2-(4-phenyl-1H-1,2,3-triazol-1-yl)phenylmethanol | 1237588-36-1

• 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-(4-phenyl-1H-1,2,3-triazol-1-yl)phenylmethanol
• 英文别名: 1-(o-hydroxytolyl)-4-phenyl-1,2,3-triazole
• CAS: 1237588-36-1
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: ZERWCYYJHCRKSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 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：

  2-(4-phenyl-1H-1,2,3-triazol-1-yl)phenylmethanol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以90%的产率得到2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of phenyl-1H-1,2,3-triazole derivatives as anti-inflammatory agents

  摘要：

  Rapid and efficient synthesis of a phenyl-1H-1,2,3-triazole library enabled cost-effective biological testing of a range of novel non-steroidal anti-inflammatory drugs with potential for improved drug efficacy and toxicity profiles. Anti-inflammatory activities of the phenyl-1H-1,2,3-triazole analogs synthesized in this report were assessed using the xylene-induced ear edema model in mice. At least four analogs, 2a, 2b, 2c, and 4a, showed more potent effects than the reference anti-inflammatory drug diclofenac at the same dose of 25 mg/kg. To explore relationships between the structural properties of phenyl-1H-1,2,3-triazole analogs and their anti-inflammatory activities in xylene-induced ear edema, comparative molecular field analysis was performed, and pharmacophores showing good anti-inflammatory activities were identified based on an analysis of contour maps obtained from comparative molecular field analysis. The anti-inflammatory effect on the molecular level was tested by the expression of tumor necrosis factor-alpha induced COX-2 using Western blots. Because the addition of the analog 2c caused the expression change of TNF-alpha induced COX-2, the molecular binding mode between 2c and COX-2 was elucidated using in silico docking. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.01.003
• 作为产物：
  描述：

  邻氨基苯甲醇 在 copper(ll) sulfate pentahydrate 、 硫酸 、 sodium ascorbate 、 sodium nitrite 作用下， 以 水 、 异丙醇 为溶剂， 反应 20.5h， 生成 2-(4-phenyl-1H-1,2,3-triazol-1-yl)phenylmethanol
  参考文献：
  名称：

  Synthesis and biological evaluation of phenyl-1H-1,2,3-triazole derivatives as anti-inflammatory agents

  摘要：

  Rapid and efficient synthesis of a phenyl-1H-1,2,3-triazole library enabled cost-effective biological testing of a range of novel non-steroidal anti-inflammatory drugs with potential for improved drug efficacy and toxicity profiles. Anti-inflammatory activities of the phenyl-1H-1,2,3-triazole analogs synthesized in this report were assessed using the xylene-induced ear edema model in mice. At least four analogs, 2a, 2b, 2c, and 4a, showed more potent effects than the reference anti-inflammatory drug diclofenac at the same dose of 25 mg/kg. To explore relationships between the structural properties of phenyl-1H-1,2,3-triazole analogs and their anti-inflammatory activities in xylene-induced ear edema, comparative molecular field analysis was performed, and pharmacophores showing good anti-inflammatory activities were identified based on an analysis of contour maps obtained from comparative molecular field analysis. The anti-inflammatory effect on the molecular level was tested by the expression of tumor necrosis factor-alpha induced COX-2 using Western blots. Because the addition of the analog 2c caused the expression change of TNF-alpha induced COX-2, the molecular binding mode between 2c and COX-2 was elucidated using in silico docking. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.01.003

文献信息

• Synthesis of 5-Iodo-1,2,3-triazoles from Organic Azides and Terminal Alkynes­: Ligand Acceleration Effect, Substrate Scope, and Mechanistic Insights
  作者：Lei Zhu、David Barsoum、Christopher Brassard、Jason Deeb、Najeah Okashah、Kesavapillai Sreenath、J. Simmons

  DOI：10.1055/s-0033-1339312

  日期：——

  established conditions for the reaction. An improved method has been developed for the preparation of 5-iodo-1,2,3-triazoles directly from organic azides and terminal alkynes by a reaction mediated by copper(I) and iodinating agents generated in situ. The major methodological advance of the current procedure is that it provides a high conversion and good iodo/proto selectivity with a broad range of substrates

