1-(p-aminobenzyl)-4-phenyl-1H-1,2,3-triazole | 104951-48-6

• 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-(p-aminobenzyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 4-((4-phenyl-1H-1,2,3-triazole-1-yl)methyl)aniline；4-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)aniline；4-((4-Phenyl-1h-1,2,3-triazole-1-yl)methyl) aniline；4-[(4-phenyltriazol-1-yl)methyl]aniline
• CAS: 104951-48-6
• 化学式: C₁₅H₁₄N₄
• 分子量: 250.303
• InChiKey: PGMVSMMPBUATSE-UHFFFAOYSA-N

物化性质

• 沸点：
  502.0±52.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(p-aminobenzyl)-4-phenyl-1H-1,2,3-triazole 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 盐酸羟胺 、 乙酸酐 、 溶剂黄146 、 sodium sulfate 作用下， 以 水 为溶剂， 反应 3.0h， 生成 6-[(4-phenyltriazol-1-yl)methyl]-1H-3,1-benzoxazine-2,4-dione
  参考文献：
  名称：

  Discovery of Tryptanthrin Derivatives as Potent Inhibitors of Indoleamine 2,3-Dioxygenase with Therapeutic Activity in Lewis Lung Cancer (LLC) Tumor-Bearing Mice

  摘要：

  Indoleamine 2,3-dioxygenase (IDO-1) is emerging as an important new therapeutic target for the treatment of cancer, neurological disorders, and other diseases that are characterized by pathological tryptophan metabolism. However, only a few structural classes are known to be IDO-1 inhibitors. In this study, a natural compound tryptanthrin was discovered to be a novel potent IDO-1 inhibitor by screening of indole-based structures. Three series of 13 tryptanthrin derivatives were synthesized, and the structure-activity analysis was undertaken. The optimization led to the identification of 5c, which exhibited the inhibitory activity at a nanomolar level. In vitro 5c dramatically augmented the proliferation of T cells. When administered to Lewis lung cancer (LLC) tumor-bearing mice, 5c significantly inhibited IDO-1 activity and suppressed tumor growth. In addition, 5c reduced the numbers of Fox3(+) regulatory T cells (Tregs), which are known to prevent the development of efficient antitumor immune responses.

  DOI：

  10.1021/jm401195n
• 作为产物：
  描述：

  4-苯基-1,2,3-三氮唑 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 24.0h， 生成 1-(p-aminobenzyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Biagi; Livi; Scartoni, Farmaco, Edizione Scientifica, 1986, vol. 41, # 8, p. 597 - 610

  摘要：

  DOI：

文献信息

• Synergistic Effects of ppm Levels of Palladium on Natural Clinochlore for Reduction of Nitroarenes
  作者：Mohammad Gholinejad、Erfan Oftadeh、Mohammad Shojafar、José M. Sansano、Bruce H. Lipshutz

  DOI：10.1002/cssc.201901535

  日期：2019.9.20

  occurring clay clinochlore with ppm amounts of palladium leads to a new and very effective reagent for the reduction of numerous aromatic nitro species. When palladium nanoparticles are supported on pyridyltriazole-modified clinochlore, iron within clinochlore acts synergistically with palladium to catalyze the reduction of a wide variety of nitroarenes at room temperature in aqueous media. Based on

  用ppm量的钯增强改性的天然存在的粘土斜绿石，会导致一种新型的，非常有效的还原大量芳香硝基物种的试剂。当钯纳米颗粒负载在吡啶基三唑改性的氯丁酸上时，氯丁二酸中的铁与钯协同作用，在室温下在水性介质中催化多种硝基芳烃的还原。根据电子因子的计算，发现该催化剂体系符合绿色化学标准，可以循环使用多达五次。
• APPLICATION OF N-BENZYL TRYPTANTHRIN DERIVATIVE AS TRYPTOPHAN DIOXYGENASE (TDO) INHIBITOR
  申请人：FUDAN UNIVERSITY

  公开号：US20200101075A1

  公开（公告）日：2020-04-02

  The present invention provides an application of N-benzyl tryptanthrin derivative as tryptophan dioxygenase (TDO) inhibitor, and more specifically an application of N-benzyl tryptanthrin derivative or a pharmaceutically acceptable salt thereof. Said derivative has a structural general formula as represented by formula 1, wherein each group is defined as in the specification. The derivative of the present invention has a good TDO inhibiting activity and can be used to prepare a treatment for diseases associated with TDO activity and expression.

