3-(benzyloxy)-2-bromo-4-methoxy-N-methylbenzamide | 1233979-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(benzyloxy)-2-bromo-4-methoxy-N-methylbenzamide
• 英文别名: 2-bromo-4-methoxy-N-methyl-3-phenylmethoxybenzamide
• CAS: 1233979-39-9
• 化学式: C₁₆H₁₆BrNO₃
• 分子量: 350.212
• InChiKey: LMYOITDCLVCFGA-UHFFFAOYSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  423.4±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(benzyloxy)-2-bromo-4-methoxy-N-methylbenzamide 在 铜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6,6'-bis(benzyloxy)-5,5'-dimethoxy-N,N'-dimethylbiphenyl-2,2'-dicarboxamide
  参考文献：
  名称：

  Synthesis of novel taspine diphenyl derivatives as fluorescence probes and inhibitors of breast cancer cell proliferation

  摘要：

  通过在Ta-dD的基本结构中引入不同的香豆素荧光基团，设计并合成了两种新型taspine联苯衍生物（Ta-dD）。这两种化合物的主要优点是它们可以同时用作荧光探针和抑制剂。在本研究中，测量了探针的荧光特性并测试了它们对四种乳腺癌细胞系的抑制作用。在正常条件下将不同浓度的荧光探针添加到MCF-7乳腺癌细胞中进行荧光成像分析。结果表明，这两种新化合物不仅具有荧光，而且能够抑制对不同乳腺癌细胞系的影响，这表明它们可能进一步用作示踪分析中的双功能荧光探针。版权所有 © 2011 约翰·威利父子有限公司

  DOI：

  10.1002/bio.1331
• 作为产物：
  描述：

  2-溴-3-羟基-4-甲氧基苯甲醛 在 sodium dihydrogenphosphate 、 氯化亚砜 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 11.17h， 生成 3-(benzyloxy)-2-bromo-4-methoxy-N-methylbenzamide
  参考文献：
  名称：

  Synthesis and Cytotoxic Evaluation of Novel Symmetrical Taspine Derivatives as Anticancer Agents

  摘要：

  有研究表明，塔斯平衍生物可作为抗癌剂，因此我们设计并合成了一类新型的对称联苯衍生物。我们评估了联苯类化合物对五种人类肿瘤和正常细胞系的细胞毒性和抗肿瘤活性。结果表明，大多数化合物的抗癌活性相当于或高于阳性对照。化合物 (11) 和 (12) 的细胞毒性活性最强，IC50 值介于 19.41 μM 和 29.27 μM 之间。这些化合物对 ECV304 人转化内皮细胞的强效抗增殖能力表明，这些联苯有可能成为抗血管生成剂。我们还根据实验结果回顾了结构与活性之间的关系。我们的研究结果为进一步开发对称联苯衍生物作为潜在的新型抗癌剂提供了一个良好的起点。

  DOI：

  10.2174/157340611796150914

文献信息

• Facile Synthesis and Biological Evaluation of Novel Symmetrical Biphenyls as Antitumor Agents
  作者：Jie Zhang、Yanmin Zhang、Xiaoyan Pan、Chen Wang、Zhigang Hu、Sicen Wang、Langchong He

  DOI：10.2174/157340612800493656

  日期：2012.4.26

  anticancer agents, eighteen symmetrical biphenyl derivatives structurally related to taspine were synthesized and evaluated in vitro and in vivo. All the compounds were prepared with varied substitutions in the phenyl ring of aniline moiety. The cytotoxicity and anticancer activity of biphenyls was evaluated against various human tumor and normal cell line. Antiproliferative assays indicated that some of them

  作为我们以前开发抗癌药工作的延续，我们合成了十八种与他山碱有关的对称联苯衍生物，并在体外和体内进行了评估。制备了在苯胺部分的苯环中具有不同取代基的所有化合物。联苯对各种人类肿瘤和正常细胞系的细胞毒性和抗癌活性进行了评估。抗增殖试验表明，其中一些表现出有效的抗癌活性。这些化合物对ECV304的强抗增殖活性表明，这些联苯可用作抗血管生成剂。高活性化合物（2）还在体内对癌细胞系表现出有效的生长抑制作用。
• Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents
  作者：Jie Zhang、Yanmin Zhang、Yuanyuan Shan、Na Li、Wei Ma、Langchong He

