7,4'-dimethyl-6-iodoapigenin | 50848-66-3

• 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: 7,4'-dimethyl-6-iodoapigenin
• 英文别名: 7,4'-Dimethoxy-5-hydroxy-6-iodoflavone；5-hydroxy-6-iodo-7-methoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 50848-66-3
• 化学式: C₁₇H₁₃IO₅
• 分子量: 424.192
• InChiKey: LYXXSEPXNUAEHX-UHFFFAOYSA-N

物化性质

• 熔点：
  227-228 °C
• 沸点：
  522.4±50.0 °C(Predicted)
• 密度：
  1.711±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7,4'-dimethyl-6-iodoapigenin 在 sodium hydroxide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 robustaflavone hexamethyl ether
  参考文献：
  名称：

  Total Synthesis of Robustaflavone, a Potential Anti-Hepatitis B Agent

  摘要：

  Robustaflavone, a naturally occurring compound, is an inhibitor of hepatitis B virus replication in vitro. Robustaflavone is a biflavanoid composed of two units of apigenin (5,7,4'-trihydroxyflavone) joined via a biaryl linkage between the g-position of one unit and the 3'-position of the other (I6,II3'-biapigenin). The natural material was isolated from the seed-kernels of Rhus succedanea. To provide ready access to sufficient quantities of material for continued biological studies, as well as to provide a general route for the preparation of structural analogues, a total synthesis of robustaflavone was pursued. The total synthesis was approached by constructing apigenin ethers containing functionalities at the 6- and 3'-positions which could be cross-coupled using transition metal catalysis. Key steps of the synthesis included development of a regioselective iodination of an apigenin derivative at the 6-position. Also key was the formation of an apigenin 3'-boronate using a palladium-catalyzed exchange of the corresponding 3'-iodide with a diboron reagent. Finally, identification of appropriate reaction conditions for Suzuki coupling to form the sterically congested 6-3''' biaryl bond of robustaflavone provided access to the desired biflavanoid system. This work represents the first total synthesis of robustaflavone.

  DOI：

  10.1021/jo981186b
• 作为产物：
  描述：

  地奥司明 在 palladium on activated charcoal 盐酸 、 甲酸铵 、 potassium carbonate 、 potassium hydrogencarbonate 、 N,N,N-trimethylbenzenemethanaminium dichloroiodate 、 calcium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 7,4'-dimethyl-6-iodoapigenin
  参考文献：
  名称：

  Semisynthesis of Linarin, Acacetin, and 6-Iodoapigenin Derivatives from Diosmin

  摘要：

  Semisynthesis of linarin and acacetin from the Citrus flavonoid diosmin was performed via, as first intermediate, the 3'-O-phenyltetrazolyl ether of diosmin. This paper relates also a semisynthetic access to 6-iodoapigenin derivatives, which are key compounds in the synthesis of some biflavonoids such as robustaflavone.

  DOI：

  10.1021/np040079b

文献信息

• Chromenone derivatives useful for the treatment of neurodegenerative diseases
  申请人：AxoGlia Therapeutics S.A.

  公开号：EP2112145A1

  公开（公告）日：2009-10-28

  Compounds of general formula (I) and (II) in which R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14 and R15 have the meanings given in the specification, are useful in the treatment of neurodegenerative disease.

  通式（I）和（II）的化合物 其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14和R15具有规范中给定的含义，在神经退行性疾病的治疗中是有用的。
• Regioselective 6-iodination of 5,7-dioxygenated flavones by benzyltrimethylammonium dichloroiodate
  作者：Jérôme Quintin、Guy Lewin

  DOI：10.1016/j.tetlet.2004.03.038

  日期：2004.4

  The iodination of 5,7-dioxygenated flavones with 1 equiv of benzyltrimethylammonium dichloroiodate (BTMA·ICl2) in the system CH2Cl2–MeOH–CaCO3 at room temperature is presented in this note. Flavones with a free phenol group at C5 and an alkoxy or a peracylglycosyloxy at C7 lead to the 6-iodoflavones with a good regioselectivity (ratio 6-iodination/8-iodination about 9).

