5-iodo-1-(4-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole | 1207328-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-iodo-1-(4-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 5-iodo-1-[(4-methoxyphenyl)methyl]-4-phenyltriazole
• CAS: 1207328-55-9
• 化学式: C₁₆H₁₄IN₃O
• 分子量: 391.211
• InChiKey: UADHIDVIMPKTLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.94
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-iodo-1-(4-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole 在 bis-triphenylphosphine-palladium(II) chloride 、 三氯化硼 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 11.0h， 生成 4,5-diphenyl-1-(4-(3-(pyrrolidin-1-yl)propoxy)benzyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Design, synthesis and comparative analysis of triphenyl-1,2,3-triazoles as anti-proliferative agents

  摘要：

  Herein, a series of triaryl-1,2,3-triazoles, in order to check cytotoxicity on breast cancer cell lines have been synthesized with pendent benzyl ring to mimic the phenolic A ring of Tamoxifene. The biological results indicated that most of the compounds possessed comparative anti-proliferative activities in both ER + ve (MCF-7) and ER-ve (MDA-MB-231) breast cancer cell lines. Among synthesized derivatives, five compounds 8f, 8i, 8j, 8n and 8p showed anti-proliferative activities at <5 μM against MCF-7 cell line and three compounds 8e, 8f and 8j show IC₅₀ value greater than 30 μM in FR-2 cells (normal cell). Moreover, to understand the mechanistic behavior of the selective compound 8f, various studies performed viz. surface morphological changes by bright field microscopic examination, nuclear morphological alteration by DAPI staining, measurement of intracellular ROS level and determination of change in mitochondrial membrane potential. It was observed that, the selective compound 8f associated with higher ROS generation along with decrease in mitochondrial membrane potential in addition to surface and nuclear morphological alterations such as reduction in number and shrinkage of cells coupled with nuclear blabbing indicating sign of apoptosis. Further, molecular docking study in comparison to tamoxifen was also carried out to investigate the interaction of 8f with ER-α which favors its possible mode of anticancer action.

  DOI：

  10.1016/j.ejmech.2020.112813
• 作为产物：
  描述：

  苯乙炔 在 copper(l) iodide 、 sodium azide 、 碘 、 三乙胺 、 β-环糊精 作用下， 以 水 为溶剂， 反应 4.5h， 生成 5-iodo-1-(4-methoxybenzyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Design, synthesis and comparative analysis of triphenyl-1,2,3-triazoles as anti-proliferative agents

  摘要：

  Herein, a series of triaryl-1,2,3-triazoles, in order to check cytotoxicity on breast cancer cell lines have been synthesized with pendent benzyl ring to mimic the phenolic A ring of Tamoxifene. The biological results indicated that most of the compounds possessed comparative anti-proliferative activities in both ER + ve (MCF-7) and ER-ve (MDA-MB-231) breast cancer cell lines. Among synthesized derivatives, five compounds 8f, 8i, 8j, 8n and 8p showed anti-proliferative activities at <5 μM against MCF-7 cell line and three compounds 8e, 8f and 8j show IC₅₀ value greater than 30 μM in FR-2 cells (normal cell). Moreover, to understand the mechanistic behavior of the selective compound 8f, various studies performed viz. surface morphological changes by bright field microscopic examination, nuclear morphological alteration by DAPI staining, measurement of intracellular ROS level and determination of change in mitochondrial membrane potential. It was observed that, the selective compound 8f associated with higher ROS generation along with decrease in mitochondrial membrane potential in addition to surface and nuclear morphological alterations such as reduction in number and shrinkage of cells coupled with nuclear blabbing indicating sign of apoptosis. Further, molecular docking study in comparison to tamoxifen was also carried out to investigate the interaction of 8f with ER-α which favors its possible mode of anticancer action.

  DOI：

  10.1016/j.ejmech.2020.112813

文献信息

• β-CD/CuI catalyzed regioselective synthesis of iodo substituted 1,2,3-triazoles, imidazo[1,2-a]-pyridines and benzoimidazo[2,1-b]thiazoles in water and their functionalization
  作者：Divya Dheer、Ravindra K. Rawal、Virender Singh、P.L. Sangwan、Parthasarathi Das、Ravi Shankar

  DOI：10.1016/j.tet.2017.05.081

  日期：2017.7

  An environment benign process has been developed for the regioselective synthesis of 5-iodo-1,4-disubstituted-1,2,3-triazoles catalyzed by CuI/β-CD in water. Moreover, the process was manifested for the efficient synthesis of 2-iodo-imidazo[1,2-a]pyridines and 2-iodo-benzoimidazo[2,1-b]thiazoles in aqueous medium. Additionally, the iodinated derivatives were successfully modified via palladium catalyzed

