5,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2H-1-benzopyran-2-one | 88126-50-5

• 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: 5,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2H-1-benzopyran-2-one
• 英文别名: 5,7,3',4'-Tetramethoxy-4-phenyl-2H-1-benzopyran-2-one；5,7,3',4'-tetramethoxy-4'-phenylcoumarin；5,7,3',4'-tetramethoxy-4-phenylcoumarin；4-(3,4-Dimethoxyphenyl)-5,7-dimethoxy-2H-1-benzopyran-2-one；4-(3,4-dimethoxyphenyl)-5,7-dimethoxychromen-2-one
• CAS: 88126-50-5
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: ISGCRTXQJLZTNL-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：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-hydroxy-5,7-dimethoxycoumarin 在 copper(l) iodide 、 四(三苯基膦)钯 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 5,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of neoflavones by Suzuki arylation of 4-substituted coumarins

  摘要：

  在铃木反应条件下，钯催化 4-氯或 4-溴香豆素 1-4 与芳基硼酸 5-13 的偶联反应是获得 4-芳基香豆素的有效途径。在改良的铃木反应条件下，使用碘化铜（I）作为辅助催化剂，将 4-三氟甲基-磺酰氧基香豆素 35-38 与芳基硼酸进行处理，也能以良好的收率（70-97%）获得这些 4-芳基香豆素。

  DOI：

  10.1039/p19960002591

文献信息

• Synthesis of 4-arylcoumarins from Coutarea hexandra
  作者：G Monache

  DOI：10.1016/s0031-9422(00)81132-2

  日期：——

  Abstract The structures assigned to the 5,7-dimethoxy-4-arylcoumarins isolated from Coutarea hexandra have been confirmed by synthesis, via Pechmann condensation of phloroglucinol and an ethyl benzoylacetate derivative, the hydroxy groups of which were protected either by benzylation or by methylenedioxy group formation.

  摘要 从 Coutarea hexandra 中分离出的 5,7-二甲氧基-4-芳基香豆素的结构已通过间苯三酚和苯甲酰乙酸乙酯衍生物的 Pechmann 缩合合成得到证实，其羟基被苄基化或亚甲二氧基保护。形成。
• Synthesis and antiprotozoal activity of 4-arylcoumarins
  作者：Jean-Thomas Pierson、Aurélien Dumètre、Sébastien Hutter、Florence Delmas、Michèle Laget、Jean-Pierre Finet、Nadine Azas、Sébastien Combes

  DOI：10.1016/j.ejmech.2009.10.022

  日期：2010.3

  synthesized by Suzuki-Miyaura cross-coupling reaction and evaluated for antiprotozoal activity against Plasmodium falciparum and Leishmania donovani. Several compounds were found to strongly inhibit the proliferation of human cell line and/or parasites. The 4-(3,4-dimethoxyphenyl)-6,7-dimethoxycoumarin exhibit a potent activity on L. donovani amastigotes with a selectivity index (SI = 265) twice than

  Suzuki-Miyaura交叉偶联反应合成了大量的4-芳基香豆素，并评估了其对恶性疟原虫和多形利什曼原虫的抗原生动物活性。发现几种化合物强烈抑制人细胞系和/或寄生虫的增殖。4-（3,4-二甲氧基苯基）-6,7-二甲氧基展览上的有效活性杜氏利什曼原虫的选择性指数（SI = 265）比两性霉素B（SI = 140）两次无鞭毛体。
• A facile synthesis of 4-aryl-2H-1-benzopyran-2-ones
  作者：Vinod K. Ahluwalia、Daljeet Singh、Rishi P. Singh

  DOI：10.1007/bf00809163

  日期：——
• 4-Arylcoumarins from Coutarea hexandra
  作者：Giuliano Delle Monache、Bruno Botta、Amaro Serafim Neto、Roberto Alves De Lima

  DOI：10.1016/0031-9422(83)80104-6

  日期：1983.1
• Cytotoxic Constituents of the Roots of Exostema acuminatum
  作者：Aiko Ito、Hee-Byung Chai、Young Geun Shin、Ricardo Garcı́a、Miliciades Mejı́a、Qi Gao、Craig R Fairchild、Kate E Lane、Ana T Menendez、Norman R Farnsworth、Geoffrey A Cordell、John M Pezzuto、A Douglas Kinghorn

  DOI：10.1016/s0040-4020(00)00584-6

  日期：2000.8

  Bioassay-guided phytochemical investigation of the roots of Exostema acuminatum (Rubiaceae) using human oral epidermoid carcinoma (KB) cells as a monitor, led to the isolation of two norditerpenoids, namely, (16R)-ent-16,17-dihydroxy-19-nor-kaur-4-en-3-one (1) and (16S)-ent-16,17-dihydroxy-19-nor-kaur-4-en-3-one (2), and six previously known 4-phenylcoumarins (3-8). The structure and relative stereochemistry of the novel compound 1 were determined by X-ray crystallography. All isolates were tested against a panel of human tumor cell lines, and the 4-phenylcoumarins showed significant cytotoxicity, with 3'-hydroxy-5,7,4'-trimethoxy-4-phenylcoumarin (5) and 8-hydroxy-5,7,4'-trimethoxy-4-phenylcoumarin (6) exhibiting the most potent activity. Two of the 4-phenylcoumarins, 5,7,4'-trimethoxy-4-phenylcoumarin (3) and 6, were evaluated in an in vivo P388 murine leukemia model. (C) 2000 Elsevier Science Ltd. All rights reserved.