3',4',6,7-tetramethoxy-isoflavone | 24126-93-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3',4',6,7-tetramethoxy-isoflavone
• 英文别名: 6,7,3',4'-tetramethoxyisoflavone；3',4',6,7-Tetramethoxy-isoflavon；3-(3,4-dimethoxyphenyl)-6,7-dimethoxychromen-4-one
• CAS: 24126-93-0
• 化学式: C₁₉H₁₈O₆
• mdl: MFCD05861580
• 分子量: 342.348
• InChiKey: OYSKBZHHLYECLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  3',4',6,7-tetramethoxy-isoflavone 在 sodium hydrogen telluride 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以70.7%的产率得到6,7,3',4'-tetramethoxyisoflavanone
  参考文献：
  名称：

  Jain; Kumar; Sharma, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 2, p. 290 - 291

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3-三甲氧基苯 在 三氯化铝 、 formamide 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3',4',6,7-tetramethoxy-isoflavone
  参考文献：
  名称：

  Villa, Maria Jesus; Dominguez, Esther; Lete, Esther, Heterocycles, 1986, vol. 24, # 7, p. 1943 - 1954

  摘要：

  DOI：

文献信息

• Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities
  作者：Hideyuki Goto、Yoshiyasu Terao、Shuji Akai

  DOI：10.1248/cpb.57.346

  日期：——

  Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10′) were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12—54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E—I) and their biphenyl-ketone derivatives (10E—H) also showed a high activity (ED50=<50 μM), while all of their corresponding isoflavones (8E—I) were not active at all. The 7-hydroxyisoflavanes having either an additional hydroxyl group at the C5-position (9D) or a methoxy group at the C6-position (9J) presented a high activity (ED50=26—32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3′-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10′) by metabolism or biotransformation.

  合成了四十八种异黄酮（8）、三十一种异黄烷（9）以及四十七种联苯酮（10, 10′），这些化合物是由十一种取代酚（11）和六种苯乙酸（12）合成的。其中，有七十五种化合物是新发现的。这些化合物的自由基清除活性在pH 6.0下使用1,1-二苯基-2-吡唑啉酮（DPPH）进行了评估。我们发现，在四十三种含有儿茶酚基的化合物中，三十九种在A环或B环上表现出与儿茶素相似的高活性（ED50=12—54 μM）。在这些情况下，它们结构的其他部分似乎对活性影响不大。许多6-或8-羟基异黄烷（9E—I）及其联苯酮衍生物（10E—H）也显示出高活性（ED50=<50 μM），而它们对应的异黄酮（8E—I）则完全没有活性。具有在C5位增加羟基（9D）或在C6位增加甲氧基（9J）的7-羟基异黄烷则展现出高活性（ED50=26—32 μM）。本研究表明，天然异黄酮通过在C6、C8或C3′位置的羟基化，或通过代谢或生物转化形成异黄烷（9）和/或联苯酮衍生物（10′），具有表现抗氧化活性的可能性。
• Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity
  作者：Victor V. Semenov、Dmitry V. Tsyganov、Marina N. Semenova、Roman N. Chuprov-Netochin、Mikhail M. Raihstat、Leonid D. Konyushkin、Polina B. Volynchuk、Elena I. Marusich、Vera V. Nazarenko、Sergey V. Leonov、Alex S. Kiselyov

  DOI：10.1021/acs.jnatprod.6b00173

  日期：2016.5.27

  8 followed by their Cu(I)-mediated cyclization into the target series 9. The biological activity of GVA and its derivatives was evaluated using a panel of seven human cancer cell lines and an in vivo sea urchin embryo assay. Both screening platforms confirmed the antimitotic effect of the parent GVA (9cg) and its alkoxy derivatives. Structure–activity relationship studies suggested that compounds 9cd

