3-叠氮基联苯 | 14213-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-叠氮基联苯
• 英文名称: 1-azido-3-phenylbenzene
• 英文别名: biphenyl-3-ylazide；3-azidobiphenyl；3-Azido-biphenyl；1,1'-Biphenyl, 3-azido-
• CAS: 14213-01-5
• 化学式: C₁₂H₉N₃
• 分子量: 195.224
• InChiKey: RFTRNOXIKPDOOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-叠氮基联苯 在 manganese(IV) oxide 、 palladium 10% on activated carbon 、 氢气 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (2-aminophenyl)(1-(biphenyl-3-yl)-1H-1,2,3-triazol-4-yl)methanone
  参考文献：
  名称：

  1-Phenyl-4-benzoyl-1H-1,2,3-triazoles as Orally Bioavailable Transcriptional Function Suppressors of Estrogen-Related Receptor α

  摘要：

  Estrogen-related receptor a is a potential candidate target for therapeutic treatment of breast cancer. We describe the discovery and structure activity relationship study of a series of 1-phenyl-4-benzoyl-1H-1,2,3-triazoles as novel suppressors of ERR alpha transcriptional functions. The most promising compound, 2-aminophenyl-(1-(3-isopropylpheny1)-1H-1,2,3-triazol-4-yl)methanone (14n), potently suppressed the transcriptional functions of ERR alpha with IC50 = 0.021 mu M in a cell-based reporter gene assay and also decreased both the mRNA levels and the protein levels of ERR alpha and the downstream targets. This compound inhibited the proliferation and migration of breast cancer cells with high level of ERR alpha. Preliminary pharmacolcinetic studies suggested that it possessed a good pharmacokinetic profile with an oral bioavailability of 71.8%. The compounds may serve as novel small molecule probes for further validation of ERR alpha as a molecular target for anticancer drug development.

  DOI：

  10.1021/jm4003928
• 作为产物：
  描述：

  3-联苯硼酸 在 sodium azide 、 copper diacetate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以46%的产率得到3-叠氮基联苯
  参考文献：
  名称：

  铜 (II) 催化芳基/杂芳基硼酸、硼酸盐和三氟硼酸盐转化为相应的叠氮化物：底物范围和限制

  摘要：

  我们报告了铜 (II) 催化的有机硼化合物转化为相应的叠氮化物衍生物。评估了一系列系统的苯基硼酸衍生物，以检查取代基的空间和电子效应对反应产率以及官能团兼容性的重要性。杂环底物也被证明参与了这种温和的反应，而结合了 BC( sp³) 键在反应条件下不反应。铜 (II) 催化的硼酸-叠氮化物偶联反应进一步扩展到硼酸酯和有机三氟硼酸钾盐。本文描述的方法补充了从各自的氨基、三氮烯和卤化物衍生物制备芳基叠氮化物的现有程序，我们预计它将极大地促进铜和钌催化的叠氮化物-炔环加成反应，以制备多种功能化的 1-芳基-或1-杂芳基-1,2,3-三唑衍生物。 叠氮化物 - 有机硼化合物 - 铜催化 - 1,2,3-三唑

  DOI：

  10.1055/s-0029-1218683

文献信息

• Click Reaction as a Tool to Combine Pharmacophores: The Case of Vismodegib
  作者：Michael S. Christodoulou、Mattia Mori、Rebecca Pantano、Romina Alfonsi、Paola Infante、Maurizio Botta、Giovanna Damia、Francesca Ricci、Panagiota A. Sotiropoulou、Sandra Liekens、Bruno Botta、Daniele Passarella

  DOI：10.1002/cplu.201402435

  日期：2015.6

  obtain a new class of Hedgehog pathway inhibitors. The smoothened protein is part of the hedgehog signaling pathway that is inhibited by the lead compound Vismodegib. Based on molecular modeling simulations, seven triazole derivatives of Vismodegib are synthesized and their biological effect on different endothelial, cancer, and cancer stem cell lines is reported.

  据报道，设计和制备了一个小的1,4-二苯基-1,2,3-三唑衍生物文库，目的是获得一类新的Hedgehog途径抑制剂。平滑化的蛋白质是被前导化合物Vismodegib抑制的hedgehog信号通路的一部分。基于分子模拟，合成了维斯莫德单抗的七种三唑衍生物，并报道了它们对不同的内皮细胞，癌症和癌症干细胞系的生物学作用。
• Three‐Component Coupling of α‐Trifluoromethyl Carbonyls, Azides and Amines for the Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazoles
  作者：Ge Gao、Kuantao、Mao、Leiyang Lv、Zhiping Li

