3,4-dihydro-5,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)coumarin | 1013933-93-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3,4-dihydro-5,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)coumarin
• 英文别名: Neoflavonoid, 11；5,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrochromen-2-one
• CAS: 1013933-93-1
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: QXGJGLQOJFSBPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  吡咯 、 3,4-dihydro-5,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)coumarin 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以48%的产率得到3-(2-hydroxy-4,6-dimethoxyphenyl)-1-(1H-pyrrol-1-yl)-3-(3,4,5-trimethoxyphenyl)propan-1-one
  参考文献：
  名称：

  Reduction of Pyrrolyl- and Indolylamides with BH₃·THF: Cyclodeoxygenation versus Deoxygenation

  摘要：

  Herein we report that borane reductions of acylpyrroles and acylindoles that contain a pendant phenol take two different paths. Acylpyrroles undergo a reductive cyclization to make unusual chromanyl pyrroles. Treatment of related acylindoles under identical conditions results in deoxygenation without cyclization. The results are interpreted in terms of relative rates of cyclization and reduction of intermediate carbenium ions, where cyclization of the indole-stablized carbenium ion is slower.

  DOI：

  10.1021/jo801627z
• 作为产物：
  描述：

  3,5-二甲氧基苯酚 、 methyl 3,4,5-trimethoxycinnamate 在 三氟乙酸 作用下， 反应 75.0h， 以29%的产率得到3,4-dihydro-5,7-dimethoxy-4-(3,4,5-trimethoxyphenyl)coumarin
  参考文献：
  名称：

  Design and Synthesis of C-Ring Lactone- and Lactam-Based Podophyllotoxin Analogues as Anticancer Agents

  摘要：

  合成了一系列新的蒽醌类（PDT）类似物，其中内酯部分被移至C环。一些衍生物的A环也进行了改造。类似物23和25在体外对结肠癌（CaCO2）细胞系表现出强的细胞毒性。去甲基化的E环类似物的效力优于相应的甲基化类似物。这些类似物对人红细胞的毒性与PDT相当，尽管浓度要高得多（100 μg/ml），才显示出其细胞毒性值。

  DOI：

  10.1248/cpb.58.242

文献信息

• Design and Synthesis of C-Ring Lactone- and Lactam-Based Podophyllotoxin Analogues as Anticancer Agents
  作者：Pragya Singh、Uzma Faridi、Suchita Srivastava、Jonnala Kotesh Kumar、Mahender Pandurang Darokar、Suaib Luqman、Karuna Shanker、Chandan Singh Chanotiya、Atul Gupta、Madan Mohan Gupta、Arvind Singh Negi

  DOI：10.1248/cpb.58.242

  日期：——

  A series of novel podophyllotoxin (PDT) analogues was synthesized in which the lactone moiety was shifted to C ring. Some of the derivatives were also synthesized with modified A ring. Analogues 23 and 25 exhibited potent in vitro cytotoxicity against colon cancer (CaCO2) cell line. p-Demethylated E-ring analogues exhibited better potency than the corresponding methylated analogues. These analogues showed toxicity comparable to PDT against human erythrocytes albeit at much higher concentrations (100 μg/ml) than their cytotoxicity values.

  合成了一系列新的蒽醌类（PDT）类似物，其中内酯部分被移至C环。一些衍生物的A环也进行了改造。类似物23和25在体外对结肠癌（CaCO2）细胞系表现出强的细胞毒性。去甲基化的E环类似物的效力优于相应的甲基化类似物。这些类似物对人红细胞的毒性与PDT相当，尽管浓度要高得多（100 μg/ml），才显示出其细胞毒性值。
• Reduction of Pyrrolyl- and Indolylamides with BH₃·THF: Cyclodeoxygenation versus Deoxygenation
  作者：Kelin Li、Jon A. Tunge

  DOI：10.1021/jo801627z

  日期：2008.11.7

  Herein we report that borane reductions of acylpyrroles and acylindoles that contain a pendant phenol take two different paths. Acylpyrroles undergo a reductive cyclization to make unusual chromanyl pyrroles. Treatment of related acylindoles under identical conditions results in deoxygenation without cyclization. The results are interpreted in terms of relative rates of cyclization and reduction of intermediate carbenium ions, where cyclization of the indole-stablized carbenium ion is slower.