7-(2-溴乙氧基)-5-羟基-2-苯基-4H-色烯-4-酮 | 41988-26-5

• 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-(2-溴乙氧基)-5-羟基-2-苯基-4H-色烯-4-酮
• 英文名称: 7-(2-bromoethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one
• 英文别名: 7-(2-bromoethoxy)-5-hydroxy-2-phenylchromen-4-one
• CAS: 41988-26-5
• 化学式: C₁₇H₁₃BrO₄
• 分子量: 361.192
• InChiKey: HCKJBEDMNKXMTF-UHFFFAOYSA-N

物化性质

• 熔点：
  157-158 °C
• 沸点：
  549.5±50.0 °C(Predicted)
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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-(2-溴乙氧基)-5-羟基-2-苯基-4H-色烯-4-酮 在 silver nitrate 作用下， 以 乙腈 为溶剂， 生成 2-(5-羟基-4-氧代-2-苯基-4H-色烯-7-基氧基)硝酸乙酯
  参考文献：
  名称：

  Synthesis and promotion angiogenesis effect of chrysin derivatives coupled to NO donors

  摘要：

  Two types of new chrysin derivatives were prepared by coupling NO donors of alkyl nitrate and furazan derivatives and were fully characterized by H-1 NMR and other techniques. These compounds were tested in human umbilical vein endothelial cells (HUVECs-12) and all the compounds exhibited cell proliferation. Notable effects of promoting angiogenesis were observed for all the modified compounds using chick chorioallantoic membrane (CAM) assay. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.116
• 作为产物：
  描述：

  2-羟基-4,6-二甲氧基苯乙酮 在 吡啶 、 硫酸 、 吡啶盐酸盐 、 potassium carbonate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 丙酮 为溶剂， 反应 34.25h， 生成 7-(2-溴乙氧基)-5-羟基-2-苯基-4H-色烯-4-酮
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel chrysin derivatives

  摘要：

  A series of chrysin derivatives 8a-8v were prepared and tested in vitro against HCT-116 (human colon cancer cell line), Hela (human cervical carcinoma cell line), DU-145 (human prostate cell line), K562 (human leukemia cell line), and SGC-7901 (human gastric cancer cell line). The chemical structures of these compounds were confirmed by means of MS, IR, H-1 NMR, C-13 NMR, and elemental analysis. Among these derivatives, 7-(2-(piperazin-1-yl)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, 8n, had the strongest activity against HCT-116, Hela, DU-145, K562, and SGC-7901 cells.

  DOI：

  10.1007/s00044-010-9395-1

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, characterization and antioxidant activity of organoselenium and organotellurium compound derivatives of chrysin
  作者：Sergio F. Fonseca、David B. Lima、Diego Alves、Raquel G. Jacob、Gelson Perin、Eder João Lenardão、Lucielli Savegnago

  DOI：10.1039/c4nj02329c

  日期：——

  evaluation of the antioxidant activity of several organochalcogen-containing chrysin derivatives (Se and Te). The semi-synthetic compounds were easily synthesized in good to excellent yields by the reaction of 7-(2-bromoethoxy)-chrysin with nucleophilic organoselenium and organotellurium species. The antioxidant properties of Se- and Te-containing chrysin derivatives were evaluated by three different in vitro

  在这里，我们描述了几种有机硫属元素的绿素衍生物（Se和Te）的合成和抗氧化活性的评估结果。通过7-（2-溴乙氧基）-胰蛋白酶与亲核性有机硒和有机碲物种的反应，可以容易地以良好至极好的产率合成半合成化合物。通过三种不同的体外测定法评估了含Se和Te的菊花衍生物的抗氧化性能，即1,1-二苯基-2-吡啶-2-肼基（DPPH）和2,2'-叠氮基双（3-乙基苯并噻唑啉） 6-磺酸）（ABTS）自由基清除活性和铁离子还原抗氧化能力（FRAP）。化合物4i（包含丁基碲部分）和4j（含有4-苯基碲部分）（比4-丁烯菊和硒类似物）具有更高的活性，其中化合物4i是最有效的抗氧化剂。
• 含氮芥基黄酮类衍生物、其制备方法及抗肿瘤 方向应用
  申请人：北京师范大学

  公开号：CN109384760B

  公开（公告）日：2020-07-28

  本发明公开了一类含氮芥基黄酮类衍生物的制备方法及它们在抗肿瘤活性研究中的用途。如式Ⅰ和式Ⅱ所示，其中n为1,2,3。目标化合物均未见文献报道。此类化合物可抑制多种肿瘤细胞的生长活性。实验表明，目标化合物对测试的7种癌细胞都显示出了较好的抗肿瘤活性，与现有的抗肿瘤药物5‑氟尿嘧啶相比，本发明的目标化合物对多种肿瘤细胞的生长抑制活性，都明显高于它；其中目标化合物Ⅱ2抗肿瘤效果最好，对于Hela、DU145、PC‑3、MCF‑7、SH‑SY5Y细胞而言，它们的IC50值均在10μM以下，与抗肿瘤药物顺铂相比，都在同一个数量级。进一步研究发现，目标化合物Ⅱ2可通过将HeLa细胞周期阻滞在G2/M期诱导细胞凋亡，目标化合物Ⅱ2有望成为新型的抗肿瘤药物。
• 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。