(E)-3-(2,3-dihydrobenzo[b][1,4]dioxane-6-yl)-1-phenylprop-2-en-1-one | 5533-90-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(2,3-dihydrobenzo[b][1,4]dioxane-6-yl)-1-phenylprop-2-en-1-one
• 英文别名: 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-phenylprop-2-en-1-one
• CAS: 5533-90-4
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: JMBNMSBPJPYQPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  (E)-3-(2,3-dihydrobenzo[b][1,4]dioxane-6-yl)-1-phenylprop-2-en-1-one 在 镍 氢气 作用下， 以 1,4-二氧六环 为溶剂， 以96%的产率得到6-(3-Hydroxy-3-phenylpropyl)benzo-1,4-dioxane
  参考文献：
  名称：

  Synthesis and local-anesthetic activity of 6-[ω-amino-ω)-arylalkyl]benzo-1,4-dio anes

  摘要：

  DOI：

  10.1007/bf00769801
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (E)-3-(2,3-dihydrobenzo[b][1,4]dioxane-6-yl)-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  4,5-Dihydropyrazole derivatives containing oxygen-bearing heterocycles as potential telomerase inhibitors with anticancer activity

  摘要：

  端粒和端粒酶与某些癌症的发生发展密切相关。在鉴定出端粒酶关键活性部位后，基于以往的研究，为了增强二氢吡唑衍生物抑制端粒酶的能力，我们设计了一系列含有杂环氧基的新型4,5-二氢吡唑衍生物。端粒酶抑制实验表明，化合物10a显示出最强的抑制活性，其对端粒酶的IC50值为0.6 μM。细胞增殖实验表明，10a对胃癌细胞SGC-7901具有很高的活性，其IC50值为10.95 ± 0.60 μM。流式细胞分析和western blot结果显示，10a可诱导细胞凋亡和自噬。对接模拟显示，10a可与端粒酶的活性位点很好地结合，并作为端粒酶抑制剂发挥作用。同时，为了能更好地指导设计出新的具有更强端粒酶抑制活性的化合物，我们构建了三维定量构效关系(3D-QSAR)模型。

  DOI：

  10.1039/c4ra02200a

文献信息

• Dihydropyrazole Derivatives Containing Benzo Oxygen Heterocycle and Sulfonamide Moieties Selectively and Potently Inhibit COX-2: Design, Synthesis, and Anti-Colon Cancer Activity Evaluation
  作者：Xiao-Qiang Yan、Zhong-Chang Wang、Bo Zhang、Peng-Fei Qi、Gui-Gen Li、Hai-Liang Zhu

  DOI：10.3390/molecules24091685

  日期：——

  Cyclooxygenase-2 (COX-2) as a rate-limiting metabolism enzyme of arachidonic acid has been found to be implicated in tumor occurrence, angiogenesis, metastasis as well as apoptosis inhibition, regarded as an attractive therapeutic target for cancer therapy. In our research, a series of dihydropyrazole derivatives containing benzo oxygen heterocycle and sulfonamide moieties were designed as highly potent

  已发现环氧合酶-2 (COX-2) 作为花生四烯酸的限速代谢酶与肿瘤发生、血管生成、转移以及细胞凋亡抑制有关，被认为是癌症治疗的有吸引力的治疗靶点。在我们的研究中，通过对已知 COX-2 抑制剂的计算机辅助药物分析，将一系列含有苯并氧杂环和磺酰胺部分的二氢吡唑衍生物设计为高效且选择性的 COX-2 抑制剂。共合成了26种化合物，多角度评价了体外和体内COX-2抑制作用和药理效率。其中，化合物4b对SW620细胞表现出最优异的抗增殖活性，IC50比塞来昔布（IC50 = 1.29±0.04 µM）为0.86±0.02 µM。
• 一类新型三芳基吡唑啉衍生物的制备方法及其在抗癌药物中的应用
  申请人：南京大学

