3,4-methylenedioxybenzyl 2,4,5-trihydroxyphenyl ketone | 2828-14-0

• 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: 3,4-methylenedioxybenzyl 2,4,5-trihydroxyphenyl ketone
• 英文别名: 2-benzo[1,3]dioxol-5-yl-1-(2,4,5-trihydroxy-phenyl)-ethanone；<2,4,5-Trihydroxy-phenyl>-piperonyl-keton；2-(2H-1,3-Benzodioxol-5-yl)-1-(2,4,5-trihydroxyphenyl)ethan-1-one；2-(1,3-benzodioxol-5-yl)-1-(2,4,5-trihydroxyphenyl)ethanone
• CAS: 2828-14-0
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: NSDUEFZDVJMSMH-UHFFFAOYSA-N

物化性质

• 熔点：
  206–208°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-methylenedioxybenzyl 2,4,5-trihydroxyphenyl ketone 生成 3,4-methylenedioxybenzyl 2-hydroxy-4,5-dimethoxyphenyl ketone
  参考文献：
  名称：

  JAIN, AMOLAK C.;PRASAD, ASHOK K., INDIAN J. CHEM. B, 27,(1988) N 7, C. 622-624

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-苯并二氧杂环戊烯-5-乙腈 在 盐酸 、 zinc(II) chloride 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 生成 3,4-methylenedioxybenzyl 2,4,5-trihydroxyphenyl ketone
  参考文献：
  名称：

  Jain, Amolak C.; Prasad, Ashok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 622 - 624

  摘要：

  DOI：

文献信息

• 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.
• Enzymatic Studies of Isoflavonoids as Selective and Potent Inhibitors of Human Leukocyte 5-Lipo-Oxygenase
  作者：Carolina Mascayano、Victoria Espinosa、Silvia Sepúlveda-Boza、Eric K. Hoobler、Steve Perry、Giovanni Diaz、Theodore R. Holman

  DOI：10.1111/cbdd.12469

  日期：2015.7

  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.
• ISOFLAVANS DERIVATIVES AS INHIBITORS OF SOYBEAN LIPOXYGENASE: IN-VITRO AND DOCKING STUDIES
  作者：CAROLINA MASCAYANO、MARCOS CAROLI REZENDE、YENIFER RIVERA、VICTORIA ESPINOSA

  DOI：10.4067/s0717-97072011000400024

  日期：——

  The lipoxygenases (LOX) are a family of non-heme iron-containing dioxygenases which catalyze the stereospecific insertion of molecular oxygen lino arachidonic acid, leading to hydroxy derivatives as end products. In this work, we studied the behavior of seven isoflavans on 15-soybean lipoxygenases (15-sLOX), comparing them with the known inhibitors quercetin and 3,4-dihydroxybenzoic acid. Four of the seven investigated isoflavans showed IC50 values smaller than 50 mu M, being more potent than quercetin or 3, 4-dihydroxybenzoic acid. Besides a catecholic pattern, the presence of an aromatic ring B seems to confer additional activity to these compounds, a result which was rationalized by docking studies of these isoflavanss into the enzyme binding site.
• JAIN, AMOLAK C.;PRASAD, ASHOK K., INDIAN J. CHEM. B, 27,(1988) N 7, C. 622-624
  作者：JAIN, AMOLAK C.、PRASAD, ASHOK K.

  DOI：——

  日期：——
• Jain, Amolak C.; Prasad, Ashok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 622 - 624
  作者：Jain, Amolak C.、Prasad, Ashok K.

  DOI：——

  日期：——