3,4-dihydroxy-4'-methoxydeoxybenzoin | 1241384-46-2

• 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: 3,4-dihydroxy-4'-methoxydeoxybenzoin
• 英文别名: 3,4-Dihydroxy-4''-methoxydeoxybenzoin；1-(3,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone
• CAS: 1241384-46-2
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: KMELECLHMVZXAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dihydroxy-4'-methoxydeoxybenzoin 、 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylbenzenesulfonate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 以81%的产率得到1-(3-hydroxy-4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)-2-(4-methoxyphenyl)ethanone
  参考文献：
  名称：

  甲硝唑-脱氧安息香衍生物作为抗幽门螺杆菌药物，对HPE诱导的白介素-8具有强抑制活性

  摘要：

  合成了一系列新的甲硝唑-脱氧安息香衍生物，并评估了它们对幽门螺杆菌的抗菌活性。在合成的化合物中还观察到了高度选择性的抗幽门螺杆菌活性。与阳性对照阿莫西林相似，化合物34显示出最有效的活性。此外，化合物17和34能够显着降低幽门螺杆菌水提取物（HPE）诱导的胃粘膜细胞白细胞介素8（IL-8）的产生，但对细胞活力没有任何影响。

  DOI：

  10.1002/cmdc.201000126
• 作为产物：
  描述：

  对甲氧基苯乙酸 、 邻苯二酚 在 三氟化硼乙醚 作用下， 反应 2.0h， 以66.7%的产率得到3,4-dihydroxy-4'-methoxydeoxybenzoin
  参考文献：
  名称：

  甲硝唑-脱氧安息香衍生物作为抗幽门螺杆菌药物，对HPE诱导的白介素-8具有强抑制活性

  摘要：

  合成了一系列新的甲硝唑-脱氧安息香衍生物，并评估了它们对幽门螺杆菌的抗菌活性。在合成的化合物中还观察到了高度选择性的抗幽门螺杆菌活性。与阳性对照阿莫西林相似，化合物34显示出最有效的活性。此外，化合物17和34能够显着降低幽门螺杆菌水提取物（HPE）诱导的胃粘膜细胞白细胞介素8（IL-8）的产生，但对细胞活力没有任何影响。

  DOI：

  10.1002/cmdc.201000126

文献信息

• Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins
  作者：Lean-Teik Ng、Horng-Huey Ko、Tzy-Ming Lu

  DOI：10.1016/j.bmc.2009.05.019

  日期：2009.7

  Deoxybenzoins (DOBs) are one-pot synthetic precursors of isoflavones with feature analogous to those beneficial polyphenols such as resveratrol (stilbene) and phloretin (dihydrochalcone). In this study, seventeen polyphenolic DOBs were synthesized and evaluated by various antioxidant assays and tyrosinase inhibitory effect in vitro. Results displayed that these DOBs are powerful antioxidants; for example, 2,3,4-trihydroxy-3',4'-dimethoxydeoxybenzoin possesses an excellent anti-lipid peroxidation activity (IC50 = 0.72 +/- 0.16 mu M), whilst 2,4,4',5-tetrahydroxydeoxybenzoin showed good DPPH radical scavenging activity (IC50 = 0.69 +/- 0.04 mu M), which were better than Trolox and vitamin C. Besides exhibiting a weak metal chelating effect, these DOBs were effective in scavenging ABTS(center dot+) and superoxide anion (O-2(center dot-)) radicals. DOBs also exhibited potent mushroom tyrosinase inhibitory activity; for example 2,3,4'-trihydroxy4- methoxydeoxybenzoin displayed stable and significant inhibitory effect on tyrosinase activity, with IC50 values 43.37, 43.10 and 46.10 mu M at incubation intervals of 0.5, 1.5, and 2.5 h, respectively. These results suggest that, with the advantage of being readily synthesizable small molecules, DOBs can be potentially developed into clinical and industrial antioxidants. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.
• 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.