7-(4-溴丁氧基)-5-羟基-2-苯基-4H-色烯-4-酮 | 873302-27-3

• 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-(4-溴丁氧基)-5-羟基-2-苯基-4H-色烯-4-酮
• 英文名称: 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
• 英文别名: 7-(4-bromobutoxy)-5-hydroxy-2-phenylchromen-4-one
• CAS: 873302-27-3
• 化学式: C₁₉H₁₇BrO₄
• 分子量: 389.246
• InChiKey: WFRWFGLUNFBXNL-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  575.1±50.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(4-溴丁氧基)-5-羟基-2-苯基-4H-色烯-4-酮 在 silver nitrate 作用下， 以 乙腈 为溶剂， 以93%的产率得到4-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)硝酸丁酯
  参考文献：
  名称：

  Synthesis, characterization and vasculoprotective effects of nitric oxide-donating derivatives of chrysin

  摘要：

  Vascular complications are major causes of disability and death in patients with diabetes mellitus. It is often characterized by endothelial dysfunction. Studies have shown that either the loss of nitric oxide bioactivity or the decreased biosynthesis of NO is a central mechanism in endothelial dysfunction. As such, the delivery of exogenous NO is an attractive therapeutic option that has been used to slow the progress of diabetic vascular complications. In this paper, a novel group of hybrid nitric oxide-releasing chrysin derivatives was synthesized. The results indicated that all these chrysin derivatives exhibited in vitro inhibitory activities against aldose reductase and advanced glycation end-products formation. And some of them were even found to increase the glucose consumption of HepG2 cells. Furthermore, all compounds released NO upon incubation with phosphate buffer at pH 7.4. These hybrid ester NO donor pro-drugs offer a potential drug design concept for the development of therapeutic or preventive agents for vascular complications due to diabetes. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.056
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 7-(4-溴丁氧基)-5-羟基-2-苯基-4H-色烯-4-酮
  参考文献：
  名称：

  Design, synthesis, molecular docking, molecular dynamic simulation, and MMGBSA analysis of 7-O-substituted 5-hydroxy flavone derivatives

  摘要：

  DOI：

  10.1080/07391102.2023.2243520

文献信息

• Chrysin-piperazine conjugates as antioxidant and anticancer agents
  作者：Rahul V. Patel、Bhupendra Mistry、Riyaz Syed、Anuj K. Rathi、Yoo-Jung Lee、Jung-Suk Sung、Han-Seung Shinf、Young-Soo Keum

  DOI：10.1016/j.ejps.2016.02.011

  日期：2016.6

  bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH· and ABTS·+, particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive

  用1,4-二溴丁烷合成7-（4-溴丁氧基）-5-羟基-2-苯基-4H-铬-4-酮中间体处理ry素促进了ry素与多种哌嗪基团的结合，这些via嗪基团通过反应而装备在二甘醇单甲醚溶剂中用双（2-氯乙基）胺盐酸盐制得相应的胺。除了使用SRB分析评估宫颈癌癌细胞系（HeLa和CaSki）和卵巢癌细胞系SK-OV-3的体外抗癌功效外，还通过DPPH和ABTS生物测定法对制成品的自由基清除潜力进行了体外分析。 。可接受的7a-w毒性使用Madin-Darby犬肾（MDCK）细胞系进行检查。另外，使用人骨髓来源的间充质干细胞（hBM-MSC）检查了所提供化合物的细胞毒性性质。总的来说，7a-w显示出清除DPPH ·和ABTS ·+的显着抗氧化能力，尤其是类似物7f，7j，7k，7l，7n，7q，7v，7w具有清除自由基的活性。已确定类似物7j和7o是针对HeLa和CaSki细胞系的高活性候选物，而7h和
• Sulfonylpiperazines based on a flavone as antioxidant and cytotoxic agents
  作者：Rahul V. Patel、Bhupendra M. Mistry、Riyaz Syed、Nikhil M. Parekh、Han‐Seung Shin

  DOI：10.1002/ardp.201900051

  日期：2019.9

  Chrysin‐based sulfonylpiperazines 7a‐k were synthesized and investigated for their in vitro free radical scavenging potential as well as cytotoxic efficacies against selected cancer cell lines. Cytotoxicity of the new compounds toward noncancer cells was confirmed using the SRB assay against Madin–Darby Canine Kidney cells. Reaction of piperazine with different substituted benzenesulfonyl chlorides

  合成了基于白杨素的磺酰基哌嗪 7a-k，并研究了它们的体外自由基清除能力以及对选定癌细胞系的细胞毒性作用。使用针对 Madin-Darby 犬肾细胞的 SRB 测定证实了新化合物对非癌细胞的细胞毒性。哌嗪与不同取代苯磺酰氯在三乙胺提供的磺酰哌嗪 (3a-k) 中反应，然后与 7-(4-溴丁氧基)-5-羟基-2-苯基-4H-色胺-4-酮 (6 ) 制备白杨素与 1,4-二溴丁烷反应得到最终衍生物 7a-k。结果表明，白杨素-磺酰基哌嗪比以前研究的白杨素-哌嗪前体具有更好的抗氧化和抗癌功效。例如，化合物 7h、7j 和 7k 与 4-OCF3、4-OCH3、和 2,4-diOCH3 基团对 2,2-diphenyl-1-picrylhydrazyl (DPPH) 和 2,2'-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) 自由基
• 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。