1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbaldehyde | 1622136-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbaldehyde
• 英文别名: 1-(7-Chloro-4-quinolyl)triazole-4-carbaldehyde；1-(7-chloroquinolin-4-yl)triazole-4-carbaldehyde
• CAS: 1622136-85-9
• 化学式: C₁₂H₇ClN₄O
• 分子量: 258.667
• InChiKey: HKPAMLSSTJWQHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbaldehyde 在 二甲氨基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到7-chloro-4-(4-(difluoromethyl)-1H-1,2,3-triazol-1-yl)quinoline
  参考文献：
  名称：

  New Compounds Hybrids 1 H ‐1,2,3‐Triazole‐Quinoline Against Plasmodium falciparum

  摘要：

  Malaria is one of the most prevalent parasitic diseases in the world. The global importance of this disease, current vector control limitations, and the absence of an effective vaccine make the use of therapeutic antimalarial drugs the main strategy to control malaria. Chloroquine is a cost‐effective antimalarial drug with a relatively robust safety profile, or therapeutic index. However, chloroquine is no longer used alone to treat patients with Plasmodium falciparum due to the emergence and spread of chloroquine‐resistant strains, which have also been reported for Plasmodium vivax. However, the activity of 1,2,3‐triazole derivatives against chloroquine‐sensitive and chloroquine‐resistant strains of P. falciparum has been reported in the literature. To enhance the anti‐P. falciparum activity of quinoline derivatives, we synthesized 11 new quinoline‐1H‐1,2,3‐triazole hybrids with different substituents in the 4‐positions of the 1H‐1,2,3‐triazole ring, which were assayed against the W2‐chloroquine‐resistant P. falciparum clone. Six compounds exhibited activity against the P. falciparum W2 clone, chloroquine‐resistant, with IC50 values ranging from 1.4 to 46 μm. None of these compounds was toxic to a normal monkey kidney cell line, thus exhibiting good selectivity indexes, as high 351 for one compound (11).

  DOI：

  10.1111/cbdd.12321
• 作为产物：
  描述：

  4-叠氮基-7-氯喹啉 在 copper(ll) sulfate pentahydrate 、 草酰氯 、 二甲基亚砜 、 sodium ascorbate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 26.25h， 生成 1-(7-chloroquinolin-4-yl)-1H-1,2,3-triazole-4-carbaldehyde
  参考文献：
  名称：

  New Compounds Hybrids 1 H ‐1,2,3‐Triazole‐Quinoline Against Plasmodium falciparum

  摘要：

  Malaria is one of the most prevalent parasitic diseases in the world. The global importance of this disease, current vector control limitations, and the absence of an effective vaccine make the use of therapeutic antimalarial drugs the main strategy to control malaria. Chloroquine is a cost‐effective antimalarial drug with a relatively robust safety profile, or therapeutic index. However, chloroquine is no longer used alone to treat patients with Plasmodium falciparum due to the emergence and spread of chloroquine‐resistant strains, which have also been reported for Plasmodium vivax. However, the activity of 1,2,3‐triazole derivatives against chloroquine‐sensitive and chloroquine‐resistant strains of P. falciparum has been reported in the literature. To enhance the anti‐P. falciparum activity of quinoline derivatives, we synthesized 11 new quinoline‐1H‐1,2,3‐triazole hybrids with different substituents in the 4‐positions of the 1H‐1,2,3‐triazole ring, which were assayed against the W2‐chloroquine‐resistant P. falciparum clone. Six compounds exhibited activity against the P. falciparum W2 clone, chloroquine‐resistant, with IC50 values ranging from 1.4 to 46 μm. None of these compounds was toxic to a normal monkey kidney cell line, thus exhibiting good selectivity indexes, as high 351 for one compound (11).

  DOI：

  10.1111/cbdd.12321