N-(3-(三氟甲基)苯基)琥珀酰亚胺 | 15386-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: N-(3-(三氟甲基)苯基)琥珀酰亚胺
• 英文名称: 1-(3-Trifluormethyl-phenyl)-2,5-dioxo-pyrrolidin
• 英文别名: 1-[3-(Trifluoromethyl)phenyl]pyrrolidine-2,5-dione
• CAS: 15386-94-4
• 化学式: C₁₁H₈F₃NO₂
• 分子量: 243.185
• InChiKey: GQCQERWJFWBERU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-(三氟甲基)苯基)琥珀酰亚胺 、 2-苯基咪唑并[1,2-a]吡啶 在 五羰基溴化锰(I) 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以59%的产率得到3-(2-(imidazo[1,2-a]pyridin-2-yl)phenyl)-1-(3-(trifluoromethyl)phenyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Solvent-Switched Manganese(I)-Catalyzed Regiodivergent Distal vs Proximal C–H Alkylation of Imidazopyridine with Maleimide

  摘要：

  DOI：

  10.1021/acs.orglett.1c02536
• 作为产物：
  描述：

  3-(trifluoromethyl)phenyllithium 在 硼酸三甲酯 、 copper diacetate 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(3-(三氟甲基)苯基)琥珀酰亚胺
  参考文献：
  名称：

  Cupric acetate mediated N-arylation by arylboronic acids: A preliminary investigation into the scope of application

  摘要：

  A range of NH substrates of varying nucleophilicity were reacted with a selection of electronically diverse aryl boronic acids in the presence of cupric acetate in order to evaluate the generality of a previously described N-arylation procedure. The results of that investigation are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01735-3

文献信息

• Thiazolidinone CFTR inhibitors with improved water solubility identified by structure–activity analysis
  作者：N.D. Sonawane、A.S. Verkman

  DOI：10.1016/j.bmc.2008.07.044

  日期：2008.9

  The thiazolidinone 3-[(3-trifluoromethyl)phenyl]-5-[(4-carboxyphenyl)methylene]-2-thioxo-4-thiazolidinone (CFTRinh-172) inhibits cystic fibrosis transmembrane conductance regulator ( CFTR) chloride channel conductance with submicromolar affinity and blocks cholera toxin-induced intestinal fluid secretion. Fifty-eight CFTRinh-172 analogs were synthesized to identify CFTR inhibitors with improved water solubility, exploring modi. cations in its two phenyl rings, thiazolidinone core, and core-phenyl connectors. Greatest CFTR inhibition potency was found for 3-CF3 and polar group-substituted-phenyl rings, and a thiazolidinone core. Two compounds with similar to 1 mu M CFTR inhibition potency and solubility >180 mu M(>10-fold more than CFTRinh-172) were identified: Tetrazolo-172, containing 4-tetrazolophenyl in place of 4-carboxyphenyl, and Oxo-172, containing thiazolidinedione in place of the thiazolidinone core. These water soluble thiazolidinone analogs had low cellular toxicity. The improved water solubility of Tetrazolo- and Oxo-172 make them potential lead candidates for therapy of secretory diarrheas and polycystic kidney disease. (C) 2008 Elsevier Ltd. All rights reserved.