated for their anticancer activity against five different cancer cell lines using SRB assay. Compounds 15e, 15i, 15j and 16a-e showed significant anticancer activity within the range of IC50 2.58-34.86 mu M. The most promising molecule, 16c, was further analyzed for its effect on cell cycle and apoptosis of estrogen receptor positive cancer cells (MCF-7 cells) which showed that 16c triggered apoptosis in MCF-7 cells and arrested cells population at sub-G(0) (apoptotic) and G(2)M phase. In tubulin polymerization assay, 16c interfered with kinetics of tubulin polymerization. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.036

文献信息

• Synthesis of 3,5-dihydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)benzopyran-4-one derivatives as anticancer agents
  作者：Sarita Singh、Ateeque Ahmad、Dushyant Singh Raghuvanshi、Mohammad Hasanain、Karishma Agarwal、Vijaya Dubey、Kaniz Fatima、Sarfaraz Alam、Jayanta Sarkar、Suaib Luqman、Feroz Khan、Sudeep Tandon、Atul Gupta

  DOI：10.1016/j.bmcl.2016.09.036

  日期：2016.11

  Different alkyl amide (15a-I) and alkyl amine (16a-e) derivatives of 7,8-dimethoxy-3-hydroxy-2-(4-methoxyphenyl)benzopyran-4-one were synthesized and evaluated for their anticancer activity against five different cancer cell lines using SRB assay. Compounds 15e, 15i, 15j and 16a-e showed significant anticancer activity within the range of IC50 2.58-34.86 mu M. The most promising molecule, 16c, was further analyzed for its effect on cell cycle and apoptosis of estrogen receptor positive cancer cells (MCF-7 cells) which showed that 16c triggered apoptosis in MCF-7 cells and arrested cells population at sub-G(0) (apoptotic) and G(2)M phase. In tubulin polymerization assay, 16c interfered with kinetics of tubulin polymerization. (C) 2016 Elsevier Ltd. All rights reserved.