  DOI：10.1002/adsc.202200094

  日期：2022.4.12

  A metal-free three-component coupling of α-CF3 carbonyls, azides and amines for the regioselective synthesis of 1,4,5-trisubstituted 1,2,3-triazoles in the air is established. Various substituted 4-amide 1,2,3-triazoles were obtained when the enolizable α-CF3 ketones were applied in aqueous reaction medium. Control and 18O-labelling experiments revealed that the in situ generated β-oxo amide was responsible

  建立了α-CF 3羰基、叠氮化物和胺的无金属三组分偶联，用于在空气中区域选择性合成1,4,5-三取代的1,2,3-三唑。当将可烯醇化的α-CF 3酮应用于水性反应介质时，获得了各种取代的4-酰胺1,2,3-三唑。对照和18 O-标记实验表明，原位生成的 β-氧代酰胺负责形式上的氧转移和随后的 [3+2] 环加成反应，胺作为催化剂和反应物。在非烯醇化α-CF 3的情况下酯类中，仅实现了密集官能化的5-氨基1,2,3-三唑，这可以实现复杂生物分子的后期官能化。
• A Photochemical Strategy for <i>ortho</i>‐Aminophenol Synthesis via Dearomative‐Rearomative Coupling Between Aryl Azides and Alcohols
  作者：Bo Li、Alessandro Ruffoni、Daniele Leonori

  DOI：10.1002/anie.202310540

  日期：2023.12.21

  Photolysis of aryl azides with purple light in the presence of alcohols enables the direct preparation of challenging ortho-aminophenols. The process goes via a singlet nitrene-mediated dearomative-rearomative cascade that enables introduction of the alcohol in place of the azide and shifts the amino group to its ortho-position.

  在醇存在下用紫光光解芳基叠氮化物可以直接制备具有挑战性的邻氨基苯酚。该过程通过单线态氮烯介导的脱芳香-重芳香级联进行，该级联能够引入醇代替叠氮化物并将氨基转移至其邻位。
• Iridium nitrenoid-enabled arene C−H functionalization
  作者：Liang-Wen Qi、Torben Rogge、K. N. Houk、Yixin Lu

  DOI：10.1038/s41929-024-01207-3

  日期：——

  Direct arene C−H functionalization via nucleophilic aromatic substitution remains a challenging task. Here we report an iridium nitrenoid-catalysed arene C−H functionalization strategy, making use of readily available aryl azides as electrophiles to react with different nucleophilic reaction partners. The practicality of this methodology is demonstrated by enantioselective synthesis of chiral 2-amino-2′-hydroxy-1

  通过亲核芳香取代直接芳烃 C−H 官能化仍然是一项具有挑战性的任务。在这里，我们报告了一种铱氮烯基催化芳烃 C−H 官能化策略，利用容易获得的芳基叠氮化物作为亲电子试剂与不同的亲核反应伙伴发生反应。使用 β-萘酚和 β-萘基叠氮化物对映选择性合成手性 2-氨基-2'-羟基-1,1'-联萘（一类不对称转化中的结构单元、配体和催化剂）证明了该方法的实用性在定制的恶唑啉螯合铱络合物的催化下作为起始材料。机理研究和密度泛函理论计算表明，该反应通过铱氮介导的 C−H 官能化途径进行。报道的芳烃CH官能化策略可以作为扩展亲核芳香取代反应的适用性的蓝图，对于含苯胺分子的合成特别有价值。
• Small Molecule Inhibition of MicroRNA miR-21 Rescues Chemosensitivity of Renal-Cell Carcinoma to Topotecan
  作者：Yuta Naro、Nicholas Ankenbruck、Meryl Thomas、Yaniv Tivon、Colleen M. Connelly、Laura Gardner、Alexander Deiters

  DOI：10.1021/acs.jmedchem.7b01891

  日期：2018.7.26

  Chemical probes of microRNA (miRNA) function are potential tools for understanding miRNA biology that also provide new approaches for discovering therapeutics for miRNA-associated diseases. MicroRNA-21 (miR-21) is an oncogenic miRNA that is overexpressed in most cancers and has been strongly associated with driving chemoresistance in cancers such as renal cell carcinoma (RCC). Using a cell-based luciferase reporter assay to screen small molecules, we identified a novel inhibitor of miR-21 function. Following structure-activity relationship studies, an optimized lead compound demonstrated cytotoxicity in several cancer cell lines. In a chemoresistant-RCC cell line, inhibition of miR-21 via small molecule treatment rescued the expression of tumor-suppressor proteins and sensitized cells to topotecan-induced apoptosis. This resulted in a > 10-fold improvement in topotecan activity in cell viability and clonogenic assays. Overall, this work reports a novel small molecule inhibitor for perturbing miR-21 function and demonstrates an approach to enhancing the potency of chemotherapeutics specifically for cancers derived from oncomir addiction.