  开发了一种简明的六步方案，从莳萝和香菜种子中容易获得的植物代谢物开始合成异黄酮glaziovianin A（GVA）及其烷氧基苯基衍生物9。反应顺序包括将关键的中间环氧化物7有效转化为相应的β-酮醛8，然后将它们的Cu（I）介导的环化反应转化为目标序列9。使用一组七种人类癌细胞系和体内海胆胚胎测定法评估了GVA及其衍生物的生物活性。两个筛选平台均证实了亲本GVA（9cg）及其烷氧基衍生物。结构与活性之间的关系研究表明，分别被三甲氧基和莳萝酚衍生的B环取代的化合物9cd和9cf的活性低于母体9cg。在评估的人类癌细胞系中，A375黑色素瘤细胞系对被测分子最敏感。值得注意的是，目标化合物对浓度高达10μM的人外周血单核细胞没有细胞毒性。海胆测定的表型读数明确表明异黄酮9cg，9cd和9cf具有直接的微管破坏作用。
• Isocladrastin and kashmigenin—two isoflavones from Iris kashmiriana
  作者：T.K. Razdan、P.K. Kachroo、B. Qadri、A.K. Kalla、S.C. Taneja、S.K. Koul、K.L. Dhar

  DOI：10.1016/0031-9422(95)00575-7

  日期：1996.2

  Abstract From the rhizomes of the Iris kashmiriana , two new isoflavones, isocladrastin and kashmigenin, were characterized as 3′-hydroxy-6,7-4′-trimethoxy-isoflavone and 4′-hydroxy-3′,5′-dimethoxy-6,7-methylenedioxy-isoflavone, respectively. Also, junipegenin-B has been found present in this plant species.

  摘要 从克什米尔鸢尾的根茎中，鉴定出两种新的异黄酮，isocladrastin 和 kashmigenin，分别为 3'-羟基-6,7-4'-三甲氧基-异黄酮和 4'-羟基-3',5'-二甲氧基-6 ,7-亚甲二氧基异黄酮，分别。此外，还发现杜松素 B 存在于该植物物种中。
• Method of decreasing liquiritigenin-derived isoflavones relative to total isoflavones in plants and plants producing reduced ratio of liquiritigenin-derived isoflavones relative to total isoflavones
  申请人：——

  公开号：US20040128714A1

  公开（公告）日：2004-07-01

  This invention pertains to methods for decreasing the ratio of liquiritigenin-derived isoflavones relative to total isoflavone levels in isoflavonoid-producing plants and plant parts by transforming plants with a recombinant DNA construct comprising a nucleic acid sequence of at least 200 nucleotides and having at least 75% sequence identity to a polynucleotide encoding a chalcone reductase. More preferably, this invention pertains to methods for decreasing the ratios of daidzein and glycitein and their conjugates relative to total isoflavone levels in soybean plants and soybean plant parts by transforming plants with a recombinant DNA construct comprising a nucleic acid sequence of at least 200 nucleotides and having at least 75% sequence identity to a polynucleotide encoding a chalcone reductase.

  本发明涉及通过用重组 DNA 构建体转化植物来降低产生异黄酮的植物和植物部位中来源于利吉霉素的异黄酮相对于总异黄酮水平的比率的方法，该 DNA 构建体包含至少 200 个核苷酸的核酸序列，并且与编码查耳酮还原酶的多核苷酸具有至少 75% 的序列同一性。更优选地，本发明涉及通过用重组 DNA 构建体转化植物来降低大豆植物和大豆植物部位中的大豆异黄酮和甘草甜素及其共轭物相对于总异黄酮水平的比率的方法，该 DNA 构建体包含至少 200 个核苷酸的核酸序列，且与编码查尔酮还原酶的多核苷酸具有至少 75% 的序列同一性。
• One-step conversion of flavanones into isoflavones: a new facile biomimetic synthesis of isoflavones
  作者：Takeshi Kinoshita、Koji Ichinose、Ushio Sankawa

  DOI：10.1016/s0040-4039(00)88565-2

  日期：1990.1