  本说明介绍了在室温下，在系统CH 2 Cl 2 -MeOH-CaCO 3中用1当量的苄基三甲基二氯碘酸铵（BTMA·ICl 2）对5,7-双加氧黄酮进行碘化。在C5处具有游离酚基的黄酮和在C7处具有烷氧基或过酰基糖基糖氧基的黄酮导致具有良好区域选择性的6-碘黄酮（6-碘化/ 8-碘化比约为9）。
• Robustaflavone, intermediates and analogues and method for preparation thereof
  申请人：Advanced Life Sciences, Inc.

  公开号：US06225481B1

  公开（公告）日：2001-05-01

  Robustaflavone, intermediates and analogues thereof and a method for synthesizing the same are provided. The method involves constructing apigenin ethers containing functionalities at the 6- and 3′-positions which could be cross-coupled using transition metal catalysis. The method also involves development of a regioselective iodination of an apigenin derivative at the 6-position, formation of an apigenin 3′-boronate using a palladium-catalyzed exchange of the corresponding 3′-iodide with a diboron reagent. Finally, Suzuki coupling to form the sterically congested 6-3′″ biaryl bond of robustaflavone provides access to the desired biflavanoid system. Robustaflavone intermediates and analogues may be used to prepare analogues of other biflavanoids such as hinokifavone, rhusflavone and succedaneaflavone.

  本文提供了Robustaflavone、其中间体和类似物的合成方法。该方法涉及构建含有6位和3'位官能团的黄烷酮醚，可以使用过渡金属催化交叉偶联。该方法还涉及开发一种在6位上碘化黄烷酮衍生物的区域选择性碘化方法，使用钯催化将相应的3'位碘化物与二硼试剂交换形成黄烷酮3'硼酸酯。最后，使用Suzuki偶联反应形成Robustaflavone的立体阻碍的6-3'双芳基键，从而获得所需的双黄烷类系统。Robustaflavone中间体和类似物可用于制备其他双黄烷类化合物的类似物，如hinokifavone、rhusflavone和succedaneaflavone。
• CHROMENONE DERIVATIVES USEFUL FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：Coowar Djalil

  公开号：US20110144194A1

  公开（公告）日：2011-06-16

  Compounds of general formula (I) and (II) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 have the meanings given in the specification, are useful in the treatment of neurodegenerative disease.

  通式（I）和（II）的化合物，其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14和R15的含义如规范中所述，对于治疗神经退行性疾病是有用的。
• Synthesis and cytotoxic activities of 8- and 6-demethyleucalyptins
  作者：Ryuki Asakawa、Kanta Fuchiyama、Yunosuke Ishii、Keisuke Hosaka、Atsushi Kobayashi、Kei Shimazaki、Junki Nagasawa、Sayaka Tsuchida、Kazunari Ushida、Makoto Matsubayashi、Yuuki Furuyama、Kenji Ohgane、Kouji Kuramochi

  DOI：10.1093/bbb/zbac105

  日期：2022.8.24

  synthesized. The isolated compound was unambiguously determined to be 8-demethyleucalyptin by comparing its NMR data with those of the synthetic ones. Cytotoxic evaluation of 8- and 6-demethyleucalyptins revealed that only the former showed cytotoxicity against HCT116 and MRC-5 cells. The present study provides not only easy access to 8- and 6-demethyleucalyptins, but also their biological information

  植物中的次生代谢物会影响食草动物的健康，例如以高山植物的叶子和果实为食的日本岩雷鸟。因此，了解高山植物的次生代谢物及其生物活性对于保护日本岩雷鸟非常重要。我们从日本岩雷鸟赖以生存的 Kalmia procumbens 的叶子中分离出 C-甲基黄酮。虽然通过将其核磁共振（NMR）数据与报道的数据进行比较，推断其结构为8-去甲基桉树碱，但不能排除分离的化合物是6-去甲基桉树碱的可能性。因此，合成了两种异构体。通过将其核磁共振数据与合成的核磁共振数据进行比较，可以明确确定分离的化合物是 8-去甲基桉树碱。8-和 6-去甲基桉树素的细胞毒性评估表明，只有前者对 HCT116 和 MRC-5 细胞具有细胞毒性。本研究不仅提供了轻松获取 8-和 6-去甲基桉树素的途径，还提供了它们的生物学信息。