1-(2-hydroxybenzyl)-4-phenyl-1H-1,2,3-triazole | 860653-77-6

• 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-(2-hydroxybenzyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 2‐((4‐phenyl‐1H‐1,2,3‐triazol‐1‐yl)methyl)phenol；2-[(4-Phenyltriazol-1-yl)methyl]phenol
• CAS: 860653-77-6
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: YWRYSMHDUJJFRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  50.94
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxybenzyl)-4-phenyl-1H-1,2,3-triazole 、 (R)-5,5',6,6'-tetramethyl-[1,1'-biphenyl]-2,2'-diol 在 三乙胺 、 三氯化磷 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到
  参考文献：
  名称：

  Click-Connected Ligand Scaffolds:  Macrocyclic Chelates for Asymmetric Hydrogenation

  摘要：

  Click chemistry is used to construct ligand scaffolds for a series of chiral diphosphites. Enantioselectivity as high as 97% ee is obtained using these click ligands in rhodium-catalyzed asymmetric hydrogenation. Control experiments and spectroscopic data suggest that a 16-membered PP-macrocyclic Rh(I) chelate is formed.

  DOI：

  10.1021/ol702890s
• 作为产物：
  描述：

  1-(叠氮甲基)-2-甲氧基苯 在 三溴化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 27.0h， 生成 1-(2-hydroxybenzyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  1,4- and 2,4-substituted-1,2,3-triazoles as potential potassium channel activators. VII

  摘要：

  New 1,4- and 2,4-substituted 1,2,3-triazole derivatives were synthesized and tested as potential BK(Ca) channel openers, as a part of a research program, which hypothesizes a pharmacophoric structure containing the 1,2,3-triazole ring. The structure-activity relationships were studied introducing some structural changes concerning molecular geometry and the presence of a hydrogen bond donor as a primary amino group and a phenolic or alcoholic hydroxy function. The compounds were prepared by nucleophilic substitution on the 1,2,3-triazole ring and by 1,3-dipolar cycloaddition of azides to selected alkynes and to phenylacetone. The new compounds tested on rat aortic rings did not exhibit any significant vasorelaxing activity.

  DOI：

  10.1016/j.farmac.2005.03.004

文献信息

• Exploring the chemical space of 1,2,3-triazolyl triclosan analogs for discovery of new antileishmanial chemotherapeutic agents
  作者：Julia Fernández de Luco、Alejandro I. Recio-Balsells、Diego G. Ghiano、Ana Bortolotti、Juán Manuel Belardinelli、Nina Liu、Pascal Hoffmann、Christian Lherbet、Peter J. Tonge、Babu Tekwani、Héctor R. Morbidoni、Guillermo R. Labadie

  DOI：10.1039/d0md00291g

  日期：——

  were designed in search of novel structures with leishmanicidal activity and prepared using different alkynes and azides. The 37 compounds were assayed against Leishmania donovani, the etiological agent of leishmaniasis, yielding some analogs with activity at micromolar concentrations and against M. tuberculosis H37Rv resulting in scarce active compounds with an MIC of 20 μM. To study the mechanism

  三氯生和异烟肼是已知的抗结核化合物，已被证明对利什曼原虫也有活性。基于这些理由，设计了基于抗结核分子三氯生和 5-辛基-2-苯氧基苯酚 (8PP) 的 37 种不同的 1,2,3-三唑的集合，以寻找具有杀利什曼原虫活性的新型结构，并使用不同的炔烃和叠氮化物制备. 对 37 种化合物进行了针对多诺瓦利什曼原虫（利什曼病的病原体）的分析，产生了一些具有微摩尔浓度活性的类似物，并针对结核分枝杆菌H37Rv 产生了 MIC 为 20 μM 的稀有活性化合物。为了研究这些儿茶酚的作用机制，我们分析了文库对结核分枝杆菌烯酰-ACP 还原酶 (ENR) InhA，对该酶的抑制作用较差。还测试了对 Vero 细胞的细胞毒性，结果在高达 20 μM 的浓度下没有任何化合物具有细胞毒性。衍生物5f可被视为未来抗利什曼病药物开发的宝贵起点。需要进一步研究推定的利什曼原虫 InhA 直向同源物作为治疗靶点的验证。