2,4,4'-trihydroxy-3-methyldeoxybenzoin | 139256-03-4

• 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: 2,4,4'-trihydroxy-3-methyldeoxybenzoin
• 英文别名: 1-(2,4-dihydroxy-3-methyl-phenyl)-2-(4-hydroxy-phenyl)-ethanone；1-(2,4-dihydroxy-3-methylphenyl)-2-(4-hydroxyphenyl)ethanone
• CAS: 139256-03-4
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: GKDAKFMLTZJTDY-UHFFFAOYSA-N

物化性质

• 熔点：
  187–188°C
• 沸点：
  514.0±19.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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

反应信息

• 作为反应物：
  描述：

  2,4,4'-trihydroxy-3-methyldeoxybenzoin 在 三氟化硼乙醚 、 甲基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.15h， 以66%的产率得到7-hydroxy-3-(4-hydroxyphenyl)-8-methyl-4H-chromen-4-one
  参考文献：
  名称：

  [EN] SUBSTITUTED CHROMAN DERIVATIVES, MEDICAMENTS AND USE IN THERAPY
  [FR] DÉRIVÉS DE CHROMANE SUBSTITUÉS, MÉDICAMENTS ET UTILISATION À DES FINS THÉRAPEUTIQUES

  摘要：

  描述了新型替代色呐衍生物和中间化合物、含有这些化合物的组合物、其制备方法以及作为治疗剂的用途，特别是作为抗癌和化疗选择性剂。

  公开号：

  WO2006032085A1
• 作为产物：
  描述：

  对羟基苯乙腈 在 盐酸 、 水 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 生成 2,4,4'-trihydroxy-3-methyldeoxybenzoin
  参考文献：
  名称：

  异黄酮和异黄酮作为人类12和15脂氧合酶的强抑制剂的体外研究

  摘要：

  在这项研究中，我们研究了16种异黄酮和异黄酮衍生物作为人类脂氧合酶的潜在抑制剂（血小板12-脂氧合酶，网状细胞15-脂氧合酶-1和上皮15-脂氧合酶-2）。类黄酮黄ical素（一种已知的脂加氧酶抑制剂）用作阳性对照。四种化合物，6,7-二羟基-3'-氯异黄酮（1c），7-羟基-8-甲基-4'-氯异黄酮（5a），7,8-二羟基-4'-甲基异黄酮（5b）和7， 8-dihydroxy-3'methylisoflavan（5c）是有效的12-lipoxygenases和15-lipoxygenase-1的抑制剂，IC 50小于10μm，而6,7-dihydroxy-4-4'-nitroisoflavone（1b）是12-脂氧合酶的选择性抑制剂。对三种最佳抑制剂（1b，5b，5c）进行了对接研究，抗氧化剂测定和动力学测量。结果表明，环A中的邻苯二酚基团对于这些化合物的抗氧化性能至关重要，并且可能对

  DOI：

  10.1111/cbdd.12157

文献信息

• Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
  作者：Jianzhuang Miao、Huaqing Cui、Jing Jin、Fangfang Lai、Hui Wen、Xiang Zhang、Gian Filippo Ruda、Xiaoguang Chen、Dali Yin

  DOI：10.1039/c4cc06762b

  日期：——

  A new class of fluorophores 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) is developed and is suitable as reagents for biological imaging.

  一种新型荧光物质3-烷基-6-甲氧基-7-羟基-香豆素（AMHCs）已开发，并适用于生物成像试剂。
• Substituted chroman derivatives, medicaments and use in therapy
  申请人：Heaton Andrew

  公开号：US20060074127A1

  公开（公告）日：2006-04-06

  Novel substituted chroman derivatives and intermediate compounds, compositions containing same, methods for their preparation and uses thereof as therapeutic agents particularly as anti-cancer and chemotherapeutic selective agents are described.

  本发明涉及一种替代的色满衍生物及其中间化合物、含有它们的组合物、制备它们的方法以及它们作为治疗剂的用途，特别是作为抗癌和化学治疗选择性剂。
• SUBSTITUTED CHROMAN DERIVATIVES, MEDICAMENTS AND USE IN THERAPY
  申请人：HEATON Andrew

  公开号：US20090317490A1

  公开（公告）日：2009-12-24

  Novel substituted chroman derivatives and intermediate compounds, compositions containing same, methods for their preparation and uses thereof as therapeutic agents particularly as anti-cancer and chemotherapeutic selective agents are described.

  本发明描述了代替的色甘醇衍生物和中间化合物，包含它们的组合物，制备它们的方法以及它们作为治疗剂的用途，特别是作为抗癌和化学治疗选择性剂。
• 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.
• Waehaelae, Kristiina; Hase, Tapio A., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3005 - 3008
  作者：Waehaelae, Kristiina、Hase, Tapio A.

  DOI：——

  日期：——