(1-phenyl-1H-1,2,3-triazol-4-yl)methanamine

• 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-phenyl-1H-1,2,3-triazol-4-yl)methanamine
• 英文别名: (1-phenyltriazol-4-yl)methanamine
• 化学式: C₉H₁₀N₄
• mdl: MFCD08056628
• 分子量: 174.205
• InChiKey: LHCAALSSPCHRFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 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-phenyl-1H-1,2,3-triazol-4-yl)methanamine 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-oxo-2-(((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)amino)ethyl(2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylate
  参考文献：
  名称：

  Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113474
• 作为产物：
  描述：

  苯胺 在 盐酸 、 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (1-phenyl-1H-1,2,3-triazol-4-yl)methanamine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of (+)-Usnic Acid Derivatives as Potential Anti-Toxoplasma gondii Agents

  摘要：

  Six series of (+)-usnic acid derivatives were synthesized. The IC50 values of these compounds were determined in T. gondii infected HeLa cells (mu M) and in HeLa cells (mu M), and their selectivity indexes (SI) were calculated. In vitro, most of the derivatives tested in this study exhibited more anti activity than that of the parent compound (+)-usnic acid and the positive control drugs. Among these derivatives, methyl (E)-(1-(6-acetyl-7,9-dihydroxy-8,9b-dimethyl-1,3-dioxo-3,9b-dihydrodibenzo[b,d]furan-2(1H)-ylidene)ethyl)phenylalaninate (D3) showed the most effective anti-T. gondii activity (selectivity >2.77). In comparison with the clinically used positive control drugs sulfadiazine (selectivity 1.15), pyrimethamine (selectivity 0.89), spiramycin (selectivity 0.72), and the lead compound (+)-usnic acid (selectivity 0.96), D3 showed better results in vitro. Furthermore, D3 and (E)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-2-(1-(quinolin-6-ylamino)ethylidene)dibenzo[b,d]furan-1,3-(2H,9bH)-dione (F3) had greater inhibitory effects on T. gondii (inhibition rates 76.0% and 64.6%) in vivo in comparison to spiramycin (inhibition rate 55.2%); in the peritoneal cavity of mice, the number of tachyzoites was significantly reduced (p < 0.001) in vivo. Additionally, some biochemical parameters were measured and spleen indexes were comprehensively evaluated, and the results indicated that mice treated with both compound D3 and compound F3 showed reduced hepatotoxicity and significantly enhanced antioxidative effects in comparison to the normal group. Granuloma and cyst formation were effected by the inhibition of compound D3 and compound F3 in liver sections. Overall, these results indicated that D3 and F3 for use as anti-T. gondii agents are promising lead compounds.

  DOI：

  10.1021/acs.jafc.9b02173

文献信息

• Copper-γ-cyclodextrin complexes immobilized on hexagonal boron nitride as an efficient catalyst in the multicomponent synthesis of 1,2,3-triazoles
  作者：Ruifang Nie、Rui Sang、Xiaojun Ma、Yang Zheng、Xu Cheng、Weijian Li、Li Guo、Hui Jin、Yong Wu

  DOI：10.1016/j.jcat.2016.09.022

  日期：2016.12

  recoverable and reusable heterogeneous catalyst can be used in the click synthesis of 1,2,3-triazoles via a one-pot three-component reaction of boracic acid, terminal alkynes, and sodium azide at room temperature in water. FT-IR, XRD, SEM, XPS, TG, and ICP-AES techniques were used to characterize the catalyst. In general, this reaction, with the aid of this new catalyst, afforded the corresponding products

  首次制备了固定在六方氮化硼上的铜-γ-环糊精配合物（h [受电子邮件保护]γ[受电子邮件保护]（OAc）2）。这种可回收和可重复使用的非均相催化剂可在室温下于水中通过硼酸，末端炔烃和叠氮化钠的一锅式三组分反应用于1,2,3-三唑的点击合成。FT-IR，XRD，SEM，XPS，TG和ICP-AES技术用于表征催化剂。通常，在这种新型催化剂的帮助下，该反应得到具有良好产率和对官能团的优异耐受性的相应产物。
• [EN] O-ALKYL TRIAZOLYL CARBAMATES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE (FAAH)<br/>[FR] CARBAMATES DE O-ALKYLTRIAZOLYLE EN TANT QU'INHIBITEURS DE L'HYDROLASE DES AMIDES D'ACIDES GRAS (FAAH)
  申请人：FOND ISTITUTO ITALIANO DI TECNOLOGIA

  公开号：WO2015007613A1

  公开（公告）日：2015-01-22

  The present invention provides compounds of formula I and pharmaceutical compositions for inhibiting fatty acid amide hydrolase (FAAH). Inhibition of FAAH is contemplated as a method to sustain the levels of the fatty acid ethanolamides arachidonoylethanolamide (AEA), palmitoylethanolamide (PEA), and oleoylethanolamide (OEA), three substrates of FAAH, in conditions characterized byreduced concentrations of AEA, PEA and OEA. The invention also provides methods for treating disorders in which decreased levels of AEA, PEA and OEA are associated with the disorder.

