2-(3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone | 111474-27-2

• 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-(3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone
• 英文别名: 2,4,6-trihydroxy-3'-methoxydeoxybenzoin；2,4,6-trihydroxy-3'-methoxy-deoxybenzoin；2,4,6-Trihydroxy-3'-methoxy-desoxybenzoin
• CAS: 111474-27-2
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: GZUWLVIEMWPACV-UHFFFAOYSA-N

物化性质

• 熔点：
  168–169°C
• 沸点：
  475.3±14.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone 在 potassium carbonate 、 丙酮 作用下， 生成 4-acetoxy-5,7-dimethoxy-3-(3-methoxy-phenyl)-coumarin
  参考文献：
  名称：

  Gilbert et al., Journal of the Chemical Society, 1957, p. 3740,3745

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 2-(3-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)ethanone
  参考文献：
  名称：

  Synthesis and Evaluation of Derrubone and Select Analogues

  摘要：

  [GRAPHICS]Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.

  DOI：

  10.1021/jo702366g

文献信息

• Free-Radical-Scavenging, Antityrosinase, and Cellular Melanogenesis Inhibitory Activities of Synthetic Isoflavones
  作者：Tzy-Ming Lu、Horng-Huey Ko、Lean-Teik Ng、Yen-Pin Hsieh

  DOI：10.1002/cbdv.201400208

  日期：2015.6

  potential of synthetic isoflavones for application in cosmeceuticals. Twenty‐five isoflavones were synthesized and their capacities of free‐radical‐scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further

  在这项研究中，我们研究了合成异黄酮在药妆品中的应用潜力。合成了 25 种异黄酮，并评估了它们清除自由基和抑制蘑菇酪氨酸酶的能力，以及它们对 B16F10 鼠黑色素瘤细胞和 HaCaT 人角质形成细胞的细胞活力的影响。进一步研究了显示出显着蘑菇酪氨酸酶抑制活性的异黄酮在体外 B16F10 黑素细胞中减少细胞黑色素形成和抗酪氨酸酶活性。在测试的异黄酮中，6-羟基黄豆苷元 (2) 是 ABTS.+ 和 DPPH 的最强清除剂。SC50 值分别为 11.3±0.3 和 9.4±0.1 μM 的自由基。Texasin (20) 表现出最有效的蘑菇酪氨酸酶抑制作用 (IC50 14.9±4.5 μM)，而 retusin (17) 分别显示出对 B16F10 黑素细胞中细胞黑色素形成和抗酪氨酸酶活性的最有效抑制。总之，retusin (17) 和 texasin (20) 都表现出强大的自由基清除能力
• Synthesis of isoflavones via base catalysed condensation reaction of deoxybenzoin
  作者：Wanmei Li、Fangming Liu、Pengfei Zhang

  DOI：10.3184/030823408x382135

  日期：2008.12

  Base catalysed condensation reaction of o-hydroxyl-α-phenylacetophenones with formyl reagents affords various substituted isoflavones. Many bases were tested in the condensation reaction and DMAP was found to be the most effective catalysis.

  邻羟基-α-苯基苯乙酮与甲酰基试剂的碱催化缩合反应得到各种取代的异黄酮。在缩合反应中测试了许多碱，发现 DMAP 是最有效的催化作用。
• Synthesis and Structure−Activity Relationship Study of Deoxybenzoins on Relaxing Effects of Porcine Coronary Artery
  作者：Tzy-Ming Lu、Daih-Huang Kuo、Horng-Huey Ko、Lean-Teik Ng

  DOI：10.1021/jf1023643

  日期：2010.9.22

  Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC(50) = 3.30 mu M (E(max) = 100%, n = 7) and 2,4-dihydroxy-4'-methoxydeoxybenzoin EC(50) = 3.70 mu M (E(max) = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H >= p-OMe > p-OH > o-OMe > m,p-diOMe >= m-OMe.
• Synthesis and Evaluation of Derrubone and Select Analogues
  作者：Jedidiah M. Hastings、M. Kyle Hadden、Brian S. J. Blagg

  DOI：10.1021/jo702366g

  日期：2008.1.1

  [GRAPHICS]Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.
• Gilbert et al., Journal of the Chemical Society, 1957, p. 3740,3745
  作者：Gilbert et al.

  DOI：——

  日期：——