  公开号：CN110467605B

  公开（公告）日：2022-07-29

  本发明公开了一类新型三芳基吡唑啉衍生物制备方法及应用。本发明属于药物化学领域。本发明的化合物都显示了强效的BRAFV600E抑制活性，在减弱BRAFWT抑制效应方面有可喜的变化，因此本发明的一类新型三芳基吡唑啉衍生物可以应用于制备抗癌药物。
• Synthesis, biological evaluation, 3D-QSAR studies of novel aryl-2H-pyrazole derivatives as telomerase inhibitors
  作者：Yin Luo、Shuai Zhang、Ke-Ming Qiu、Zhi-Jun Liu、Yu-Shun Yang、Jie Fu、Wei-Qing Zhong、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2012.12.010

  日期：2013.2

  A series of novel aryl-2H-pyrazole derivatives bearing 1,4-benzodioxan or 1,3-benzodioxole moiety were designed as potential telomerase inhibitors to enhance the ability of aryl-2H-pyrazole derivatives to inhibit telomerase, a target of anticancer. The telomerase inhibition tests showed that compound 16A displayed the most potent inhibitory activity with IC50 value of 0.9 mu M for telomerase. The antiproliferative tests showed that compound 16A exhibited high activity against human gastric cancer cell SGC-7901 and human melanoma cell B16-F10 with IC50 values of 18.07 and 5.34 mu M, respectively. Docking simulation showed that compound 16A could bind well with the telomerase active site and act as telomerase inhibitor. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent telomerase inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and antihepatotoxic activity of 5-(2,3-dihydro-1,4-benzodioxane-6-yl)-3-substituted-phenyl-4,5-dihydro-1H-pyrazole derivatives
  作者：Habibullah Khalilullah、Shamshir Khan、Mohamed Jawed Ahsan、Bahar Ahmed

  DOI：10.1016/j.bmcl.2011.10.056

  日期：2011.12

  In continuance of our search for newer antihepatotoxic agents some novel pyrazoline derivatives containing 1,4-dioxane ring system were synthesized starting from 3-(2,3-dihydro-1,4-benzodioxane-6-yl)-1-substituted-phenylprop-2-en-1-one. Some of the synthesized compounds were evaluated for antihepatotoxic activity against CCl4-induced hepatotoxicity in rats. Among them some compounds have shown significant antihepatotoxic activity comparable to standard drug silymarin. (C) 2011 Elsevier Ltd. All rights reserved.
• 4,5-Dihydropyrazole derivatives containing oxygen-bearing heterocycles as potential telomerase inhibitors with anticancer activity
  作者：Yin Luo、Yang Zhou、Jie Fu、Hai-Liang Zhu

  DOI：10.1039/c4ra02200a

  日期：——

  Telomere and telomerase were closely related to the occurrence and development of some cancers. After the key active site of telomerase was identified, to enhance the ability of dihydropyrazole derivatives to inhibit telomerase, we designed a series of novel 4,5-dihydropyrazole derivatives containing heterocyclic oxygen moiety based on previous studies. The telomerase inhibition assay showed that compound 10a displayed the most potent inhibitory activity with an IC50 value of 0.6 μM for telomerase. The antiproliferative assay showed that 10a exhibited high activity against human gastric cancer cell SGC-7901 with an IC50 value of 10.95 ± 0.60 μM. Flow cytometric analysis and western blot results showed that 10a induced both apoptosis and autophagy. A docking simulation showed that 10a could bind well to the active site of telomerase and act as a telomerase inhibitor. The 3D-QSAR model was also built to provide a more pharmacological understanding that could be used to design new agents with more potent telomerase inhibitory activity.

  端粒和端粒酶与某些癌症的发生发展密切相关。在鉴定出端粒酶关键活性部位后，基于以往的研究，为了增强二氢吡唑衍生物抑制端粒酶的能力，我们设计了一系列含有杂环氧基的新型4,5-二氢吡唑衍生物。端粒酶抑制实验表明，化合物10a显示出最强的抑制活性，其对端粒酶的IC50值为0.6 μM。细胞增殖实验表明，10a对胃癌细胞SGC-7901具有很高的活性，其IC50值为10.95 ± 0.60 μM。流式细胞分析和western blot结果显示，10a可诱导细胞凋亡和自噬。对接模拟显示，10a可与端粒酶的活性位点很好地结合，并作为端粒酶抑制剂发挥作用。同时，为了能更好地指导设计出新的具有更强端粒酶抑制活性的化合物，我们构建了三维定量构效关系(3D-QSAR)模型。