7-(3-bromopropoxy)-2-phenyl-4H-chromen-4-one | 191936-16-0

• 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-(3-bromopropoxy)-2-phenyl-4H-chromen-4-one
• 英文别名: 7-(3-Bromopropoxy)-2-phenylchromen-4-one
• CAS: 191936-16-0
• 化学式: C₁₈H₁₅BrO₃
• 分子量: 359.219
• InChiKey: MPKNTUNOHDJYMM-UHFFFAOYSA-N

物化性质

• 沸点：
  505.8±50.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-(4-甲基苯基)哌嗪 、 7-(3-bromopropoxy)-2-phenyl-4H-chromen-4-one 以 甲苯 为溶剂， 反应 48.0h， 以23.7%的产率得到7-[3-[4-(4-Methylphenyl)piperazin-1-yl]propoxy]-2-phenylchromen-4-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new arylpiperazine derivatives bearing a flavone moiety as α1-adrenoceptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.12.080
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.77h， 生成 7-(3-bromopropoxy)-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Microwave-Assisted Synthesis of Novel Bis-Flavone Dimers as New Anticancer Agents

  摘要：

  在这项研究中，我们描述了一种基于微波的点击化学方法，用于制备一系列新型的双黄酮二聚体。取代的7-羟基和4'-羟基黄酮通过三唑环连接在一起。这些化合物易于合成，并且收率高。双黄酮在包括HCT116、HepG2、MCF7和MOLT-4在内的不同细胞系上进行了测试。几种类似物显示出抗癌活性，IC50值在20-60μM范围内。黄酮以其抗癌特性而闻名，这种方法为新的药用结构奠定了基础。

  DOI：

  10.2174/1570178615666180621094529

文献信息

• 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。
• 신규 화합물 및 이를 포함하는 염증성 질환과 암에 대한 진단 및 치료에 사용되는 MRI 조영제
  申请人：주식회사 테라노큐어

  公开号：KR20240040049A

  公开（公告）日：2024-03-27

  본 발명은 항염증, 항산화, 항암 효과가 있는 천연물 중 하나인 플라보노이드를 작용기로 가진 신규 화합물 및 이를 포함하는 MRI 조영제에 관한 것이다. 본 발명의 신규 화합물은 기존의 불용성 플라보노이드와는 다른 뛰어난 용해도를 토대로 정맥 투여가 가능하며, 소량으로도 항산화, 항염 및 항암 효과를 기대할 수 있고, 염증성 질환과 암을 표적하여 진단과 치료가 동시에 가능한 T 1 MRI 조영제로 활용될 수 있다.

  本发明涉及一种含有黄酮类化合物（作为抗炎、抗氧化和抗肿瘤活性成分的天然产物之一）的新型化合物及其作为MRI造影剂的应用。本发明的新型化合物与传统的难溶性黄酮类化合物不同，基于其优异的溶解性，使其可以通过静脉注射给药。并且，该化合物在少量使用时即可预期具有抗氧化、抗炎和抗肿瘤效果，并且可以通过靶向炎症性疾病和癌症，在T1加权MRI中实现诊断与治疗的双重功能。
• 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.
• 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