6-乙酰氨基-6-去氧-亚麻子精 | 75199-40-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 6-乙酰氨基-6-去氧-亚麻子精
• 英文名称: 6,7-dimethoxy-4'-hydroxy-isoflavone
• 英文别名: 3-(4-Hydroxyphenyl)-6,7-dimethoxychromen-4-one
• CAS: 75199-40-5
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: PWSUUSZLVOWNGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 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：

  6-乙酰氨基-6-去氧-亚麻子精 在 aluminum (III) chloride 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以92%的产率得到4’,6,7-三羟异黄酮
  参考文献：
  名称：

  Facile Method for the Large-Scale Synthesis of 6,7,4′-Trihydroxyisoflavanone

  摘要：

  6,7,4 '-Trihydroxyisoflavanone, the main source of which is extracted from soybeans, has been found to have diverse significant bioactivities. A large-scale, cost-effective, and facile chemical synthesis of 6,7,4 '-trihydroxyisoflavanone is presented herein. Its synthesis is characterized by three steps with an overall yield of 71% and a purity or more than 99.0%. This reaction can be scaled up to multikilogram quantities, providing a solid basis for its further bioactivity studies and drug development. With this same method, 6,7,3 ',4 '-tetrahydroxyisoflavanone, an analog of 6,7,4 '-trihydroxyisoflavanone, also can be largely prepared, indicating this modified synthetic method is potentially available for large-scale synthesis of a broad range of multihydroxyl isoflavanones.

  DOI：

  10.1080/00397911.2014.886331
• 作为产物：
  描述：

  对羟基苯乙腈 在 盐酸 、 三氟化硼乙醚 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 6-乙酰氨基-6-去氧-亚麻子精
  参考文献：
  名称：

  Facile Method for the Large-Scale Synthesis of 6,7,4′-Trihydroxyisoflavanone

  摘要：

  6,7,4 '-Trihydroxyisoflavanone, the main source of which is extracted from soybeans, has been found to have diverse significant bioactivities. A large-scale, cost-effective, and facile chemical synthesis of 6,7,4 '-trihydroxyisoflavanone is presented herein. Its synthesis is characterized by three steps with an overall yield of 71% and a purity or more than 99.0%. This reaction can be scaled up to multikilogram quantities, providing a solid basis for its further bioactivity studies and drug development. With this same method, 6,7,3 ',4 '-tetrahydroxyisoflavanone, an analog of 6,7,4 '-trihydroxyisoflavanone, also can be largely prepared, indicating this modified synthetic method is potentially available for large-scale synthesis of a broad range of multihydroxyl isoflavanones.

  DOI：

  10.1080/00397911.2014.886331

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。
• Antimicrobial and Antioxidant Isoflavonoid Derivatives from the Roots of Amphimas pterocarpoides
  作者：Edwige P. Fodja Saah、Valerie Tedjon Sielinou、Victor Kuete、Stephen T. Lacmata、Augustin E. Nkengfack

  DOI：10.5560/znb.2013-3106

  日期：2013.8.1

  A new bis-isoflavone derivative, named amphiisoflavone (1), was isolated from the roots of Amphimas pterocarpoides, together with three known isoflavones, namely 8-methoxyisoformononetin (2), 6-methoxyisoformononetin (3) and isoformononetin (4). Chemical transformations carried out on compound 3 led to two new derivatives, 4´-acetoxy-6,7-dimethylisoflavone (3a) and 4´-O-prenyl- 6,7-dimethylisoflavone (3p), along with a known compound, 4´,6,7-trimethoxyisoflavone (3m). The structures of all compounds were elucidated from spectroscopic evidence, in particular by 1D and 2D NMR spectroscopic methods. These compounds were evaluated for their antioxidant properties and for their antimicrobial activities against a wide range of bacteria and fungi.

  从紫菀根中分离出一种新的双异黄酮衍生物，命名为双异黄酮（1），以及三种已知的异黄酮，即 8-甲氧基异异异黄酮素（2）、6-甲氧基异异黄酮素（3）和异异黄酮素（4）。通过对化合物 3 进行化学转化，产生了两种新的衍生物，即 4´-乙酰氧基-6,7-二甲基异黄酮（3a）和 4´-O-异戊烯基-6,7-二甲基异黄酮（3p），以及一种已知化合物，即 4´,6,7-三甲氧基异黄酮（3m）。所有化合物的结构都是通过光谱证据，特别是通过一维和二维核磁共振光谱方法阐明的。对这些化合物的抗氧化性以及对多种细菌和真菌的抗菌活性进行了评估。
• Structural modification and antihypertensive activity study of formononetin derivatives
  作者：Sai-Jie Zuo、Dong-Lai Ma、Jing Li、Qiu-Hong Guo、Li Zhou

  DOI：10.1080/10286020.2021.2005588

  日期：2022.9.2
• Inhibitors for expression of IgE receptor on human mast cell from Puerariae Flos
  作者：Satoru Tamura、Kunichika Yoshihira、Mariko Tokumaru、Xu Zisheng、Nobutoshi Murakami

  DOI：10.1016/j.bmcl.2010.05.038

  日期：2010.7

  Bioassay-guided separation of the extract of the medicinal plant, Puerariae Flos, disclosed the two isoflavones tectorigenin (1) and genistein (2) as the inhibitors for expression of IgE receptor (Fc epsilon RI), the key molecule triggering the allergic reactions, on human mast cells. As a result of analysis of structure-activity relationship of the naturally occurring and synthesized isoflavones, 7-O-methyl glycitein (11) was disclosed as the more potent inhibitor than tectorigenin (1). These isoflavone ingredients suppressed expression of FceRI more potently than the active flavonoids found previously. In addition, tectorigenin (1) was clarified to particularly reduce generation of gamma-chain subunit to suppress expression of FceRI among the three subunits. (c) 2010 Elsevier Ltd. All rights reserved.
• ISOFLAVONES AND RELATED COMPOUNDS, METHODS OF PREPARING AND USING AND ANTIOXIDANT COMPOSITIONS CONTAINING SAME
  申请人：Z-L LIMITED PARTNERSHIP

  公开号：EP0027796A1

  公开（公告）日：1981-05-06