4-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzonitrile | 1126635-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzonitrile
• 英文别名: 4-[4-(Hydroxymethyl)triazol-1-yl]benzonitrile
• CAS: 1126635-75-3
• 化学式: C₁₀H₈N₄O
• 分子量: 200.2
• InChiKey: XDOVLYBJGJLNMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzonitrile 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 4-(4-甲酰基三唑-1-基)苯甲腈
  参考文献：
  名称：

  “Click” Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)

  摘要：

  Unsymmetrically 1,1'-disubstituted 4,4'-bis-1H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole intermediates 5: (a) the stepwise Swern oxidation/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadlyne 9. The method is highlighted by its compatibility with orthogonally protected and functionalized saccharide-peptide hybrids and its ability to be extended to the trisubstituted counterparts 12.

  DOI：

  10.1021/ol1003127
• 作为产物：
  描述：

  4-氰基苯硼酸 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 21.0h， 生成 4-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzonitrile
  参考文献：
  名称：

  通过优化晶体片段命中，设计一种有效的、选择性的、脑渗透性 Wnt 失活酶 Notum 抑制剂

  摘要：

  Notum 是一种羧酸酯酶，可通过 Wnt 蛋白上必需的棕榈油酸酯基团的脱酰化来抑制 Wnt 信号传导。人们越来越了解 Notum 在结直肠癌和阿尔茨海默氏病等人类疾病中所起的作用，支持发现改进的抑制剂的需要，特别是用于神经退行性疾病模型的抑制剂。在这里，我们描述了8l (ARUK3001185) 的发现和概况，它是一种有效的、选择性的、脑渗透性的 Notum 活性抑制剂，适合在啮齿动物疾病模型中口服给药。对 Diamond-SGC Poied 文库进行与 Notum 结合的晶体片段筛选，并通过生化酶测定对抑制活性进行排序，将6a和6b鉴定为一对出色的命中结果。 6的片段开发产生了8l ，在基于细胞的报告基因测定中，在 Notum 存在的情况下恢复了 Wnt 信号传导。药理学筛选评估显示8l对丝氨酸水解酶、激酶和药物靶点具有选择性。

  DOI：

  10.1021/acs.jmedchem.2c00162

文献信息

• Greener photocatalytic route to azide-alkyne cycloaddition reactions: Role of hole/oxygen in air
  作者：Subhendu Sekhar Bag、Sayantan Sinha、Siddharth Singh、Animes K. Golder

  DOI：10.1016/j.tet.2023.133703

  日期：2023.12

  for base-free click reaction in the green solvent with high efficiency, selectivity and fast reaction kinetics. Thus, the synthesized heterogeneous photocatalyst based on Cu(II) ion-doped TiO2 nanocomposite [CuII@TiO2] is found to be highly efficient for carrying out azide-alkyne 1,3-dipolar cycloaddition reaction (CuAAC) in an aqueous environment without needing a base. The reaction features high product

  我们结合了 Cu I和 Cu II的特性，代表了一种独特且智能的纳米光催化系统，可作为绿色溶剂中无碱点击反应的催化剂，具有高效率、选择性和快速反应动力学。因此，基于Cu(II)离子掺杂的TiO 2纳米复合材料合成的异相光催化剂[Cu II @TiO 2 ]被发现对于在水溶液中进行叠氮-炔1,3-偶极环加成反应(CuAAC)非常有效。环境，无需基础。该反应具有产物选择性高、反应条件温和、绿色溶剂、底物范围广、周转数优异、收率高、反应动力学快、官能团相容性好等特点。从机理上讲，在光照射（λ = 400 nm）时，TiO 2纳米核将电子从其价带释放到导带，进而光化学地将 Cu(II) 还原为 Cu(I)，从而实现对 CuAAC 反应的空间和时间控制。另一方面，空气中产生的空穴和/或氧气作为绿色氧化剂维持Cu(I)至Cu(II)催化循环。因此，产生的电子和空穴的协同作用持续维持催化循环，实现对点击
• Novel 1,2,3-Triazole Derivatives for Use against <i>Mycobacterium tuberculosis</i> H37Rv (ATCC 27294) Strain
  作者：Nubia Boechat、Vitor F. Ferreira、Sabrina B. Ferreira、Maria de Lourdes G. Ferreira、Fernando de C. da Silva、Monica M. Bastos、Marilia dos S. Costa、Maria Cristina S. Lourenço、Angelo C. Pinto、Antoniana U. Krettli、Anna Caroline Aguiar、Brunno M. Teixeira、Nathalia V. da Silva、Priscila R. C. Martins、Flavio Augusto F. M. Bezerra、Ane Louise S. Camilo、Gerson P. da Silva、Carolina C. P. Costa

