2-(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)propan-2-ol | 856863-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)propan-2-ol
• 英文别名: 2-[1-(4-Nitrophenyl)triazol-4-yl]propan-2-ol
• CAS: 856863-41-7
• 化学式: C₁₁H₁₂N₄O₃
• mdl: MFCD25975789
• 分子量: 248.241
• InChiKey: BWDADZDXVSSGHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯胺 在 盐酸 、 sodium azide 、 copper diacetate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 2-(1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)propan-2-ol
  参考文献：
  名称：

  1,2,3-三唑衍生物的合成和对念珠菌菌株的体外抗真菌评价

  摘要：

  1,2,3-三唑作为具有重要生物活性的化合物已被广泛研究。在这项工作中，我们描述了通过铜催化的叠氮化炔环加成（CuAAc 或点击化学）合成十种 2-(1-aryl-1H-1,2,3-triazol-4-yl)propan-2-ols。接下来，使用微量稀释肉汤法对四种不同念珠菌属的 42 株分离物评估了这十种化合物的体外抗真菌活性。在所有测试的化合物中，卤素取代的三唑 2-[1-(4-氯苯基)-1H-(1,2,3)triazol-4-yl]propan-2-ol 显示出最好的抗真菌特性，表明进一步可以对结构进行修改，以在未来获得更好的候选药物。

  DOI：

  10.3390/molecules17055882

文献信息

• Synthesis of 1,2,3-Triazole Derivatives and in Vitro Antifungal Evaluation on Candida Strains
  作者：Reginaldo G. Lima-Neto、Nery N. M. Cavalcante、Rajendra M. Srivastava、Francisco J. B. Mendonça Junior、Almir G. Wanderley、Rejane P. Neves、Janaína V. dos Anjos

  DOI：10.3390/molecules17055882

  日期：——

  1,2,3-Triazoles have been extensively studied as compounds possessing important biological activities. In this work, we describe the synthesis of ten 2-(1-aryl-1H-1,2,3-triazol-4-yl)propan-2-ols via copper catalyzed azide alkyne cycloaddition (CuAAc or click chemistry). Next thein vitro antifungal activity of these ten compounds was evaluated using the microdilution broth method against 42 isolates

  1,2,3-三唑作为具有重要生物活性的化合物已被广泛研究。在这项工作中，我们描述了通过铜催化的叠氮化炔环加成（CuAAc 或点击化学）合成十种 2-(1-aryl-1H-1,2,3-triazol-4-yl)propan-2-ols。接下来，使用微量稀释肉汤法对四种不同念珠菌属的 42 株分离物评估了这十种化合物的体外抗真菌活性。在所有测试的化合物中，卤素取代的三唑 2-[1-(4-氯苯基)-1H-(1,2,3)triazol-4-yl]propan-2-ol 显示出最好的抗真菌特性，表明进一步可以对结构进行修改，以在未来获得更好的候选药物。
• A Cu(I)-promoted one-pot ‘SNAr–click reaction’ of fluoronitrobenzenes
  作者：Kulbhushan A. Dururgkar、Rajesh G. Gonnade、C.V. Ramana

  DOI：10.1016/j.tet.2009.03.035

  日期：2009.5

  A one-pot two-step sequence involving a nucleophilic aromatic substitution (SNAF) of activated fluorobenzenes with azide nucleophile and in situ Huisgen cycloaddition of the resulting aryl azides with alkynes has been developed for a rapid access to 1,4-substituted triazoles. Control experiments revealed that both the steps are catalyzed by Cu(I) and also the course of reaction as SNAr followed by [3+2]-cycloaddition. (C) 2009 Elsevier Ltd. All rights reserved.
• Preliminary investigations into triazole derived androgen receptor antagonists
  作者：Jarrad M. Altimari、Birunthi Niranjan、Gail P. Risbridger、Stephanie S. Schweiker、Anna E. Lohning、Luke C. Henderson

  DOI：10.1016/j.bmc.2014.03.018

  日期：2014.5

  A range of 1,4-substituted-1,2,3-N-phenyltriazoles were synthesized and evaluated as non-steroidal androgen receptor (AR) antagonists. The motivation for this study was to replace the N-phenyl amide portion of small molecule antiandrogens with a 1,2,3-triazole and determine effects, if any, on biological activity. The synthetic methodology presented herein is robust, high yielding and extremely rapid. Using this methodology a series of 17 N-aryl triazoles were synthesized from commercially available starting materials in less than 3 h. After preliminary biological screening at 20 and 40 mu M, the most promising three compounds were found to display IC50 values of 40-50 mu M against androgen dependent (LNCaP) cells and serve as a starting point for further structure-activity investigations. All compounds in this work were the focus of an in silico study to dock the compounds into the human androgen receptor ligand binding domain (hARLBD) and compare their predicted binding affinity with known antiandrogens. A comparison of receptor-ligand interactions for the wild type and T877A mutant AR revealed two novel polar interactions. One with Q738 of the wild type site and the second with the mutated A877 residue. (C) 2014 Elsevier Ltd. All rights reserved.