2-(4-cyanobenzylidene)-1-(6-methyl-2H-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazine | 1392812-74-6

• 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: 2-(4-cyanobenzylidene)-1-(6-methyl-2H-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazine
• 英文别名: 4-[[(6-methyl-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazinylidene]methyl]benzonitrile
• CAS: 1392812-74-6
• 化学式: C₁₉H₁₄N₄O₂
• 分子量: 330.346
• InChiKey: DJDCTOROFNWCQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-cyanobenzylidene)-1-(6-methyl-2H-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazine 在 盐酸羟胺 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以39%的产率得到(Z)-N'-hydroxy-4-((E)-(2-(6-methyl-2H-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazono)methyl)benzimidamide
  参考文献：
  名称：

  Quinolylhydrazones as novel inhibitors of Plasmodium falciparum serine protease PfSUB1

  摘要：

  Plasmodium falciparum subtilisin-like protease 1 (PfSUB1) is a serine protease that plays key roles in the egress of the parasite from red blood cells and in preparing the released merozoites for the subsequent invasion of new erythrocytes. The development of potent and selective PfSUB1 inhibitors could pave the way to the discovery of potential antimalarial drugs endowed with an innovative mode of action and consequently able to overcome the current problems of resistance to established chemotherapies. Through the screening of a proprietary library of compounds against PfSUB1, we identified hydrazone 2 as a hit compound. Here we report a preliminary investigation of the structure-activity relationships for a class of PfSUB1 inhibitors related to our identified hit. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.023
• 作为产物：
  描述：

  4-氰基苯甲醛 、 6-metil-8-idrazino-1,3-diossol<4,5-g>chinolina 以 乙醇 为溶剂， 反应 14.0h， 生成 2-(4-cyanobenzylidene)-1-(6-methyl-2H-[1,3]dioxolo[4,5-g]quinolin-8-yl)hydrazine
  参考文献：
  名称：

  Quinolylhydrazones as novel inhibitors of Plasmodium falciparum serine protease PfSUB1

  摘要：

  Plasmodium falciparum subtilisin-like protease 1 (PfSUB1) is a serine protease that plays key roles in the egress of the parasite from red blood cells and in preparing the released merozoites for the subsequent invasion of new erythrocytes. The development of potent and selective PfSUB1 inhibitors could pave the way to the discovery of potential antimalarial drugs endowed with an innovative mode of action and consequently able to overcome the current problems of resistance to established chemotherapies. Through the screening of a proprietary library of compounds against PfSUB1, we identified hydrazone 2 as a hit compound. Here we report a preliminary investigation of the structure-activity relationships for a class of PfSUB1 inhibitors related to our identified hit. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.023