  DOI：10.1016/j.ejmech.2010.03.001

  日期：2010.7

  Antiangiogenic therapy might represent a new promising anticancer therapeutic strategy. Taspine can significantly inhibit cell proliferation of human umbilical vein endothelial cells (HUVECs) induced by vascular endothelial growth factor-165, which is crucial for angiogenesis. In this study, a series of novel taspine derivatives were synthesized and screened for in vitro anticancer and antiangiogenesis activities. The majority of the derivatives demonstrated a moderate degree of cytotoxicity against human cancer cell lines. One of them (14) exhibited much better antiproliferative activity against CACO-2 (IC(50) = 52.5 mu M) and ECV304 (IC(50) = 2.67 mu M) cells than taspine did. Some of them were also effective in antiproliferative assays against HUVECs. The in silico estimate of solubility of title compounds were higher than that of taspine. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and Cytotoxic Evaluation of Novel Symmetrical Taspine Derivatives as Anticancer Agents
  作者：Jie Zhang、Yanmin Zhang、Xiaoyan Pan、Sicen Wang、Langchong He

  DOI：10.2174/157340611796150914

  日期：2011.7.1

  It has been demonstrated that taspine derivatives act as anticancer agents, thus we designed and synthesized a novel class of symmetrical biphenyl derivatives. We evaluated the cytotoxicity and antitumor activity of biphenyls against five human tumor and normal cell lines. The results indicated that the majority of the compounds exhibited anticancer activity equivalent to or greater than the positive control. Compounds (11) and (12) demonstrated the most potent cytotoxic activity with IC50 values between 19.41 μM and 29.27 μM. The potent antiproliferative capabilities of these compounds against ECV304 human transformed endothelial cells indicated that these biphenyls could potentially serve as antiangiogenic agents. We also reviewed the relationship between structure and activity based on the experimental results. Our findings provide a good starting point for further development of symmetrical biphenyl derivatives as potential novel anticancer agents.

  有研究表明，塔斯平衍生物可作为抗癌剂，因此我们设计并合成了一类新型的对称联苯衍生物。我们评估了联苯类化合物对五种人类肿瘤和正常细胞系的细胞毒性和抗肿瘤活性。结果表明，大多数化合物的抗癌活性相当于或高于阳性对照。化合物 (11) 和 (12) 的细胞毒性活性最强，IC50 值介于 19.41 μM 和 29.27 μM 之间。这些化合物对 ECV304 人转化内皮细胞的强效抗增殖能力表明，这些联苯有可能成为抗血管生成剂。我们还根据实验结果回顾了结构与活性之间的关系。我们的研究结果为进一步开发对称联苯衍生物作为潜在的新型抗癌剂提供了一个良好的起点。
• Synthesis of novel taspine diphenyl derivatives as fluorescence probes and inhibitors of breast cancer cell proliferation
  作者：Huaizhen He、Yingzhuan Zhan、Yanmin Zhang、Jie Zhang、Langchong He

  DOI：10.1002/bio.1331

  日期：2012.7

  Two novel taspine diphenyl derivatives (Ta-dD) were designed and synthesized by introducing different coumarin fluorescent groups into the basic structure of Ta-dD. The main advantage of these two compounds is that they can be used as fluorescence probes and inhibitors simultaneously. In the present study, the fluorescent properties of the probes were measured and their inhibition of four breast cancer cell lines was tested. Different concentrations of the fluorescence probe were added to MCF-7 breast cancer cells for fluorescence imaging analysis under normal conditions. The results suggested that both of the new compounds have not only fluorescence but also the ability to inhibit effects on different breast cancer cell lines, which indicates their possible further use as dual functional fluorescence probes in tracer analysis. Copyright © 2011 John Wiley & Sons, Ltd.

  通过在Ta-dD的基本结构中引入不同的香豆素荧光基团，设计并合成了两种新型taspine联苯衍生物（Ta-dD）。这两种化合物的主要优点是它们可以同时用作荧光探针和抑制剂。在本研究中，测量了探针的荧光特性并测试了它们对四种乳腺癌细胞系的抑制作用。在正常条件下将不同浓度的荧光探针添加到MCF-7乳腺癌细胞中进行荧光成像分析。结果表明，这两种新化合物不仅具有荧光，而且能够抑制对不同乳腺癌细胞系的影响，这表明它们可能进一步用作示踪分析中的双功能荧光探针。版权所有 © 2011 约翰·威利父子有限公司