9-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-9H-carbazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-9H-carbazole
• 英文别名: 9-[(1-Benzyltriazol-4-yl)methyl]carbazole；9-[(1-benzyltriazol-4-yl)methyl]carbazole
• 化学式: C₂₂H₁₈N₄
• 分子量: 338.412
• InChiKey: LAWZTVGUYIDCMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 9-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-9H-carbazole
  参考文献：
  名称：

  咔唑衍生物的设计，合成及抗真菌活性

  摘要：

  侵袭性真菌感染的发生率正在迅速增加。临床上可用的抗真菌药具有有限的疗效和严重的耐药性。迫切需要用新型化学支架来发现抗真菌的铅化合物。在我们先前确定的四氢咔唑抗真菌剂的基础上，通过修饰支架和侧链进一步探索了结构与活性之间的关系。几种目标化合物显示出针对念珠菌的有效活性。特别是，化合物13i显示出比先导化合物更好的抗真菌活性，可以用作进一步优化的良好起点。

  DOI：

  10.1016/j.cclet.2013.10.022

文献信息

• Design, synthesis and antifungal activity of carbazole derivatives
  作者：Shi-Ping Zhu、Wen-Ya Wang、Kun Fang、Zheng-Gang Li、Guo-Qiang Dong、Zhen-Yuan Miao、Jian-Zhong Yao、Wan-Nian Zhang、Chun-Quan Sheng

  DOI：10.1016/j.cclet.2013.10.022

  日期：2014.2

  antifungal leads, the structure–activity relationship was further explored by modifying the scaffold and the side chains. Several targeted compounds showed potent activity against Candida species. Particularly, compound 13i showed better antifungal activity than the lead compound, which can be used as a good starting point for further optimization.

  侵袭性真菌感染的发生率正在迅速增加。临床上可用的抗真菌药具有有限的疗效和严重的耐药性。迫切需要用新型化学支架来发现抗真菌的铅化合物。在我们先前确定的四氢咔唑抗真菌剂的基础上，通过修饰支架和侧链进一步探索了结构与活性之间的关系。几种目标化合物显示出针对念珠菌的有效活性。特别是，化合物13i显示出比先导化合物更好的抗真菌活性，可以用作进一步优化的良好起点。
• ‘Quick CuAAC’ Chemistry for Hg(II) and Mn(II) ion sensing via 9H-carbazole derivatives
  作者：Alisha Rani、Parveen Saini、Gurjaspreet Singh、Sushma、Harminder Singh、Gurpreet Kaur、Jandeep Singh

  DOI：10.1016/j.ica.2021.120560

  日期：2021.11

  3-triazole merged 9H–carbazole derivative is being reported with excellent yield but drastic reduction in the reaction time. The 1,2,3-triazole linker has been synthesized under thermal conditions within 20 min and yield of more than 90%, using Cu(I) as catalyst. Using UV–Vis spectral technique, the alkyne product displayed excellent detection capability towards Hg(II) and Mn(II) ions in methanol with the

  据报道，1,2,3-三唑合并的 9H-咔唑衍生物的合成具有优异的产率，但反应时间急剧减少。使用 Cu(I) 作为催化剂，1,2,3-三唑连接体在热条件下在 20 分钟内合成，产率超过 90%。使用紫外-可见光谱技术，炔烃产物对甲醇中的 Hg(II) 和 Mn(II) 离子显示出出色的检测能力，检测限分别低至 20 µM 和 10 µM，而三唑基产物可以有效地检测 Cu （二）离子。
• Copper(I) Catalyzed Azide-Alkyne Click Reaction: Synthesis and Metal-Ion Binding Studies of Some 1,2,3-Triazole Derivatives
  作者：Harinder Singh、Vinod Kumar

  DOI：10.14233/ajchem.2016.19431

  日期：——

  Click chemistry involving 1,3-dipolar cycloaddition reaction of an azide and a terminal alkyne has gained much attention in the field of science to design new materials for various applications. Recently, ability of 1,2,3-triazole ring to participate in complexation with metal ions has been recognized. The demand for selective receptors for specific cations especially sensors that monitor toxic heavy metal ions selectively have been continuously increasing. Therefore, we report herein, the synthesis of some 1,2,3-triazole derivatives through the click reaction. All the newly synthesized compounds thus obtained have been characterized by IR, 1H NMR, 13C NMR and mass spectral studies and screened for their recognition properties towards various metal ions.