  DOI：10.1021/jm2003624

  日期：2011.9.8

  The purpose of this study was to prepare various 4-substituted N-phenyl-1,2,3-triazole derivatives using click chemistry. The derivatives were screened in vitro for antimicrobial activity against Mycobacterium tuberculosis strain H37Rv (ATCC 27294) using the Alamar Blue susceptibility test. The activity was expressed as the minimum inhibitory concentration (MIC) in mu g/mL (mu M). Derivatives of isoniazid (INH), (E)-N'-[(1-aryl)-1H-1,2,3-triazole-4-yl)methylene] isonicotinoyl hydrazides, exhibited significant activity with MIC values ranging from 2.5 to 0.62 mu g/mL. In addition, they displayed low cytotoxicity against liver cells (hepatoma HepG2) and kidney cells (BGM), thereby providing a high therapeutic index. The results demonstrated the potential and importance of developing new INH derivatives to treat mycobacterial infections.
• COMPOUNDS
  申请人：UCL BUSINESS LTD

  公开号：US20210171475A1

  公开（公告）日：2021-06-10

  A compound for use in the treatment of a disease ameliorated by the inhibition of Notum of formula (I): (I)
• “Click” Synthesis of Nonsymmetrical Bis(1,2,3-triazoles)
  作者：Jesus M. Aizpurua、Itxaso Azcune、Raluca M. Fratila、Eva Balentova、Maialen Sagartzazu-Aizpurua、Jose I. Miranda

  DOI：10.1021/ol1003127

  日期：2010.4.2

  Unsymmetrically 1,1'-disubstituted 4,4'-bis-1H-1,2,3-triazoles 4 have been prepared from 4-ethynyl-1,2,3-triazoles 5 and azides. Following a "double-click" strategy, two complementary approaches were implemented for the preparation of the key 4-ethynyltriazole intermediates 5: (a) the stepwise Swern oxidation/Ohira-Bestman alkynylation of readily available 4-hydroxymethyl-1,2,3-triazoles 8 and (b) the stepwise cycloaddition of TMS-1,4-butadlyne 9. The method is highlighted by its compatibility with orthogonally protected and functionalized saccharide-peptide hybrids and its ability to be extended to the trisubstituted counterparts 12.
• Design of a Potent, Selective, and Brain-Penetrant Inhibitor of Wnt-Deactivating Enzyme Notum by Optimization of a Crystallographic Fragment Hit
  作者：Nicky J. Willis、William Mahy、James Sipthorp、Yuguang Zhao、Hannah L. Woodward、Benjamin N. Atkinson、Elliott D. Bayle、Fredrik Svensson、Sarah Frew、Fiona Jeganathan、Amy Monaghan、Stefano Benvegnù、Sarah Jolly、Luca Vecchia、Reinis R. Ruza、Svend Kjær、Steven Howell、Ambrosius P. Snijders、Magda Bictash、Patricia C. Salinas、Jean-Paul Vincent、E. Yvonne Jones、Paul Whiting、Paul V. Fish

  DOI：10.1021/acs.jmedchem.2c00162

  日期：2022.5.26

  in human diseases such as colorectal cancer and Alzheimer’s disease, supporting the need to discover improved inhibitors, especially for use in models of neurodegeneration. Here, we have described the discovery and profile of 8l (ARUK3001185) as a potent, selective, and brain-penetrant inhibitor of Notum activity suitable for oral dosing in rodent models of disease. Crystallographic fragment screening

  Notum 是一种羧酸酯酶，可通过 Wnt 蛋白上必需的棕榈油酸酯基团的脱酰化来抑制 Wnt 信号传导。人们越来越了解 Notum 在结直肠癌和阿尔茨海默氏病等人类疾病中所起的作用，支持发现改进的抑制剂的需要，特别是用于神经退行性疾病模型的抑制剂。在这里，我们描述了8l (ARUK3001185) 的发现和概况，它是一种有效的、选择性的、脑渗透性的 Notum 活性抑制剂，适合在啮齿动物疾病模型中口服给药。对 Diamond-SGC Poied 文库进行与 Notum 结合的晶体片段筛选，并通过生化酶测定对抑制活性进行排序，将6a和6b鉴定为一对出色的命中结果。 6的片段开发产生了8l ，在基于细胞的报告基因测定中，在 Notum 存在的情况下恢复了 Wnt 信号传导。药理学筛选评估显示8l对丝氨酸水解酶、激酶和药物靶点具有选择性。