1-(2,4-二羟基苯基)-2-(4-羟基苯基)丙-1-酮 | 21255-69-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - α-甲基脱氧安息香黄酮
• 中文名称: 1-(2,4-二羟基苯基)-2-(4-羟基苯基)丙-1-酮
• 英文名称: O-desmethylangolensin
• 英文别名: 1-(2,4-dihydroxyphenyl)-2-(4'-hydroxyphenyl)-1-propanone；1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one；O-demethylangolensin；O-Demethylangolesin；(RS)-O-DMA
• CAS: 21255-69-6
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: JDJPNKPFDDUBFV-UHFFFAOYSA-N

物化性质

• 熔点：
  134-137°C
• 溶解度：
  DMSO（微溶）、Methsnol（微溶）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

ADMET

毒理性

• 毒性总结

O-脱甲基安戈莱辛（ODMA）具有雄激素受体拮抗活性以及对雌激素受体（ER）-α和ERβ的激动活性。ODMA的结构与雌激素相似。（A15413）

O-desmethylangolensin (ODMA) exerts androgen receptor antagonistic activity and agonistic activity towards estrogen receptor (ER)-α and ERβ. The structure of ODMA is somewhat similar to estrogen. (A15413)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2914501900
• 储存条件：
  2-8°C

制备方法与用途

生物活性

O-Desmethylangolensin 是大豆异黄酮在肠道微生物代谢后的产物，具有抗氧化活性。

靶点

Human Endogenous Metabolite

体外研究

O-Desmethylangolensin (O-DMA) 在较高剂量下抑制HepG2细胞的生长（75 μM时约30%的减少）。

反应信息

• 作为反应物：
  描述：

  1-(2,4-二羟基苯基)-2-(4-羟基苯基)丙-1-酮 在 重水 作用下， 以 丙酮 为溶剂， 生成 1-(2,4-di(hydroxy-d)phenyl)-2-(4-(hydroxy-d)phenyl)propan-1-one
  参考文献：
  名称：

  Expedient Deuterolabeling of Polyphenols in Ionic LiquidsDCl/D₂O under Microwave Irradiation

  摘要：

  Postsynthetic regioselective aromatic ring H/D exchanges in polyphenolic compounds are rapidly performed in high yields and isotopic purities in ionic liquidDCl/D2O under microwave irradiation. Other C-H bonds, including benzylic and lactone alpha-carbonyl sites, are not affected.

  DOI：

  10.1021/jo070231p
• 作为产物：
  描述：

  大豆甙元 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以42%的产率得到1-(2,4-二羟基苯基)-2-(4-羟基苯基)丙-1-酮
  参考文献：
  名称：

  α-甲基脱氧安息香素的合成

  摘要：

  在回流的THF中使用LiAlH 4还原羟基和/或甲氧基取代的异黄酮，可轻松获得大量α-甲基脱氧安息香素，可能是人体植物雌激素的代谢产物。的合成Ô -demethylangolensin 2b中，6'- hydroxyangolensin 2C，2D angolensin，1-（2,4-二羟基苯基）-2-苯基丙-1-酮2E，1-（2-羟基-4-甲氧基苯基）-2- （4-羟基苯基）丙烷-1-酮2f，4'- O-甲基血管紧张素2g，1-（2-羟基-4-甲氧基苯基）-2-苯基丙烷-1-酮2h和1-（2-羟基苯基）-描述了2-苯基丙烷-1-酮2i。

  DOI：

  10.1039/a904946k

文献信息

• Catalytic Alkyne Arylation Using Traceless Directing Groups
  作者：Jung‐Woo Park、Bubwoong Kang、Vy M. Dong

  DOI：10.1002/anie.201804955

  日期：2018.10.8

  to generate enamines, which are then hydrolyzed to either α‐arylphenones or α,α‐diarylketones. This Pd‐catalyzed method overcomes established known pathways to enable the use of amines as traceless directing groups for C−C bond formation.

  通过使用 Pd 0 /Mandyphos，我们实现了炔烃的三组分氨基芳基化以生成烯胺，然后将烯胺水解为 α-芳基苯酮或 α,α-二芳基酮。这种 Pd 催化方法克服了已知的已知途径，能够使用胺作为 C−C 键形成的无痕导向基团。
• 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。
• A Versatile Synthesis of O-Desmethylangolensin Analogues from Methoxy-Substituted Benzoic Acids
  作者：Hyo Jeong Hong、Jae In Lee

  DOI：10.5012/jkcs.2014.58.6.569

  日期：2014.12.20

  The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using $Pb(OAc)_4/HClO_4$ in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di-2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-$\alpha}$-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.

  该研究描述了从甲氧基取代的苯甲酸合成 O-去甲基郎格列新（O-DMA）类似物的过程。甲氧基取代的苯甲酸用 2 等量的乙锂处理后得到甲氧基苯丙酮，随后在原甲酸三乙酯中使用 $Pb(OAc)_4/HClO_4$ 通过甲氧基苯基基团的 1,2 重排转化为 2-(甲氧基苯基)丙酸乙酯。用 KOH 进行水解后，2-(甲氧基苯基)丙酸与碳酸二-2-吡啶反应，得到 2-(甲氧基苯基)丙酸 2-吡啶酯，再与甲氧基取代的苯基溴化镁酰化，得到甲氧基-$\alpha}$-甲基去氧苯甲酸酯。使用三溴化硼对这些化合物的甲氧基进行选择性或完全脱甲基化，可以高产率得到多种 O-DMA 类似物。
• THERAPEUTIC METHODS AND COMPOSITIONS INVOLVING ISOFLAVONES
  申请人：KELLY Graham Edmund

