7-(4-bromobutoxy)-2-phenyl-4H-1-benzopyran-4-one

• 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: 7-(4-bromobutoxy)-2-phenyl-4H-1-benzopyran-4-one
• 英文别名: 7-(4-bromobutoxy)-2-phenyl-4H-chromen-4-one；7-(4-Bromobutoxy)-2-phenylchromen-4-one
• 化学式: C₁₉H₁₇BrO₃
• 分子量: 373.246
• InChiKey: UBDSWVPDDXXAJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-4-硝基咪唑 、 7-(4-bromobutoxy)-2-phenyl-4H-1-benzopyran-4-one 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 17.0h， 以62%的产率得到7-(4-(2-methyl-5-nitro-1H-imidazol-1-yl)butoxy)-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  新型偶氮基黄酮的设计，合成及其对蛋白酪氨酸磷酸酶-1B的抑制活性

  摘要：

  合成了一系列偶氮基黄酮，并通过NMR，IR，MS和HRMS光谱进行了表征。筛选所有新制备的化合物潜在的蛋白酪氨酸磷酸酶抑制活性。生物活性测定表明，大多数偶氮基黄酮类化合物均具有良好的蛋白磷酸酶1B（PTP1B）抑制活性。特别是，三唑基黄酮6a表现出最好的抑制活性（IC 50  = 1.6μM），对PTP1B的选择性是与密切相关的T细胞蛋白酪氨酸磷酸酶（TCPTP）的9.9倍。细胞活力测定表明6a具有较低的细胞毒性。分子建模和动力学研究揭示了PTP1B相对于TCPTP选择性的原因。对这些化合物进行了量子化学研究，以了解活性必不可少的结构特征。

  DOI：

  10.1016/j.bioorg.2018.06.008
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 碘 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 76.75h， 生成 7-(4-bromobutoxy)-2-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Chromone derivatives bearing pyridinium moiety as multi-target-directed ligands against Alzheimer’s disease

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104750

文献信息

• Synthesis and Cytotoxic Evaluation of Potential Bis-Intercalators: Tetramethylenebis(oxy)- and Hexamethylenebis(oxy)-Linked Assemblies Consisting of Flavone, Xanthone, Anthraquinone, and Dibenzofuran
  作者：Tai-Chi Wang、Yue-Ling Zhao、Shorong-Shii Liou

  DOI：10.1002/1522-2675(200205)85:5<1382::aid-hlca1382>3.0.co;2-y

  日期：2002.5

  In a search for potential inhibitors of solid-tumor growth. certain alkanediylbis(oxy)-linked assemblies were synthesized kind evaluated for their cytotoxicity as bis-intercalators. Symmetrical assemblies 1b-12b were synthesized front their respective Aryl-OH and either dibromobutane or dibromohexane, while unsymmetrical ones 13-15 were prepared front Aryl(1)-OH and either Aryl(2)-O-(CH2)(4)Br or Aryl(2)-O-(CH2)(6)Br. These bis-intercalators were inactive against the growth of leukemia cells. However, some of them were active against the growth of certain solid tumors such as HOP-62, HOP-92 (non-small-cell lung cancer), SF-265, SNB-75, U251 (CNS cancer), A498 (renal cancer), and HS578T (breast cancer). Among them, [hexane-1,6-diylbis(oxy)bis(4,1-phenylene)]bis[4H-1-benzopyran] (6b) was especially active against the growth of all CNS cancer cell lines and also the growth of A498, HOP-62, and HOP-92 with GI(50) values of 17.0. 20.0, and 21.8 mum, respectively.
• Multifunctional tacrine–flavonoid hybrids with cholinergic, β-amyloid-reducing, and metal chelating properties for the treatment of Alzheimer's disease
  作者：Su-Yi Li、Xiao-Bing Wang、Sai-Sai Xie、Neng Jiang、Kelvin D.G. Wang、He-Quan Yao、Hong-Bin Sun、Ling-Yi Kong

  DOI：10.1016/j.ejmech.2013.09.024

  日期：2013.11

  A new series of tacrine flavonoid hybrids (13a u) had been designed, synthesized, and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). In vitro studies showed that most of the molecules exhibited a significant ability to inhibit ChE and self-induced amyloid-beta (A beta(1-42)) aggregation. Kinetic and molecular modeling studies also indicated compounds were mixed-type inhibitors, binding simultaneously to active, peripheral and mid-gorge sites of AChE. Particularly, compound 13k was found to be highly potent and showed a balanced inhibitory profile against ChE and self-induced A beta(1-42) aggregation. Moreover, it also showed excellent metal chelating property and low cell toxicity. These results suggested that 13k might be an excellent multifunctional agent for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and biological evaluation of new arylpiperazine derivatives bearing a flavone moiety as α1-adrenoceptor antagonists
  作者：Jing Jin、Xiao-Bing Wang、Ling-Yi Kong

  DOI：10.1016/j.bmcl.2010.12.080

  日期：2011.2

  Elaborate study on the three-dimensional model of alpha(1)-adrenoceptor (alpha(1)-AR) antagonists led to the development of a series of new arylpiperazine derivatives bearing a flavone nucleus as alpha(1)-AR antagonists. The in vitro activities were evaluated and compounds 1, 4, 10, 13 and 15 showed activities close to the reference compound (Prazosin). (C) 2010 Elsevier Ltd. All rights reserved.
• Design, synthesis of novel azolyl flavonoids and their protein tyrosine Phosphatase-1B inhibitory activities
  作者：Ling Zhang、Yu Ge、Hao Ming Song、Qing Ming Wang、Cheng-He Zhou

  DOI：10.1016/j.bioorg.2018.06.008

  日期：2018.10

  A series of azolyl flavonoids were synthesized and characterized by NMR, IR, MS and HRMS spectra. All the newly prepared compounds were screened for their potential protein tyrosine phosphatase inhibitory activities. Bioactive assay manifested that most of the azolyl flavonoids exhibited good protein phosphatase 1B (PTP1B) inhibitory activities. Especially, triazolyl flavonoid 6a displayed the best

  合成了一系列偶氮基黄酮，并通过NMR，IR，MS和HRMS光谱进行了表征。筛选所有新制备的化合物潜在的蛋白酪氨酸磷酸酶抑制活性。生物活性测定表明，大多数偶氮基黄酮类化合物均具有良好的蛋白磷酸酶1B（PTP1B）抑制活性。特别是，三唑基黄酮6a表现出最好的抑制活性（IC 50  = 1.6μM），对PTP1B的选择性是与密切相关的T细胞蛋白酪氨酸磷酸酶（TCPTP）的9.9倍。细胞活力测定表明6a具有较低的细胞毒性。分子建模和动力学研究揭示了PTP1B相对于TCPTP选择性的原因。对这些化合物进行了量子化学研究，以了解活性必不可少的结构特征。
• Chromone derivatives bearing pyridinium moiety as multi-target-directed ligands against Alzheimer’s disease
  作者：Shahin Abdpour、Leili Jalili-Baleh、Hamid Nadri、Hamid Forootanfar、Syed Nasir Abbas Bukhari、Ali Ramazani、Seyed Esmaeil Sadat Ebrahimi、Alireza Foroumadi、Mehdi Khoobi

  DOI：10.1016/j.bioorg.2021.104750

  日期：2021.5