  点击化学涉及叠氮化物和末端炔烃的 1,3-二极环加成反应，在设计各种应用新材料的科学领域备受关注。最近，1,2,3-三唑环参与金属离子络合的能力得到了认可。对特定阳离子的选择性受体，尤其是选择性监测有毒重金属离子的传感器的需求不断增加。因此，我们在此报告通过点击反应合成了一些 1,2,3-三唑衍生物。我们通过红外光谱、1H NMR、13C NMR 和质谱研究对所有新合成的化合物进行了表征，并筛选了它们对各种金属离子的识别特性。
• 9<i>H</i>-Carbazole Derivatives Containing the<i>N</i>-Benzyl-1,2,3-triazole Moiety as New Acetylcholinesterase Inhibitors
  作者：Hamidreza Akrami、Bibi F. Mirjalili、Mehdi Khoobi、Alireza Moradi、Hamid Nadri、Saeed Emami、Alireza Foroumadi、Mohsen Vosooghi、Abbas Shafiee

  DOI：10.1002/ardp.201400365

  日期：2015.5

  A series of triazole‐containing carbazole derivatives were designed as new anti‐acetylcholinesterase (AChE) agents. The target compounds 6a–q were simply prepared via a one‐pot three‐component click reaction of N‐propargyl‐9H‐carbazole, sodium azide, and an appropriate benzyl halide. The in vitro anti‐cholinesterase assay showed that the unsubstituted benzyl derivative 6p along with the 2‐F, 2‐Me,

  一系列含三唑的咔唑衍生物被设计为新型抗乙酰胆碱酯酶 (AChE) 药物。通过N-炔丙基-9H-咔唑、叠氮化钠和适当的苄基卤的一锅三组分点击反应简单地制备了目标化合物6a-q。体外抗胆碱酯酶试验表明，未取代的苄基衍生物 6p 以及 2-F、2-Me、3-Me、3-MeO 和 3-F 类似物（6a、6c 和 6g-i）具有显着的抗胆碱酯酶活性。抗 AChE 活性（IC50 ≤ 3.8 μM）。其中，IC50值为1.9 μM的2-甲基苄基衍生物6c是活性最强的化合物。SAR 研究表明，在苄基悬垂基团的邻位或间位上的小卤素原子（如氟原子）或供电子基团（如甲基或甲氧基）可以耐受或提高抗 AChE 活性。
• Synthesis and antimicrobial evaluation of 1,4-disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties
  作者：C. P. Kaushik、Krishan Kumar、Kashmiri Lal、Balasubramanian Narasimhan、Ashwani Kumar

  DOI：10.1007/s00706-015-1544-2

  日期：2016.4

  Synthesis of a small library of 1,4-disubstituted 1,2,3-triazoles containing benzofused N-heteroaromatic moieties was carried out through click reaction of various benzofused N-heteroaromatic alkynes with aromatic azides. All the synthesized compounds were characterized by spectroscopic techniques like IR, H-1 NMR, C-13 NMR, mass spectrometry and evaluated in vitro for antimicrobial activity against two Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus), one Gram-negative bacteria (Escherichia coli) and two fungi (Candida albicans, Aspergillus niger). Most of the synthesized 1,4-disubstituted 1,2,3-triazoles were found to possess significant antibacterial and antifungal activity against tested microbial species. Moreover, docking simulation of the compound 1-[(1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl)methyl]-1H-benzo[d]imidazole was also carried out against E. coli topoisomerase II DNA gyrase B enzyme to study the binding modes and mechanism of action.