  本发明提供了N-苄基色胺酸三氮杂吲哚衍生物作为色氨酸双氧酶(TDO)抑制剂的应用，更具体地是N-苄基色胺酸三氮杂吲哚衍生物或其药用可接受的盐的应用。所述衍生物具有由式1表示的结构通用公式，其中每个基团如规范中所定义。本发明的衍生物具有良好的TDO抑制活性，可用于制备与TDO活性和表达相关的疾病的治疗。
• Design, synthesis, and biological evaluation of some 1,2,3-triazole derivatives as novel amide-based inhibitors of soluble epoxide hydrolase
  作者：Elham Rezaee、Hamid Reza Shadzad、Maryam Nazari、Sayyed Abbas Tabatabai

  DOI：10.1007/s00044-021-02752-3

  日期：2021.9

  pharmacological agents have been developed to inhibit the soluble epoxide hydrolase (sEH) and consequently, maintain EETs serum level in high concentrations. In the present study, a series of novel amide derivatives were designed and investigated with a 1,2,3-triazole ring as a secondary pharmacophore against sEH enzyme. Based on docking studies, these novel structures were suitably located in the active

  环氧二十碳三烯酸 (EET) 是由细胞色素 P 450 (CYP) 对花生四烯酸 (AA) 的作用产生的，对肾脏和心血管系统具有有益的作用。近几十年来，已经开发出许多新的药物来抑制可溶性环氧化物水解酶 (sEH)，从而将 EET 的血清水平维持在高浓度。在本研究中，设计并研究了一系列新型酰胺衍生物，其中 1,2,3-三唑环作为抗 sEH 酶的二级药效团。基于对接研究，这些新结构适当地位于酶的活性位点。所有最终化合物均显示出令人满意的 sEH 抑制活性，具有适当的 IC 50值 (0.9–55.5 nM)。化合物5l，作为最有效的化合物，可能是进一步研究的有价值的结构。根据计算机 ADME 计算，这些新化合物可以配制成口服活性剂。
• Introducing Savie: A Biodegradable Surfactant Enabling Chemo- and Biocatalysis and Related Reactions in Recyclable Water
  作者：Joseph R. A. Kincaid、Madison J. Wong、Nnamdi Akporji、Fabrice Gallou、David M. Fialho、Bruce H. Lipshutz

  DOI：10.1021/jacs.2c13444

  日期：——

  organic synthesis in recyclable water. This includes homogeneous catalysis (including examples employing only ppm levels of catalyst), heterogeneous catalysis, and biocatalytic transformations, including a multistep chemoenzymatic sequence. Use of Savie frequently leads to significantly higher yields than do conventional surfactants, while obviating the need for waste-generating organic solvents.

  Savie 是一种可生物降解的表面活性剂，源自维生素 E 和聚肌氨酸 (PSar)，开发用于可循环水中的有机合成。这包括均相催化（包括仅使用 ppm 级催化剂的例子）、多相催化和生物催化转化，包括多步化学酶序列。使用 Savie 通常会比传统表面活性剂产生显着更高的产率，同时无需使用产生废物的有机溶剂。
• Discovery of Tryptanthrin Derivatives as Potent Inhibitors of Indoleamine 2,3-Dioxygenase with Therapeutic Activity in Lewis Lung Cancer (LLC) Tumor-Bearing Mice
  作者：Shuangshuang Yang、Xishuai Li、Fangfang Hu、Yinlong Li、Yunyun Yang、Junkai Yan、Chunxiang Kuang、Qing Yang

  DOI：10.1021/jm401195n

  日期：2013.11.14

  Indoleamine 2,3-dioxygenase (IDO-1) is emerging as an important new therapeutic target for the treatment of cancer, neurological disorders, and other diseases that are characterized by pathological tryptophan metabolism. However, only a few structural classes are known to be IDO-1 inhibitors. In this study, a natural compound tryptanthrin was discovered to be a novel potent IDO-1 inhibitor by screening of indole-based structures. Three series of 13 tryptanthrin derivatives were synthesized, and the structure-activity analysis was undertaken. The optimization led to the identification of 5c, which exhibited the inhibitory activity at a nanomolar level. In vitro 5c dramatically augmented the proliferation of T cells. When administered to Lewis lung cancer (LLC) tumor-bearing mice, 5c significantly inhibited IDO-1 activity and suppressed tumor growth. In addition, 5c reduced the numbers of Fox3(+) regulatory T cells (Tregs), which are known to prevent the development of efficient antitumor immune responses.