  已经开发出一种环境友好的方法，用于在水中CuI /β-CD催化的5-碘-1,4-二取代-1,2,3-三唑的区域选择性合成。而且，在水性介质中有效合成2-碘-咪唑并[1,2- a ]吡啶和2-碘-苯并咪唑并[ 2,1- b ]噻唑的方法被证明。另外，通过钯催化的偶联反应成功地修饰了碘化衍生物。该方法的显着特征是在温和的反应条件下原位形成1-碘炔烃和烷基/芳基叠氮化物，高区域选择性以及使用水作为绿色溶剂。
• Efficient Synthesis of Diverse 5-Thio- or 5-Selenotriazoles: One-Pot Multicomponent Reaction from Elemental Sulfur or Selenium
  作者：Lin-Lin Zhang、Ya-Ting Li、Ting Gao、Sha-Sha Guo、Bei Yang、Zi-Hui Meng、Qi-Pu Dai、Zhi-Bin Xu、Qin-Pei Wu

  DOI：10.1055/s-0039-1690618

  日期：2019.11

  easy operation, and ligand-free CuI. A sequential multistep reaction toward 5-thio- or 5-selenotriazoles has been established by generation of both copper(I) triazolides and sulfenylating or selenylating agents in situ, starting from elemental sulfur or selenium. This reaction features mild conditions, readily available and broad-scope substrates, good functional group compatibility, high efficiency and

  抽象的 通过从元素硫或硒开始就地生成三唑啉铜（I）和亚磺酰化或硒化剂，已经建立了针对5-硫代三唑或5-硒代三唑的顺序多步反应。该反应具有温和的条件，易于获得的广谱底物，良好的官能团相容性，高效和区域选择性，易于操作和不含配体的CuI的特点。 通过从元素硫或硒开始就地生成三唑啉铜（I）和亚磺酰化或硒化剂，已经建立了针对5-硫代三唑或5-硒代三唑的顺序多步反应。该反应具有温和的条件，易于获得的广谱底物，良好的官能团相容性，高效和区域选择性，易于操作和不含配体的CuI的特点。
• Catalytic and Computational Studies of N-Heterocyclic Carbene or Phosphine-Containing Copper(I) Complexes for the Synthesis of 5-Iodo-1,2,3-Triazoles
  作者：Steven Lal、Henry S. Rzepa、Silvia Díez-González

  DOI：10.1021/cs500326e

  日期：2014.7.3

  Two complementary catalytic systems are reported for the 1,3-dipolar cycloaddition of azides and iodoalkynes. These are based on two commercially available/readily available copper complexes, [CuCl(IPr)] or [CuI(PPh3)3], which are active at low metal loadings (PPh3 system) or in the absence of any other additive (IPr system). These systems were used for the first reported mechanistic studies on this

  据报道，对于叠氮化物和碘代炔烃的1，3-偶极环加成反应，存在两个互补的催化体系。这些基于两种可商购/易购的铜络合物[CuCl（IPr）]或[CuI（PPh 3）3 ]，它们在低金属负载量下（PPh 3系统）或在没有其他任何添加剂的情况下（IPr系统）。这些系统用于该特定反应的首次报道的机理研究。通过实验/计算DFT方法可以确定（1）一些碘炔在铜催化条件下可能易于脱卤，更重要的是，（2）两种不同的机理途径可能与这些催化剂竞争（通过铜） （III）金属环或通过起始碘炔的直接π-活化。
• Base and concentration effects on the product distribution in copper-promoted alkyne–azide cycloaddition: additive-free route to 5-iodo-triazoles
  作者：Nicholas W. Smith、Bradley P. Polenz、Shawna B. Johnson、Sergei V. Dzyuba

  DOI：10.1016/j.tetlet.2009.11.089

  日期：2010.1

  Formation of 5-iodo-triazoles in CuI-promoted cycloadditions between alkynes and azides is controlled by DMAP and low alkyne concentrations.

  在炔烃和叠氮化物之间的CuI促进的环加成反应中，5-碘代三唑的形成受DMAP和低炔烃浓度的控制。
• Efficient copper-catalyzed tandem oxidative iodination and alkyne-azide cycloaddition in the presence of glycine-type ligands
  作者：Donghe Yuan、Shilei Wang、Gongming Zhu、Anlian Zhu、Lingjun Li

  DOI：10.1016/j.tet.2020.131911

  日期：2021.2

  described that a copper-catalyzed (10 mol%) tandem oxidative iodination and alkyne-azide cycloaddition could be completed in the presence of the newly-found glycine-type ligands with low-cost NaI as the iodine resource. In the novel reaction system, a wide range of terminal alkyne, organic azide and inexpensive iodide could react effectively in one pot to give structurally diverse 5-iodo-1,4-subsitutied 1,2

  串联氧化碘化和炔-叠氮化物环加成反应为制备5-碘-1,2,3-三唑提供了最广泛使用的方法之一。然而，化学计量的铜盐参与这种类型的反应以提高反应效率，这引起了与有毒金属污染和较差的可持续性有关的一些问题。在本文中，我们描述了在以低成本NaI作为碘资源的新发现的甘氨酸型配体的存在下，可以完成铜催化（10 mol％）串联氧化碘化和炔-叠氮化物环加成反应。在新颖的反应系统中，各种各样的末端炔烃，有机叠氮化物和廉价的碘化物可在一个反应​​釜中有效反应，得到结构上多样的5-碘-1,4-取代的1,2,3-三唑。