6,7,4'-三羟基异黄烷 | 94105-89-2

• 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: 6,7,4'-三羟基异黄烷
• 英文名称: (+/-)-6-Hydroxy-Equol
• 英文别名: 6,7,4'-trihydroxyisoflavan；HIR-1；3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-6,7-diol
• CAS: 94105-89-2
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: NLIIKGCVOJPMQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对羟基苯乙腈 在 盐酸 、 硫酸 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 水 、 甲基磺酰氯 、 zinc(II) chloride 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 6,7,4'-三羟基异黄烷
  参考文献：
  名称：

  Enzymatic Studies of Isoflavonoids as Selective and Potent Inhibitors of Human Leukocyte 5-Lipo-Oxygenase

  摘要：

  Continuing our search to find more potent and selective 5‐LOX inhibitors, we present now the enzymatic evaluation of seventeen isoflavones (IR) and nine isoflavans (HIR), and their in vitro and in cellulo potency against human leukocyte 5‐LOX. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5‐LOX (IR‐2, HIR‐303, and HIR‐309), with IC50 values at least 10 times lower than those of 12‐LOX, 15‐LOX‐1, and 15‐LOX‐2. Of these three, IR‐2 (6,7‐dihydroxy‐4‐methoxy‐isoflavone, known as texasin) was the most selective 5‐LOX inhibitor, with over 80‐fold potency difference compared with other isozymes; Steered Molecular Dynamics (SMD) studies supported these findings. The presence of the catechol group on ring A (6,7‐dihydroxy versus 7,8‐dihydroxy) correlated with their biological activity, but the reduction of ring C, converting the isoflavones to isoflavans, and the substituent positions on ring B did not affect their potency against 5‐LOX. Two of the most potent/selective inhibitors (HIR‐303 and HIR‐309) were reductive inhibitors and were potent against 5‐LOX in human whole blood, indicating that isoflavans can be potent and selective inhibitors against human leukocyte 5‐LOX in vitro and in cellulo.

  DOI：

  10.1111/cbdd.12469

文献信息

• ISOFLAVONE METABOLITES
  申请人：Joannou George Eustace

  公开号：US20080125481A1

  公开（公告）日：2008-05-29

  There are disclosed compounds of formulae (I) or (II) in which A is selected from the group consisting of (1), (2), (3) and (4); OH, and one of R 1 and R 2 is selected from H, OH and OCH 3 , and the other of R 1 and R 2 is selected from OH and OCH 3 ; one of R3 and R4 is selected from H, OH and OCH3, and the other of R3 and R4 is selected from OH and OCH3; provided that at least one of the pairs R 1 , R 2 and R 3 , R 4 are both OH; R 5 is selected from OH and OCH 3 ; and denotes a single or double bond; and pharmaceutically acceptable salts and prodrugs thereof. The compounds of the invention are useful for the treatment of hormone-dependent conditions and cancers.

  公开了式（I）或（II）的化合物，其中A从（1），（2），（3）和（4）组成的群体中选择；OH，R1和R2中的一个选择自H，OH和OCH3，另一个选择自OH和OCH3；R3和R4中的一个选择自H，OH和OCH3，另一个选择自OH和OCH3；前提是R1，R2和R3，R4中至少有一对是OH；R5选择自OH和OCH3；并表示单键或双键；以及其药学上可接受的盐和前药。本发明的化合物用于治疗激素依赖性疾病和癌症。
• Topical formulations and methods of use
  申请人：Morariu Marius

  公开号：US20060216251A1

  公开（公告）日：2006-09-28

  A topical composition comprising a lipoic acid, a carnitine, and a carnosine in a suitable vehicle for topical application and a method for treating skin is provided. The present compositions are useful in improving the appearance of aged skin characterized by wrinkles and loss of elasticity. Preferred components include R-lipoic acid or R-dihydrolipoic acid, acetyl-1-carnitine, and 1-carnosine.

  本发明提供了一种外用组合物，该组合物包含硫辛酸、肉毒碱和肉毒碱，并以适合外用的载体形式存在，还提供了一种治疗皮肤的方法。本组合物有助于改善以皱纹和失去弹性为特征的老化皮肤的外观。优选成分包括 R-硫辛酸或 R-二氢硫辛酸、乙酰基-1-肉碱和 1-肉碱。
• Structure–activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2
  作者：Yesseny Vasquez-Martinez、Rachana V. Ohri、Victor Kenyon、Theodore R. Holman、Silvia Sepúlveda-Boza

  DOI：10.1016/j.bmc.2007.07.036

  日期：2007.12

  Human lipoxygenase (hLO) isozymes have been implicated in a number of disease states and have attracted much attention with respect to their inhibition. One class of inhibitors, the flavonoids, have been shown to be potent lipoxygenase inhibitors but their study has been restricted to those compounds found in nature, which have limited structural variability. We have therefore carried out a comprehensive study to determine the structural requirements for flavonoid potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2. We conclude from this study that catechols are essential for high potency, that isoflavones and isoflavanones tend to select against 12-hLO, that isoflavans tend to select against 15-hLO-1, but few flavonoids target 15-hLO-2. (C) 2007 Elsevier Ltd. All rights reserved.
• Phenyl-benzyl-ketones
  申请人：Ruane, Michael

  公开号：EP1743881B1

  公开（公告）日：2010-12-22
• COMPOSITIONS FOR PROLIFERATION OF CELLS AND RELATED METHODS
  申请人：The Hospital For Sick Children

  公开号：EP2598150A2

  公开（公告）日：2013-06-05