1-benzyl-4-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole | 1429172-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-4-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole
• CAS: 1429172-06-4
• 化学式: C₂₂H₁₉N₃O
• 分子量: 341.412
• InChiKey: DUJKNGMKFDHJDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1-benzyl-4-(4-methoxyphenyl)-5-phenyl-1H-1,2,3-triazole 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 生成 4-(1-benzyl-5-phenyl-1H-1,2,3-triazol-4-yl)phenol
  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：

  4-乙炔基苯甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium azide 、 碘 、 potassium carbonate 、 三乙胺 、 β-环糊精 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 1-benzyl-4-(4-methoxyphenyl)-5-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

• Copper-Catalyzed Decarboxylative Cycloaddition of Propiolic Acids, Azides, and Arylboronic Acids: Construction of Fully Substituted 1,2,3-Triazoles
  作者：Xiang-Xiang Wang、Yangchun Xin、Yi Li、Wen-Jin Xia、Bin Zhou、Rui-Rong Ye、Ya-Min Li

  DOI：10.1021/acs.joc.9b03285

  日期：2020.3.6

  A copper-catalyzed decarboxylative cycloaddition of propiolic acids, azides, and arylboronic acids is described. The present reaction provides an efficient and convenient method for the synthesis of various fully substituted 1,2,3-triazoles from readily available starting materials. A possible mechanism is proposed.

  描述了丙酸，叠氮化物和芳基硼​​酸的铜催化的脱羧环加成。本反应为从容易获得的起始原料合成各种完全取代的1,2,3-三唑提供了一种有效而方便的方法。提出了一种可能的机制。
• Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles
  作者：Fang Wei、Haoyu Li、Chuanling Song、Yudao Ma、Ling Zhou、Chen-Ho Tung、Zhenghu Xu

  DOI：10.1021/acs.orglett.5b01342

  日期：2015.6.5

  A Cu/Pd-catalyzed, three-component click reaction of azide, alkyne, and aryl halide has been developed. By using this Cu/Pd transmetalation relay catalysis, a variety of 1,4,5-trisubstituted 1,2,3-triazoles were quickly assembled in one step in high yields with complete regioselectivity, just like assembling Lego bricks. Notably, different from the well-established CuAAC click reactions only working on terminal alkynes, this reaction offers an alternative solution for the problem of the click reaction of internal alkynes.
• Pd-catalyzed ligand-free C(5)–H arylation of 1,4-disubstituted 1,2,3-triazoles promoted by microwaves
  作者：Fen Zhao、Wen-Hai Tian、Fang Luo、Hui-Ling Cheng、Yu-Bo Jiang、Zhen Chen

  DOI：10.1080/00397911.2016.1222441

  日期：2016.10.17

  Pd(OAc)(2)-catalyzed regioselective C(5)-H arylation of 1,4-disubstituted 1,2,3-triazoles was achieved without ligand under microwave conditions in 1h, generating 1,4,5-trisubstituted 1,2,3-triazoles with good to excellent yields. The obtained molecules can be easily converted into 4,5-disubstituted 1,2,3-triazoles through the debenzylation process with one-pot manipulation.[GRAPHICS].
• [Cu8(μ4-H){S2P(OEt)2}6](PF6): A Novel Catalytic Hydride-Centered Copper Cluster for Azide-Alkyne Cycloaddtion
  作者：Bo-Han Lee、Cheng-Chieh Wu、Xuan Fang、C. W. Liu、Jia-Liang Zhu

  DOI：10.1007/s10562-013-0993-7

  日期：2013.6

  A hydride-centered dithiophosphate cluster [Cu-8(mu(4)-H)S2P(OEt)(2)}(6)](PF6) (1)] previously developed by us was applied as a new catalyst to the 1,3-dipolar cycloaddition of organic azides and alkynes for preparing substituted trizoles. With the required catalyst loading as low as 0.4 mol%, the reactions of terminal alkynes with BnN3 all proceeded smoothly at ambient temperature in CH3CN to exclusively produce 1,4-triazoles in good yields. For these reactions, it is assumed that the formation of the requisite copper acetylide intermediate is facilitated by the abstraction of the terminal hydrogen of alkynes by the hydride released from the central of the cluster. With only few examples being documented in literatures, the reactions of a range of internal alkynes have also been realized under the catalysis of 1 (0.8 mol%) in DMF at elevated temperature, to yield 1,4,5-trisubstituted triazoles in moderate to high yields. Our study has provided a preliminary insight into the effect of sulfur-based ligands on the activity of copper ion.