  本发明提供了式I的化合物和用于抑制脂肪酸酰胺水解酶（FAAH）的药物组合物。考虑到通过抑制FAAH来维持脂肪酸乙醇胺花生四烯酰胺（AEA）、棕榈酰胺乙醇胺（PEA）和油酰胺乙醇胺（OEA）这三种FAAH底物的水平的方法，适用于在其特征为AEA、PEA和OEA浓度降低的情况下。本发明还提供了治疗与降低的AEA、PEA和OEA水平相关的疾病的方法。
• Synthesis and biological evaluation of ursolic acid derivatives bearing triazole moieties as potential anti-<i>Toxoplasma gondii</i> agents
  作者：Tian Luan、Chunmei Jin、Chun-Mei Jin、Guo-Hua Gong、Zhe-Shan Quan

  DOI：10.1080/14756366.2019.1584622

  日期：2019.1.1

  Ursolic acid (UA), a plant-derived compound, has many properties beneficial to health. In the present study, we synthesised three series of novel UA derivatives and evaluated their anti-Toxoplasma gondii activity both in vitro and in vivo. Most derivatives exhibited an improved anti-T. gondii activity in vitro when compared with UA (parent compound), whereas compound 3d exhibited the most potent anti-T

  抽象的 乌索酸（UAS），一种植物来源的化合物，具有许多有益于健康的特性。在本研究中，我们合成了三个系列的新型UA衍生物，并在体外和体内评估了它们的抗弓形虫活性。与UA（母体化合物）相比，大多数衍生物在体外均表现出改善的抗弓形虫活性，而化合物3d在体内表现出最有效的抗弓形虫活性。螺旋霉素为阳性对照。此外，与UA相比，确定包括肝脏和脾脏指标在内的生化指标表明化合物3d可有效降低肝毒性并显着增强抗氧化作用。此外，我们的分子对接研究表明化合物3d对弓形虫钙依赖性蛋白激酶1（TgCDPK1）具有很强的结合亲和力。根据这些发现，我们得出结论，UA的衍生物3d可作为TgCDPK1的潜在抑制剂。
• Design and Synthesis of C-19 Isosteviol Derivatives as Potent and Highly Selective Antiproliferative Agents
  作者：Tian Luan、Li-Hua Cao、Hao Deng、Qing-Kun Shen、Yu-Shun Tian、Zhe-Shan Quan

  DOI：10.3390/molecules24010121

  日期：——

  and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. Most of the derivatives tested here exhibited improved antiproliferative activity with high selectivity when compared with the parent compound isosteviol and the positive control drug 5-fluorouracil. Among these derivatives; compound 5d exhibited

  六大系列新型异甜菊醇衍生物；在 C-19 位置修改；被合成；并在体外评估了它们对三种人类癌细胞系（HCT-116；BEL-7402；HepG2）和人类 L02 正常细胞系的抗增殖活性。与母体化合物异甜菊醇和阳性对照药物 5-氟尿嘧啶相比，这里测试的大多数衍生物表现出更高的抗增殖活性和高选择性。在这些衍生物中；化合物 5d 在癌细胞和正常细胞之间表现出最有效的抗增殖活性和值得称赞的选择性。此外; 化合物5d以浓度依赖性方式抑制HCT-116细胞的集落形成。进一步的研究表明，化合物5d在S期阻滞了HCT-116细胞周期；蛋白质印迹分析表明该机制可能与细胞周期蛋白 A 表达的变化有关；细胞周期蛋白 B1; 和细胞周期蛋白 E1。此外; 一项涉及将化合物 5d 置于 CDK2/细胞周期蛋白 A 结合位点的对接研究结果表明，其作用方式可能是一种 CDK2/细胞周期蛋白 A 抑制剂。
• Cu/Cu-oxide nanoparticles as catalyst in the “click” azide–alkyne cycloaddition
  作者：Giorgio Molteni、Claudia L. Bianchi、Giorgio Marinoni、Nadia Santo、Alessandro Ponti

  DOI：10.1039/b604297j

  日期：——

  Mixed Cu/Cu-oxide nanoparticles are an effective catalyst for the “click” 1,3-dipolar cycloaddition between azides and terminal alkynes, featuring short reaction times, soft reaction conditions and full regioselectivity.

  混合铜/氧化铜纳米粒子是叠氮化物与端炔类化合物进行 "click "1,3-二极环加成反应的有效催化剂，具有反应时间短、反应条件温和以及完全区域选择性等特点。