[1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]methanamine | 1251123-30-4

• 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-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]methanamine
• 英文别名: [1-(4-methoxyphenyl)triazol-4-yl]methanamine
• CAS: 1251123-30-4
• 化学式: C₁₀H₁₂N₄O
• mdl: MFCD16666620
• 分子量: 204.231
• InChiKey: IETJARHMOAUKNP-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(4-methoxyphenyl)-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-(((1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)amino)-2-oxoethyl(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：

  甲氧苯胺 在 盐酸 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 19.5h， 生成 [1-(4-methoxyphenyl)-1H-1,2,3-triazol-4-yl]methanamine
  参考文献：
  名称：

  Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway

  摘要：

  A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 mu M) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 mu M) and 5-Fu (IC50 = 24.80 mu M) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.04.005

文献信息

• 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。
• ‘Click’ assembly of selective inhibitors for MAO-A
  作者：Zhao Jia、Qing Zhu

  DOI：10.1016/j.bmcl.2010.08.104

  日期：2010.11

  In this Letter, an efficient strategy for the fast construction of 108 compounds library was developed using click chemistry. The fingerprint of inhibitory activity toward MAO-A/B against this library was obtained, and four hit compounds were identified as selective inhibitors toward MAO-A. Docking study was carried out to demonstrate the binding mode between a9 and MAO-A/B, and the result reveals that a9 localized in the 'aromatic cage' and oriented to establish pi-pi stacking interactions with Tyr407, Tyr444 and FAD in MAO-A rather than in MAO-B. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of (+)-Usnic Acid Derivatives as Potential Anti-<i>Toxoplasma gondii</i> Agents
  作者：Hong-Yan Guo、ChunMei Jin、Hai-Ming Zhang、Chun-Mei Jin、Qing-Kun Shen、Zhe-Shan Quan

  DOI：10.1021/acs.jafc.9b02173

  日期：2019.8.28

  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.