2-(3-bromophenyl)-2,3-dihydro-5,7-dihydroxychromen-4-one | 120980-78-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3-bromophenyl)-2,3-dihydro-5,7-dihydroxychromen-4-one
• 英文别名: (+/-)-5,7-dihydroxy-3'-bromo-flavanone；3'-bromo-5,7-dihydroxyflavanone；PTP inhibitor, 4i；2-(3-bromophenyl)-5,7-dihydroxy-2,3-dihydrochromen-4-one
• CAS: 120980-78-1
• 化学式: C₁₅H₁₁BrO₄
• 分子量: 335.154
• InChiKey: NYKQDHRWOHMWTF-UHFFFAOYSA-N

物化性质

• 熔点：
  217-218 °C
• 沸点：
  545.5±50.0 °C(Predicted)
• 密度：
  1.667±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  2-(3-bromophenyl)-2,3-dihydro-5,7-dihydroxychromen-4-one 在 吡啶 、 碘 作用下， 反应 4.0h， 以50%的产率得到2-(3-bromophenyl)-5,7-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of flavone derivatives as potential radioligands for imaging the multidrug resistance-associated protein 1 (ABCC1/MRP1)

  摘要：

  Multidrug resistance (MDR) is one of the major problems affecting the treatment of cancer. In vivo visualization and quantification of MDR proteins would be of great value to better select the therapeutic strategy. Six flavone-based compounds were synthesized and evaluated for their cytotoxic activity and MDR-reversing capacity using hMRP1 or hMDR1 overexpressing cell lines for in vitro assays. All the flavone derivatives were highly selective for hMRP1-expressing cell lines. These derivatives each used at 4 mu M (a non-cytotoxic concentration) enhance significantly the sensitivity of hMRP1-mediated MDR cell line toward doxorubicin toxicity. Their MDR-reversing capacity suggests that, in particular, the 4'-fluoroalkyloxy and 4'-iodo apigenin derivatives are potential new radiopharmaceuticals to visualize in vivo MRP1-mediated MDR phenomenon by PET or SPECT. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.009
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 盐酸 、 sodium acetate 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-(3-bromophenyl)-2,3-dihydro-5,7-dihydroxychromen-4-one
  参考文献：
  名称：

  甘草素衍生物抗阿尔茨海默病活性的设计、合成和胆碱酯酶抑制试验

  摘要：

  海洋环境是发现功能材料的丰富资源，海藻因其在生物学和医学中的潜在用途而受到认可。甘草素已从马尾藻中分离和鉴定。为了寻找新的抗阿尔茨海默病活性，我们设计并合成了 32种 7-异戊二烯氧基-2,3-二氢黄烷酮衍生物 ( 3a-3p ) 和 5-羟基-7-异戊二烯氧基-2,3-二氢黄烷酮衍生物 ( 4a- 4p）作为基于甘草素作为先导化合物的胆碱酯酶抑制剂。对乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 的抑制筛选表明，所有合成的化合物在体外均具有有效的 AChE 抑制活性，但对 BuChE 的抑制活性减弱至较弱. 动力学研究表明，化合物 4o 通过双重结合位点能力抑制 AChE。此外，所有化合物均显示出自由基清除作用。最后，4o在AChE活性位点的分子对接模拟与所得药理结果吻合较好。

  DOI：

  10.1016/j.bmcl.2021.128306

文献信息

• Zhao, Dong-Hai; Sui, Xin; Qu, You-Le, Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1129 - 1132
  作者：Zhao, Dong-Hai、Sui, Xin、Qu, You-Le、Yang, Li-Ye、Wang, Xian、Guan, Li-Ping

  DOI：——

  日期：——
• Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents
  作者：Xiaowu Dong、Tao Liu、Jingying Yan、Peng Wu、Jing Chen、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.11.052

  日期：2009.1

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.