N-[(2-chloro-5,7-dimethylquinolin-3-yl)methylidene]hydroxylamine | 1356485-81-8

• 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: N-[(2-chloro-5,7-dimethylquinolin-3-yl)methylidene]hydroxylamine
• CAS: 1356485-81-8
• 化学式: C₁₂H₁₁ClN₂O
• 分子量: 234.685
• InChiKey: RFFYSEPDINKBBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(2-chloro-5,7-dimethylquinolin-3-yl)methylidene]hydroxylamine 在 氯化亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 苯 为溶剂， 反应 22.5h， 生成 N-(2-((3-cyano-5,7-dimethylquinolin-2-yl)amino)ethyl)nicotinamide
  参考文献：
  名称：

  Structure–Activity Relationships of Cyanoquinolines with Corrector–Potentiator Activity in ΔF508 Cystic Fibrosis Transmembrane Conductance Regulator Protein

  摘要：

  Cystic fibrosis (CF) is caused by mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. The most common CF-causing mutation, Delta F508-CFTR, produces CFTR loss-of-function by impairing its cellular targeting to the plasma membrane and its chloride channel gating. We recently identified cyanoquinolines with both corrector ("Co", normalizing Delta F508-CFTR targeting) and potentiator ("Po", normalizing Delta F508-CFTR channel gating) activities. Here, we synthesized and characterized 24 targeted cyanoquinoline analogues to elucidate the conformational requirements for corrector and potentiator activities. Compounds with potentiator-only, corrector-only, and dual potentiator-corrector activities were found. Molecular modeling studies (conformational search double right arrow force-field lowest energy assessment double right arrow geometry optimization) suggest that (1) a flexible tether and (2) a relatively short bridge between the cyanoquinoline and arylamide moieties are important cyanoquinoline-based CoPo features. Further, these CoPo's may adopt two distinct pi-stacking conformations to elicit corrector and potentiator activities.

  DOI：

  10.1021/jm201372q
• 作为产物：
  描述：

  2-氯-5,7-二甲基-3-喹啉甲醛 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 N-[(2-chloro-5,7-dimethylquinolin-3-yl)methylidene]hydroxylamine
  参考文献：
  名称：

  Synthesis of New 3-(2-Chloroquinolin-3-yl)-5-Phenylisoxazole Derivatives via Click-Chemistry Approach

  摘要：

  Herein, we report the synthesis of new substituted 3-(2-chloroquinolin-3-yl)-5-phenylisoxazole (3a-j) by click chemistry in good to moderate yields. This approach is based on the regioselective copper(I)-catalyzed cycloaddition between different nitrile oxides derived from 2-chloroquinoline-3- carbaldehyde (2a-j) and phenylacetylene. Finally these derivatives were screened for their antibacterial evaluation in vitro against three Gram-negative clinical bacteria: Escherichia coli, Pseudomonas aeruginosa and Acinetobacter baumannii using standard methods.

  DOI：

  10.5935/0103-5053.20140002