  公开号：US20080287528A1

  公开（公告）日：2008-11-20

  Therapeutic methods of treatment, compositions and foodstuffs are described which contain isoflavone compounds described by general formula (1), in which Z is H, R 1 is H, or R A CO where R A is C 1-10 alkyl or an amino acid, R 2 is H, OH, or OR B where R B is an amino acid, or COR A where R A is as previously defined, W is H, A is H or OH, and B is selected from (a), (b), (c), or W is H, and A and B taken together form a six-membered ring selected from (d), or W, A and B taken with the groups with which they are associated comprise (e), or W and A taken together with the groups with which they are associated comprise (f) and B is (g) wherein R 3 is H, COR A where R A is as previously defined, CO 2 R C where R C is C 1-10 alkyl, or COR B where R B is as previously defined, R 4 is H, COR D where R D is H, OH, C 1-10 alkyl or an amino acid, CO 2 R C where R C is as previously defined, COR E where R E is H, C 1-10 alkyl or an amino acid, COOH, COR C where R C is as previously defined, or CONHR E where R E is as previously defined, R 5 is H, CO 2 R C where R C is as previously defined, or COR C OR E where R C and R E are as previously defined, and where the two R 5 groups are attached to the same group they are the same or different, R 6 is H or hydroxy C 1-10 alkyl, X is preferably O, but may be N or S, and Y is (h) where R 7 is H, or C 1-10 alkyl.

  本文描述了治疗方法、组合物和食品，其中包含一般式（1）所描述的异黄酮化合物，其中Z为H，R1为H或RACO，其中RA为C1-10烷基或氨基酸，R2为H、OH或ORB，其中RB为氨基酸，或CORA，其中RA如先前定义，W为H，A为H或OH，B选自（a）、（b）、（c），或W为H，A和B结合形成六元环，选自（d），或W、A和B与它们相关的基团组成（e），或W和A与它们相关的基团组成（f），B为（g），其中R3为H，CORA，其中RA如先前定义，CO2RC，其中RC为C1-10烷基，或CORB，其中RB如先前定义，R4为H，CORD，其中RD为H、OH、C1-10烷基或氨基酸，或CO2RC，其中RC如先前定义，CORE，其中RE为H、C1-10烷基或氨基酸，或COOH，CORC，其中RC如先前定义，或CONHRE，其中RE如先前定义，R5为H，CO2RC，其中RC如先前定义，或CORCORE，其中RC和RE如先前定义，且当两个R5基团连接到同一基团时，它们相同或不同，R6为H或羟基C1-10烷基，X优选为O，但也可以为N或S，Y为（h），其中R7为H或C1-10烷基。
• Therapeutic methods and compositions involving isoflavones
  申请人：Novogen Research Pty. Ltd.

  公开号：EP1927352A2

  公开（公告）日：2008-06-04

  Therapeutic methods of treatment, compositions and foodstuffs are described which contain isoflavone compounds described bathe general formula I in which Z is H, R1 is H, or RACO where RA is C1-10 alkyl or an amino acid, R2 is H, OH, or ORB where RB is an amino acid or CORA where RA is as previously defined, W is H, A is H or OH, and B is selected from or W is H, and A, and B taken together form a six membered ring selected from or W, A and B taken with the groups with which they are associated comprise or W and A taken together with the groups with which they are associated comprise and B is wherein R3 is H, CORA where RA is as previously defined , CO2RC where RC is C1-10 alkyl, or CORB where RB, is as previously defined, R4 is H, CORD where RD is H, OH, C1-10 alkyl or an amino acid, CO2RC where RC is as previously defined, CORE where RE is H, C1-10 alkyl or an amino acid, COOH, CORC where RC is as previously defined, or CONHRE where RE is as previously defined, R5 is H, CO2RC where RC is as previously defined, or CORCORE where RC and RE are as previously defined, and where the two R5 groups are attached to the same group they are the same or different, R6 is H or hydroxy C1-10 alkyl, X is preferably O, but may be N or S, and Y is where R7 is H, or C1-10 alkyl.

  描述了含有通式 I 所述异黄酮化合物的治疗方法、组合物和食品 其中 Z 是 H R1 是 H 或 RACO，其中 RA 是 C1-10 烷基或氨基酸、 R2 是 H、OH 或 ORB（其中 RB 是氨基酸）或 CORA（其中 RA 如前定义、 W 是 H，A 是 H 或 OH，B 选自 或 W 是 H，A 和 B 共同形成一个选自以下各项的六员环 或 W、A 和 B 与它们相关联的基团组成 或 W 和 A 连同与之有关联的组构成 而 B 是 其中 R3 是 H、RA 如前定义的 CORA、RC 是 C1-10 烷基的 CO2RC 或 RB 如前定义的 CORB、 R4 是 H、RD 为 H、OH、C1-10 烷基或氨基酸的 CORD、RC 如前定义的 CO2RC、RE 为 H、C1-10 烷基或氨基酸的 CORE、COOH、RC 如前定义的 CORC 或 RE 如前定义的 CONHRE、 R5 为 H，RC 如前定义的 CO2RC，或 CORCORE，其中 RC 和 RE 如前定义，当两个 R5 基团连接到同一基团上时，它们是相同的或不同的、 R6 是 H 或羟基 C1-10 烷基、 X 最好是 O，但也可以是 N 或 S，以及 Y 是 其中 R7 是 H 或 C1-10 烷基。