(±)-7-methoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrocoumarin | 243666-37-7

• 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: (±)-7-methoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrocoumarin
• 英文别名: (+/-)-7-methoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrocoumarin；3,4-dihydro-7-methoxy-4-(3,4,5-trimethoxyphenyl)coumarin；Neoflavonoid, 10；7-methoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrochromen-2-one
• CAS: 243666-37-7
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: PRCIEPQIRAKFCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (±)-7-methoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrocoumarin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以67%的产率得到7-methoxy-4-(3,4,5-trimethoxyphenyl)chromen-2-one
  参考文献：
  名称：

  细胞毒性 4-芳基香豆素的短合成

  摘要：

  摘要描述了在 CF3COOH 存在下，通过酚类与肉桂酸缩合，然后用 DDQ 脱氢，快速合成细胞毒性 4-芳基香豆素。

  DOI：

  10.1080/00397910500501235
• 作为产物：
  描述：

  3-甲氧基苯酚 、 3,4,5-三甲氧基肉桂酸 在 三氟化硼乙醚 、 三氯氧磷 作用下， 反应 0.25h， 以57.2%的产率得到(±)-7-methoxy-4-(3,4,5-trimethoxyphenyl)-3,4-dihydrocoumarin
  参考文献：
  名称：

  Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins

  摘要：

  通过取代肉桂酸和3-芳基炔酸与相应的酚反应，合成了一系列4-芳基-3,4-二氢香豆素和4-芳基香豆素。这些化合物在体外评估了抗菌活性。合成的化合物对金黄色葡萄球菌、大肠杆菌、痢疾杆菌和白色念珠菌（真菌）表现出不同程度的抗微生物活性。具有羟基苯环和7,8-取代二羟基的A环化合物是最活跃的抗微生物剂。

  DOI：

  10.1007/s10600-012-0149-9

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。
• Synthesis and antimicrobial activities of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins
  作者：Jie Sun、Wei-Xian Ding、Xiao-Ping Hong、Ke-Yun Zhang、Yong Zou

  DOI：10.1007/s10600-012-0149-9

  日期：2012.3

  A new series of 4-aryl-3,4-dihydrocoumarins and 4-arylcoumarins were synthesized by the reaction of substituted cinnamic acids and 3-arylpropiolic acid with the corresponding phenols. These compounds were evaluated for antibacterial activity in vitro. The synthesized compounds displayed different degrees of antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Bacillus dysenteriae, and Candida albicans (a fungus). Compounds with catechol moieties and 7,8-substituted dihydroxyls in the A ring were the most active antimicrobial agents.

  通过取代肉桂酸和3-芳基炔酸与相应的酚反应，合成了一系列4-芳基-3,4-二氢香豆素和4-芳基香豆素。这些化合物在体外评估了抗菌活性。合成的化合物对金黄色葡萄球菌、大肠杆菌、痢疾杆菌和白色念珠菌（真菌）表现出不同程度的抗微生物活性。具有羟基苯环和7,8-取代二羟基的A环化合物是最活跃的抗微生物剂。
• Substituted 4h-chromens, 2h-chromenes, chromans and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20050176750A1

  公开（公告）日：2005-08-11

  The present invention is directed to substituted 4H-chromenes, 2H-chromenes, chromans and analogs thereof, represented by the general Formula (I) wherein R 5 , A, B, X, Y, Z and dotted lines are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被代替的4H-色烯、2H-色烯、色烷及其类似物，由通式（I）所表示，其中R5、A、B、X、Y、Z和虚线在此定义。本发明还涉及发现具有通式（I）的化合物是caspase的激活剂和凋亡的诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床情况下出现的异常细胞的无控制生长和扩散的细胞死亡。
• Synthesis of Substituted (±)-3,4-Dihydrocoumarins Using H-Y Zeolite
  作者：Manojkumar R. Shukla、Prashant N. Patil、Prakash P. Wadgaonkar、Prafulla N. Josh、Manikrao M. Salunkhe

  DOI：10.1080/00397910008087290

  日期：2000.1

  Synthesis of substituted (+/-)-3,4 Dihydrocoumarins were prepared with the reaction between substituted cinnamic acid and phenol catalysed by eco-friendly solid-acid catalyst H-Y zeolite involving esterification followed by ring closure.
• Shukla; Padiya; Patil, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 3, p. 372 - 375
  作者：Shukla、Padiya、Patil、Salunkhe

  DOI：——

  日期：——