1-benzyl-4-decyl-1H-1,2,3-triazole | 1227164-16-0

• 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: 1-benzyl-4-decyl-1H-1,2,3-triazole
• 英文别名: 1-benzyl-4-decyltriazole
• CAS: 1227164-16-0
• 化学式: C₁₉H₂₉N₃
• 分子量: 299.459
• InChiKey: QUQOYEQXTSAKAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  30.7
• 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 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 24.0h， 生成 1-benzyl-4-decyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Chemical synthesis and biological evaluation of triazole derivatives as inhibitors of InhA and antituberculosis agents

  摘要：

  A series of triazoles have been prepared and evaluated as inhibitors of InhA as well as inhibitors of Mycobacterium tuberculosis H37Rv. Several of these new compounds possess a good activity against InhA, particularly compounds 17 and 18 for which molecular docking has been performed. Concerning their activities against M. tuberculosis H37Rv strain, two of them, 3 and 12, were found to be good inhibitors with MIC values of 0.50 and 0.25 mu g/ml, respectively. Particularly, compound 12 presenting the best MIC value of all compounds tested (0.6 mu M) is totally inactive against InhA. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.029

文献信息

• Synthesis and antimycobacterial activity of disubstituted benzyltriazoles
  作者：Frans J. Smit、Ronnett Seldon、Janine Aucamp、Audrey Jordaan、Digby F. Warner、David D. N’Da

  DOI：10.1007/s00044-019-02458-7

  日期：2019.12

  and development of new agents for the treatment of this plight. In search for such drugs, we investigated a series of benzyltriazole derivatives. We herein report the design, synthesis and biological activity of disubstituted benzyltriazoles against the human virulent H37Rv strain of Mtb as well as the toxicity on human embryonic kidney (HEK-293) cells. The derivative 21 featuring trifluoromethyl substituent

  结核分枝杆菌（Mtb）（人结核病（TB）的病原体）的多药耐药菌株的流行不断增加，强烈刺激了发现和开发新的治疗这种疾病的药物。为了寻找此类药物，我们研究了一系列苄基三唑衍生物。我们在本文中报道了二取代的苄基三唑类抗人Mtb的H37Rv强毒株的设计，合成和生物学活性，以及对人胚肾（HEK-293）细胞的毒性。在苯环和n的对位上具有三氟甲基取代基的衍生物21在无白蛋白的培养基中，三唑环上4位的丁基丁基链活性最高，MIC 90和MIC 99分别为1.73和3.2 µM。它还显示出对细菌生长抑制的高度选择性（SI> 58），因此是进一步研究的较好选择，包括铅优化，DMPK参数确定以及在动物模型中对其活性的评估。
• Unsupported Copper Nanoparticles in the 1,3-Dipolar Cycloaddition of Terminal Alkynes and Azides
  作者：Francisco Alonso、Yanina Moglie、Gabriel Radivoy、Miguel Yus

  DOI：10.1002/ejoc.200901446

  日期：2010.4

  Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3-triazoles were prepared in

  发现现成的铜纳米粒子可催化叠氮化物和炔烃的 1,3-偶极环加成，其速率可与微波化学相媲美。纳米颗粒的制备和点击反应都是在温和的条件下进行的，反应时间很短，并且没有任何稳定添加剂或配体。以极好的收率制备了多种 1,2,3-三唑。在不同的反应性研究和氘化实验的基础上假设了一种反应机制。铜(I) 炔化物被证明是真正的中间体。
• Expanding the scope of novel 1,2,3-triazole derivatives as new antiparasitic drug candidates
  作者：Renzo Carlucci、Gabriel Di Gresia、María Gabriela Mediavilla、Julia A. Cricco、Babu L. Tekwani、Shabana I. Khan、Guillermo R. Labadie

  DOI：10.1039/d2md00324d

  日期：——

  prepare new chemical entities for antiparasitic and antituberculosis drug development. In this opportunity a new series of prenyl-1,2,3-triazoles were prepared from isoprenyl azides and different alkynes looking for new antimalarial drug candidates. The compounds were prepared by copper(I) catalyzed dipolar cycloaddition of the isoprenyl azide equilibrium mixture providing exclusively 1,4-disubstituted 1

  我们之前已经表明，异戊二烯和脂肪族三唑是制备用于抗寄生虫和抗结核药物开发的新化学实体的有趣基序。借此机会，由异戊二烯基叠氮化物和不同的炔烃制备了一系列新的异戊二烯基-1,2,3-三唑，以寻找新的抗疟药物候选物。该化合物通过铜( I )催化的异戊二烯基叠氮化物平衡混合物的偶极环加成反应制备，以区域特异性方式专门提供1,4-二取代的1,2,3-三唑。对氯喹敏感（CQ 敏感）的塞拉利昂 (D6) 和氯喹耐药的印度支那 (W2) 恶性疟原​​虫菌株以及之前未报道过的那些化合物也测试了 64 种化合物的完整集合。杜氏利什曼原虫，内脏利什曼病的病原体。13 种类似物显示出 IC 50低于 10 μM 的抗疟活性，而新报道的类似物的抗利什曼活性与之前报道的类似物相比没有改善。化合物1o和1r被确定为最有前途的抗疟药物先导化合物，对于具有高选择性指数的 CQ 敏感和耐药恶性疟原虫菌株， IC 50均低于 3
• Synthesis and structure–activity relationship of 1- and 2-substituted-1,2,3-triazole letrozole-based analogues as aromatase inhibitors
  作者：Jérémie Doiron、Al Haliffa Soultan、Ryan Richard、Mamadou Mansour Touré、Nadia Picot、Rémi Richard、Miroslava Čuperlović-Culf、Gilles A. Robichaud、Mohamed Touaibia

  DOI：10.1016/j.ejmech.2011.05.074

  日期：2011.9

  A series of bis- and mono-benzonitrile or phenyl analogues of letrozole 1, bearing (1,2,3 and 1,2,5)-triazole or imidazole, were synthesized and screened for their anti-aromatase activities. The unsubstituted 1,2,3-triazole 10a derivative displayed inhibitory activity comparable with that of the aromatase inhibitor, letrozole I. Compound 10a, bearing a 1,2,3-triazole, is also 10000-times more tightly binding than the corresponding analogue 25 bearing a 1,2,5-triazole, which confirms the importance of a nitrogen atom at position 3 or 4 of the 5-membered ring needed for high activity. The effect on human epithelial adrenocortical carcinoma cell line (H295R) proliferation was also evaluated. The compound 10j (IC50 = 4.64 mu M), a letrozole 1 analogue bearing para-cyanophenoxymethylene-1,2,3-triazole decreased proliferation rates of H295R cells by 76 and 99% in 24 and 72 h respectively. Computer calculations, using quantum ab initio structures, suggest a possible correlation between anti-aromatase activity and the distance between the nitrogen in position 3 or 4 of triazole nitrogen and the cyano group nitrogen. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Huisgen click cycloadditions from a copper(II)-tren precatalyst without external sacrificial reductant
  作者：Lydie Harmand、Marie-Hélène Lescure、Nicolas Candelon、Mathieu Duttine、Dominique Lastécouères、Jean-Marc Vincent

  DOI：10.1016/j.tetlet.2012.01.035

  日期：2012.3

  The copper(II) complex [Cu(C18(6)tren)](Br)(2), 2, is an efficient precatalyst for the Huisgen 'click' cycloaddtion which can be used at low loading without the requirement of an external sacrificial reductant such as sodium ascorbate. EPR studies support the in situ reduction of 2 by the alkyne to generate a reactive copper(1) catalyst. (C) 2012 Elsevier Ltd. All rights reserved.