  摘要 已经开发出一种改进的方法，该方法通过由铜（I）和原位生成的碘化剂介导的反应，直接从有机叠氮化物和末端炔烃制备5-碘-1,2,3-三唑。当前方法的主要方法学进步在于，它无需使用过量的炔烃即可提供高转化率和良好的碘/原型选择性，并具有广泛的底物，这是先前方法所必需的。加速配体的使用对于成功完成涉及未反应的叠氮化物或炔烃的反应至关重要。提供了新的机理见解，包括证实在确定的反应条件下形成了1-碘炔烃作为关键中间体。 已经开发出一种改进的方法，该方法通过由铜（I）和原位生成的碘化剂介导的反应，直接从有机叠氮化物和末端炔烃制备5-碘-1,2,3-三唑。当前方法的主要方法学进步在于，它无需使用过量的炔烃即可提供高转化率和良好的碘/原型选择性，并具有广泛的底物，这是先前方法所必需的。加速配体的使用对于成功完成涉及未反应的叠氮化物或炔烃的反应至关重要。提供了新的机理见解，包括证实在确定的反应条件下形成了1-碘炔烃作为关键中间体。
• Bimetallic Cu/Pd-catalyzed three-component azide–alkyne cycloaddition/isocyanide insertion: synthesis of fully decorated tricyclic triazoles
  作者：K. Shiva Kumar、Praveen Kumar Naikawadi、Ramanna Jatoth、Rambabu Dandela

  DOI：10.1039/c9ob01175g

  日期：——

  The construction of fully decorated 1,2,3-triazoles has been disclosed via a bimetallic relay-catalyzed cascade process combining azide–alkyne cycloaddition, C(sp²)–H functionalization of 1,2,3-triazoles and isocyanide insertion.

  通过双金属继电器催化的级联反应，结合了偶氮-炔环加成、1,2,3-三唑的C(sp2)-H官能化和异腈插入，披露了完全装饰的1,2,3-三唑的构建方法。
• 1,3-噁嗪并1,2,3-三氮唑类衍生物及其合成 方法与应用
  申请人：昆明理工大学

  公开号：CN110423239B

  公开（公告）日：2021-10-26

  本发明公开了1,3‑噁嗪并1,2,3‑三氮唑类衍生物及其合成方法与应用，属于农药及有机合成技术领域。本发明1,3‑噁嗪并1,2,3‑三氮唑类衍生物的结构式为或其中，R1为H、Me或Cl，R2为Cl、Br、F或Me，R3为吡啶基或噻吩基；本发明以1‑邻羟甲芳基‑4‑芳基‑1,2,3‑三氮唑为原料，在“过渡金属/氧化剂”体系催化下发生选择性碳‑氧偶联反应，选择性生成1,3‑噁嗪并1,2,3‑三氮唑衍生物。本发明1,3‑噁嗪并1,2,3‑三氮唑类衍生物同时含有噁嗪及1,2,3‑三氮唑环结构单元，对三七根腐病致病菌具有很好的抑制效果。
• Copper-Catalyzed Intramolecular C–H Alkoxylation of Diaryltriazoles: Synthesis of Tricyclic Triazole Benzoxazines
  作者：Xinyuan Ma、Haotian Li、Hong Xin、Weigen Du、Edward A. Anderson、Xian Dong、Yubo Jiang

  DOI：10.1021/acs.orglett.0c01517

  日期：2020.7.17

  An efficient copper-catalyzed intramolecular C-H alkoxylation of 1,4-disubstituted 1,2,3-triazoles has been developed. The chemistry was applied to a wide range of substrates, generating tricyclic benzoxazine-fused 1,2,3-triazoles in good yields. Mechanistic studies suggest that a radical pathway may be involved in this transformation. The triazole products were found to exhibit strong antifungal activity against ginseng root-rot disease, demonstrating their potential as a scaffold in medicinal chemistry research.
• Identification of novel F508del-CFTR traffic correctors among triazole derivatives
  作者：Mafalda Bacalhau、Filipa C. Ferreira、Arthur Kmit、Felipe R. Souza、Verônica D. da Silva、André S. Pimentel、Margarida D. Amaral、Camilla D. Buarque、Miquéias Lopes-Pacheco

  DOI：10.1016/j.ejphar.2022.175396

  日期：2023.1