(6-Chloro-2-oxo-2H-1-benzopyran-4-yl)methyl 3-methyl-2-butenoate | 484000-53-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (6-Chloro-2-oxo-2H-1-benzopyran-4-yl)methyl 3-methyl-2-butenoate
• 英文别名: (6-chloro-2-oxochromen-4-yl)methyl 3-methylbut-2-enoate
• CAS: 484000-53-5
• 化学式: C₁₅H₁₃ClO₄
• 分子量: 292.719
• InChiKey: FYFQYIOWJAGYRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 在 硫酸 、 双氧水 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 50.5h， 生成 (6-Chloro-2-oxo-2H-1-benzopyran-4-yl)methyl 3-methyl-2-butenoate
  参考文献：
  名称：

  Preliminary Structure–Antiangiogenic Activity Relationships of 4-Senecioyloxymethyl-6,7-dimethoxycoumarin

  摘要：

  Through a systematic modification of the novel angiogenesis inhibitor 4-senecioyloxymethyl-6,7-dimethoxycoumarin (1) we found that a 6,7-dimethoxy moiety is important for bioactivity of 1. Replacement of the lactone functionality in coumarin 1 by an amide decreased its activity. By substitution of the senecioyl chain with various cinnamoyl groups we discovered 6d, bearing a 4-methoxycinnamoyl instead of senecioyl side chain, with inhibitory activity in HUVEC tube formation assay enhanced by one order of magnitude compared to 1. We have also synthesized compound 12, an analogue of 6d, with equipotency and improved water solubility. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00392-x

文献信息

• Preliminary Structure–Antiangiogenic Activity Relationships of 4-Senecioyloxymethyl-6,7-dimethoxycoumarin
  作者：Nguyen-Hai Nam、Yong Kim、Young-Jae You、Dong-Ho Hong、Hwan-Mook Kim、Byung-Zun Ahn

  DOI：10.1016/s0960-894x(02)00392-x

  日期：2002.9

  Through a systematic modification of the novel angiogenesis inhibitor 4-senecioyloxymethyl-6,7-dimethoxycoumarin (1) we found that a 6,7-dimethoxy moiety is important for bioactivity of 1. Replacement of the lactone functionality in coumarin 1 by an amide decreased its activity. By substitution of the senecioyl chain with various cinnamoyl groups we discovered 6d, bearing a 4-methoxycinnamoyl instead of senecioyl side chain, with inhibitory activity in HUVEC tube formation assay enhanced by one order of magnitude compared to 1. We have also synthesized compound 12, an analogue of 6d, with equipotency and improved water solubility. (C) 2002 Elsevier Science Ltd. All rights reserved.