1-(2,4-dihydroxy-3-methyl-phenyl)-2-(3,4-dimethoxy-phenyl)ethanone | 116718-43-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(2,4-dihydroxy-3-methyl-phenyl)-2-(3,4-dimethoxy-phenyl)ethanone
• 英文别名: 2,4-dihydroxy-3-methylphenyl-3',4'-dimethoxybenzylketone；1-(2,4-dihydroxy-3-methylphenyl)-2-(3,4-dimethoxyphenyl)ethanone
• CAS: 116718-43-5
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: UAJDGLKDOYSVLE-UHFFFAOYSA-N

物化性质

• 沸点：
  500.5±40.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,4-dihydroxy-3-methyl-phenyl)-2-(3,4-dimethoxy-phenyl)ethanone 在 吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Synthesis, selective cytotoxicities and probable mechanism of action of 7-methoxy-3-arylflavone-8-acetic acids

  摘要：

  Thirteen new analogues of flavone-8-acetic acid, that is, compounds 10a-m bearing a methoxy group at the 7-position and diverse subsitiuents on the benzene ring at the 2- and 3-positions of flavone nucleus, were synthesized and evaluated for their direct antiproliferative effects on two human tumor cell lines and for their indirect antiproliferative activities in the transwell co-culture system. The results indicated that most of compounds 10a-m showed moderate direct cytotoxicities. Among them, compound 10i exhibited higher direct cytotoxicity and selectivity for both cell lines over BJ human foreskin fibroblast cells than 5,6-dimethylxanthenone-4-acetic acid (DMXAA). Interestingly, compared with DMXAA, compound 10e showed comparable indirect cytotoxicity and higher selectivity. In addition, compound 10e was found to be able to induce tumor necrosis factor alpha (TNF-alpha) production in human peripheral blood mononuclear cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.042
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酸 、 2,6-二羟基甲苯 在 三氟化硼乙醚 作用下， 生成 1-(2,4-dihydroxy-3-methyl-phenyl)-2-(3,4-dimethoxy-phenyl)ethanone
  参考文献：
  名称：

  异黄酮的氧化二聚：葛根黄酮A及其相关化合物的合成*

  摘要：

  Kudzuisoflavone-A是在氯化亚铜存在下通过大豆苷元的氧化二聚作用成功合成的。当用三氟乙酸th处理时，适当取代的异黄酮也进行区域选择性氧化二聚，从而以高收率得到新的6'，6'''-二异黄酮。提出了区域选择性的基本原理。

  DOI：

  10.1071/ch12108

文献信息

• Oxidative Dimerisation of Isoflavones: Synthesis of Kudzuisoflavone A and Related Compounds
  作者：Mandar Deodhar、Kasey Wood、David StClair Black、Naresh Kumar

  DOI：10.1071/ch12108

  日期：——

  Kudzuisoflavone-A was successfully synthesised via oxidative dimerisation of daidzein in the presence of cuprous chloride. Appropriately substituted isoflavones also undergo regioselective oxidative dimerisation when treated with thallium trifluoroacetate to give novel 6′,6′″-biisoflavones in good yield. A rationale for the regioselectivity is proposed.

  Kudzuisoflavone-A是在氯化亚铜存在下通过大豆苷元的氧化二聚作用成功合成的。当用三氟乙酸th处理时，适当取代的异黄酮也进行区域选择性氧化二聚，从而以高收率得到新的6'，6'''-二异黄酮。提出了区域选择性的基本原理。
• [EN] SUBSTITUTED CHROMAN DERIVATIVES, MEDICAMENTS AND USE IN THERAPY<br/>[FR] DÉRIVÉS DE CHROMANE SUBSTITUÉS, MÉDICAMENTS ET UTILISATION À DES FINS THÉRAPEUTIQUES
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2006032085A1

  公开（公告）日：2006-03-30

  Novel substituted chroman derivatives and intermediate compounds, compositions containing same, methods for their preparation and uses thereof as therapeutic agents particularly as anti-cancer and chemotherapeutic selective agents are described.

  描述了新型替代色呐衍生物和中间化合物、含有这些化合物的组合物、其制备方法以及作为治疗剂的用途，特别是作为抗癌和化疗选择性剂。
• Benzopyrans and use thereof in treating vascular diseases
  申请人：Zyma SA

  公开号：US04814346A1

  公开（公告）日：1989-03-21

  Isoflavans of the formula I ##STR1## wherein the groups OR, R', R" and ring B are as defined in the specification, exhibit valuable pharmacological properties, especially for the treatment of vascular diseases. They are prepared by methods known per se.

  公式为I ##STR1## 中的异黄酮，其中基团OR、R'、R"和环B的定义如规范中所述，具有有价值的药理特性，特别适用于治疗血管疾病。它们可通过已知的方法制备。
• SUBSTITUTED CHROMAN DERIVATIVES, MEDICAMENTS AND USE IN THERAPY
  申请人：HEATON Andrew

  公开号：US20090317490A1

  公开（公告）日：2009-12-24

  Novel substituted chroman derivatives and intermediate compounds, compositions containing same, methods for their preparation and uses thereof as therapeutic agents particularly as anti-cancer and chemotherapeutic selective agents are described.

  本发明描述了代替的色甘醇衍生物和中间化合物，包含它们的组合物，制备它们的方法以及它们作为治疗剂的用途，特别是作为抗癌和化学治疗选择性剂。
• Isoflavonoid Dimers
  申请人：Heaton Andrew

  公开号：US20080306140A1

  公开（公告）日：2008-12-11

  Novel compounds based on phenyl-substituted naphtho[1,2-g]chrysene compounds (A) are described. The compounds are obtainable by dimerisation of 3-phenylchroman (isoflavonoid) ring systems (B). Methods of synthesis of the novel dimeric compounds, compositions containing same and use of the dimers as therapeutic agents are also described.

  本发明描述了基于苯基取代的萘并[1,2-g]花菁化合物(A)的新化合物。这些化合物可通过3-苯基异黄酮(B)环系统的二聚化获得。本发明还描述了新二聚化合物的合成方法、含有同样化合物的组合物以及将这些二聚体用作治疗剂的用途。