7-(3-溴丙氧基)-5-羟基-2-苯基色烯-4-酮 | 873302-14-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 7-(3-溴丙氧基)-5-羟基-2-苯基色烯-4-酮
• 英文名称: 7-(3-bromopropoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
• 英文别名: 7-(3-Bromopropoxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one；7-(3-bromopropoxy)-5-hydroxy-2-phenylchromen-4-one
• CAS: 873302-14-8
• 化学式: C₁₈H₁₅BrO₄
• 分子量: 375.219
• InChiKey: IGBVXHRVPIKEIW-UHFFFAOYSA-N

物化性质

• 沸点：
  565.2±50.0 °C(Predicted)
• 密度：
  1.513±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(3-溴丙氧基)-5-羟基-2-苯基色烯-4-酮 在 氯化亚砜 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 96.0h， 生成 7-[3-[bis(2-chloroethyl)amino]propoxy]-5-hydroxy-2-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  类黄酮氮芥子衍生物的合成及其体外抗肿瘤活性的研究。

  摘要：

  合成了几种新颖的类黄酮氮芥子衍生物，并通过体外MTT分析评估了其对七种人类癌细胞系（HeLa，A549，HepG2，MCF7，SH-SY5Y，PC-3，DU145）的抗增殖活性。所得的IC 50显示大多数化合物对七种细胞系表现出更好的抑制活性。一些化合物的IC50值低于众所周知的美法仑。特别是，化合物8b是抑制HeLa细胞的最有前途的化合物，IC50值为1.43μM。它对这七个细胞系显示出极好的抗肿瘤活性。此外，它可以阻止HeLa在G2 / M期的细胞周期并诱导细胞凋亡。线粒体膜电位的丧失可能是细胞凋亡的介导因子。

  DOI：

  10.1016/j.bioorg.2020.103613
• 作为产物：
  描述：

  苯甲酰氯 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 12.42h， 生成 7-(3-溴丙氧基)-5-羟基-2-苯基色烯-4-酮
  参考文献：
  名称：

  Multifunctional tacrine–flavonoid hybrids with cholinergic, β-amyloid-reducing, and metal chelating properties for the treatment of Alzheimer's disease

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.09.024

文献信息

• Design, synthesis and biological evaluation of chrysin benzimidazole derivatives as potential anticancer agents
  作者：Zhe Wang、Xiangping Deng、Shujuan Xiong、Runde Xiong、Juan Liu、Liu Zou、Xiaoyong Lei、Xuan Cao、Zhizhong Xie、Yanming Chen、Yunmei Liu、Xing Zheng、Guotao Tang

  DOI：10.1080/14786419.2017.1389940

  日期：2018.12.17

  A series of chrysin benzimidazole derivatives were synthesised and evaluated for their anticancer activity in the search for potential anticancer agents. Among them, compound 18 displayed the most potent anti-proliferative activity against MFC cells with IC50 values of 25.72 ± 3.95 μM. The flow cytometry results displayed that compound 18 induced apoptosis of MFC cells in a dose-dependent manner and

  合成了一系列的Chrysin苯并咪唑衍生物，并在寻找潜在的抗癌剂中评估了它们的抗癌活性。其中，化合物18对MFC细胞表现出最有效的抗增殖活性，IC 50值为25.72±3.95μM。流式细胞术结果显示化合物18以剂量依赖性方式诱导MFC细胞凋亡，并使细胞周期停滞在G0 / G1期。此外，还对荷瘤小鼠体内的初步抗癌活性进行了研究，化合物18对肿瘤的生长具有良好的抑制作用。这些结果表明化合物18 具有良好的抗癌活性，经过进一步优化和评估，有望成为潜在的抗癌剂。
• Synthesis and evaluation of antitumour activity <i>in vitro</i> and <i>in vivo</i> of chrysin salicylate derivatives
  作者：Xiangping Deng、Zihao Zhao、Shujuan Xiong、Runde Xiong、Juan Liu、Zhe Wang、Liu Zou、Xiaoyong Lei、Xuan Cao、Zhizhong Xie、Yanming Chen、Xing Zheng、Yunmei Liu、Guotao Tang

  DOI：10.1080/14786419.2017.1371159

  日期：2018.9.17

  A series of chrysin salicylate derivatives as potential antitumour agents were synthesised and evaluated their antitumour activities in vitro and in vivo. Most of the compounds exhibited moderate to good activities against MCF-7 cells, HepG2 cells, MGC-803cells and MFC cells. Among them, compound 3f showed the most potent activity against MGC-803 cells and MFC cells with IC50 values of 23.83 ± 3.68

  一系列白杨素水杨酸酯衍生物作为潜在的抗肿瘤剂的合成和评价了它们的抗肿瘤活性在体外和体内。大多数化合物对MCF-7细胞，HepG2细胞，MGC-803细胞和MFC细胞表现出中等至良好的活性。其中，化合物3f对MGC-803细胞和MFC细胞表现出最强的活性，IC 50值分别为23.83±3.68和27.34±5.21μM。流式细胞仪分析再次确认，化合物3F促进肿瘤细胞G1 /化合物的抑制作用下S嵌段的发生3F。化合物3f 与阳性对照5-Fu和空白对照盐水相比，荷瘤小鼠具有更高的抗肿瘤功效。
• Synthesis of Some New Chrysin Derivatives and Their Biological Assessment as Antibacterial, Antibiofilm and Antifungal Agent
  作者：S. Bhowmik、T. Das、S. Ghosh、B.K. Sharma、S. Majumdar、U.C. De

