5-(2-chlorophenyl)-2H-1,2,3-triazole-4-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-chlorophenyl)-2H-1,2,3-triazole-4-carboxylic acid
• 英文别名: 5-(2-chlorophenyl)-2H-triazole-4-carboxylic acid
• 化学式: C₉H₆ClN₃O₂
• 分子量: 223.619
• InChiKey: INLXWGARNHQRQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.82
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.87
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2-chlorophenyl)-2H-1,2,3-triazole-4-carboxylic acid 、 1-(3,5-二甲氧基苯基)哌嗪 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 5-(2-chlorophenyl)-4-(4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  MAY, a novel tubulin inhibitor, induces cell apoptosis in A549 and A549/Taxol cells and inhibits epithelial-mesenchymal transition in A549/Taxol cells

  摘要：

  Non-small-cell lung cancer (NSCLC) is one of the common malignant tumors, and multidrug resistance (MDR) and tumor metastasis limit the anticancer effect of NSCLC. Therefore, it is necessary to develop new anticancer drug that can inhibit MDR and metastasis of NSCLC. In the present study, we found that 5-(2-chlorophenyl)-4-(4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl)-2H-1,2,3- triazole (MAY) displayed strong cytotoxic effect on A549 and taxol-resistant A549 cells (A549/Taxol cells). We further discovered that MAY led to G2/M phase arrest by inhibiting microtubule polymerization in both cells. Then MAY caused apoptosis by the mitochondrial pathway in A549 cells and through the extrinsic pathway in A549/Taxol cells. Interestingly, MAY was not a substrate for P-glycoprotein (P-gp), which was highly expressed in A549/Taxol cells, and MAY inhibited the expression and efflux function of P-gp. Furthermore, MAY inhibited epithelial-mesenchymal transition (EMT) by targeting Twist1 in A549/Taxol cells. In summary, our results suggest that MAY induces apoptosis in A549 and A549/Taxol cells and inhibits EMT in A549/Taxol cells. These findings suggest that MAY could provide a promising method for the treatment of NSCLC, especially for the treatment of resistant NSCLC.

  DOI：

  10.1016/j.cbi.2020.109074
• 作为产物：
  描述：

  2-氯苯乙炔 在 正丁基锂 、 sodium azide 、 双氧水 、 potassium hydroxide 作用下， 以 甲醇 、 正己烷 、 二甲基亚砜 为溶剂， 反应 2.5h， 生成 5-(2-chlorophenyl)-2H-1,2,3-triazole-4-carboxylic acid
  参考文献：
  名称：

  MAY, a novel tubulin inhibitor, induces cell apoptosis in A549 and A549/Taxol cells and inhibits epithelial-mesenchymal transition in A549/Taxol cells

  摘要：

  Non-small-cell lung cancer (NSCLC) is one of the common malignant tumors, and multidrug resistance (MDR) and tumor metastasis limit the anticancer effect of NSCLC. Therefore, it is necessary to develop new anticancer drug that can inhibit MDR and metastasis of NSCLC. In the present study, we found that 5-(2-chlorophenyl)-4-(4-(3,5-dimethoxyphenyl)piperazine-1-carbonyl)-2H-1,2,3- triazole (MAY) displayed strong cytotoxic effect on A549 and taxol-resistant A549 cells (A549/Taxol cells). We further discovered that MAY led to G2/M phase arrest by inhibiting microtubule polymerization in both cells. Then MAY caused apoptosis by the mitochondrial pathway in A549 cells and through the extrinsic pathway in A549/Taxol cells. Interestingly, MAY was not a substrate for P-glycoprotein (P-gp), which was highly expressed in A549/Taxol cells, and MAY inhibited the expression and efflux function of P-gp. Furthermore, MAY inhibited epithelial-mesenchymal transition (EMT) by targeting Twist1 in A549/Taxol cells. In summary, our results suggest that MAY induces apoptosis in A549 and A549/Taxol cells and inhibits EMT in A549/Taxol cells. These findings suggest that MAY could provide a promising method for the treatment of NSCLC, especially for the treatment of resistant NSCLC.

  DOI：

  10.1016/j.cbi.2020.109074

文献信息

• NH-1,2,3-三唑-4-羧酸化合物的合成工艺
  申请人：武汉工程大学

  公开号：CN106749054A

  公开（公告）日：2017-05-31

  本发明涉及NH‑1,2,3‑三唑‑4‑羧酸化合物的新合成工艺。1)将芳基甲醛、硝基酯和叠氮化钠在催化剂的作用下，采取一锅法制得4‑酯基三唑，2)将4‑酯基三唑采用碱和酸进行水解酸化，即得到NH‑1,2,3‑三唑‑4‑羧酸化合物，本发明的有益效果是：所用实验路线为全新路线，未见报道；与已有方法相比，本文提出的方法1：产物I用其它方法很难合成；2：原料易得，价格低廉。所用原料如苯甲醛，所用催化剂如AlCl3，无机酸和碱都属于常见的化工原料，价格低廉可大量购买；3.整个路线只有两步，且都操作简便，收率较高。