  DOI：10.14233/ajchem.2018.21167

  日期：——

  Some new derivatives of natural chrysin have been synthesized and evaluated for antibacterial, antibiofilm and antifungal activities. Three compounds, namely 2a, 2e, 2i showed excellent activities (MIC 14.0-18.3 μg/mL) against six bacterial and two fungal type strains while most of the other compounds showed comparatively low to moderate values of such activities. Significant antibiofilm and bactericidal activities (MBC ranges from 17-20 μg/mL) were also observed for 2a, 2e, 2i against pneumonia causing two bacterial strains. This study further indicated that the chrysin compounds with 7-O-alkyl type substitution were much more effective than corresponding aryl substituted congeners which signifies that 7-O position of chrysin is crucial for antimicrobial activities. Thus, this article would contribute to further design and development of potential antimicrobial agents via structural modulation of natural chrysin, which is a potential molecular skeleton with diverse biological activities.

  一些新的天然黄酮衍生物已经合成并评估了其抗菌、抗生物膜和抗真菌活性。三种化合物，即2a、2e和2i在六种细菌和两种真菌类型菌株中显示出优异的活性（MIC 14.0-18.3 μg/mL），而大多数其他化合物的活性则相对较低到中等。对于导致肺炎的两种细菌菌株，2a、2e和2i也显示出显著的抗生物膜和杀菌活性（MBC范围为17-20 μg/mL）。本研究进一步表明，具有7-O-烷基取代的黄酮化合物比相应的芳基取代同类物更为有效，这表明黄酮的7-O位点对抗微生物活性至关重要。因此，本文将有助于通过对天然黄酮的结构调制，进一步设计和开发潜在的抗微生物剂，而天然黄酮是一种具有多种生物活性的潜在分子骨架。
• Novel photosensitizing properties of porphyrin–chrysin derivatives with antitumor activity in vitro
  作者：Ding Liu、Qizhi Zhang、Lang Zhang、Wenmei Yu、Huizhi Long、Jun He、Yunmei Liu

  DOI：10.1177/1747519820907248

  日期：2020.7

  Photodynamic therapy is a promising cancer treatment with the advantages of low toxicity, high efficiency, and noninvasiveness. In this study, 23 novel porphyrin–chrysin derivatives are synthesized using alkyl carbon chains as bridges. We use human gastric cancer cells (MGC-803) and human cervical cancer cells to evaluate the in vitro antitumor activity of all the porphyrin–chrysin derivatives, with

  光动力疗法具有低毒、高效、无创等优点，是一种很有前景的癌症治疗方法。在这项研究中，使用烷基碳链作为桥接合成了 23 种新型卟啉-白杨素衍生物。我们使用人胃癌细胞 (MGC-803) 和人宫颈癌细胞来评估所有卟啉 - 白杨素衍生物的体外抗肿瘤活性，以 5-氟尿嘧啶 (5-Fu) 作为阳性对照。制备的几种化合物表现出有效的光动力杀伤作用，其中5-羟基-2-苯基-7-(2-(4-(10,15,20-三(4-羟基苯基)卟啉-5-基)苯氧基) ethoxy)-4H-chromen-4-one 对人宫颈癌细胞的抗增殖活性最高，半数抑制浓度为 26.51 ± 1.15 µM。
• Synthesis, structural study and biological activity of new derivatives of chrysin containing a 2-mercaptopyridyl or 5-(trifluoromethyl)-2-mercaptopyridyl fragments
  作者：Alejandro Valdez-Calderón、Simplicio González-Montiel、Diego Martínez-Otero、Ataulfo Martínez-Torres、José Manuel Vásquez-Pérez、Carlos Molina-Vera、J. Martín Torres-Valencia、José G. Alvarado-Rodríguez、Julian Cruz-Borbolla

  DOI：10.1016/j.molstruc.2016.01.055

  日期：2016.4

  Abstract New derivatives of chrysin containing 2-mercaptopyridine (2a–2e) or 5-(trifluoromethyl)-2-mercaptopyridine (3a–3e) moieties were prepared from the reaction between bromides (1a–1e) and 2-mercaptopyridine or 5-(trifluoromethyl)-2-mercaptopyridine, respectively. Their structures were elucidated by NMR, IR and elemental analysis. The molecular structure of compounds 1a, 1c–1e, 2b–2e and 3a was

  摘要 含有 2-巯基吡啶 (2a-2e) 或 5-(三氟甲基)-2-巯基吡啶 (3a-3e) 部分的白杨素的新衍生物是通过溴化物 (1a-1e) 和 2-巯基吡啶或 5-(三氟甲基）-2-巯基吡啶，分别。通过NMR、IR和元素分析阐明了它们的结构。通过单晶 X 射线衍射研究确定了化合物 1a、1c-1e、2b-2e 和 3a 的分子结构。这些结构中的所有环几乎共面，它们在酚羟基 H 原子和羰基 O 原子之间显示出分子内氢键，形成六元环。晶体堆积还显示出各种各样的分子间接触，例如 C–H⋯A、π–π、C–H⋯π 和孤对相互作用⋯π 相互作用，这些相互作用得到了分子中原子量子理论 (QTAIM) 的支持，Hirshfeld 曲面和指纹图分析。在线虫秀丽隐杆线虫的生长试验中测试了所有化合物的生物活性。化合物2e、3b和3c抑制幼虫发育。