(S)-1-(quinolin-8-ylsulfonyl)pyrrolidine-2-carboxylic acid | 87650-63-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-1-(quinolin-8-ylsulfonyl)pyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-quinolin-8-ylsulfonylpyrrolidine-2-carboxylic acid
• CAS: 87650-63-3
• 化学式: C₁₄H₁₄N₂O₄S
• mdl: MFCD05148208
• 分子量: 306.342
• InChiKey: AFQOHCPIHVZWGB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-乙基苯胺 、 (S)-1-(quinolin-8-ylsulfonyl)pyrrolidine-2-carboxylic acid 在 N,N-二异丙基乙胺 、 O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以0.053 g的产率得到(S)-N-(2-ethylphenyl)-1-(quinolin-8-ylsulfonyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  (S)-N-(2,5-Dimethylphenyl)-1-(quinoline-8-ylsulfonyl)pyrrolidine-2-carboxamide as a Small Molecule Inhibitor Probe for the Study of Respiratory Syncytial Virus Infection

  摘要：

  A high-throughput, cell-based screen was used to identify chemotypes as inhibitors for human respiratory syncytial virus (hRSV). Optimization of a sulfonylpyrrolidine scaffold resulted in compound 50 that inhibited a virus-induced cytopathic effect in the entry stage of infection (EC50 = 2.3 +/- 0.8 mu M) with marginal cytotoxicity (CC50 = 30.9 +/- 1.1 mu M) and reduced viral titer by 100-fold. Compared to ribavirin, sulfonylpyrrolidine 50 demonstrated an improved in vitro potency and selectivity index.

  DOI：

  10.1021/jm300612z
• 作为产物：
  描述：

  喹啉-8-磺酰氯 、 D-脯氨酸 在 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以60%的产率得到(S)-1-(quinolin-8-ylsulfonyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  (S)-N-(2,5-Dimethylphenyl)-1-(quinoline-8-ylsulfonyl)pyrrolidine-2-carboxamide as a Small Molecule Inhibitor Probe for the Study of Respiratory Syncytial Virus Infection

  摘要：

  A high-throughput, cell-based screen was used to identify chemotypes as inhibitors for human respiratory syncytial virus (hRSV). Optimization of a sulfonylpyrrolidine scaffold resulted in compound 50 that inhibited a virus-induced cytopathic effect in the entry stage of infection (EC50 = 2.3 +/- 0.8 mu M) with marginal cytotoxicity (CC50 = 30.9 +/- 1.1 mu M) and reduced viral titer by 100-fold. Compared to ribavirin, sulfonylpyrrolidine 50 demonstrated an improved in vitro potency and selectivity index.

  DOI：

  10.1021/jm300612z

文献信息

• (<i>S</i>)-<i>N</i>-(2,5-Dimethylphenyl)-1-(quinoline-8-ylsulfonyl)pyrrolidine-2-carboxamide as a Small Molecule Inhibitor Probe for the Study of Respiratory Syncytial Virus Infection
  作者：Blake P. Moore、Dong Hoon Chung、Daljit S. Matharu、Jennifer E. Golden、Clinton Maddox、Lynn Rasmussen、James W. Noah、Melinda I. Sosa、Subramaniam Ananthan、Nichole, A. Tower、E. Lucile White、Fuli Jia、Thomas E. Prisinzano、Jeffrey Aubé、Colleen B. Jonsson、William E. Severson

  DOI：10.1021/jm300612z

  日期：2012.10.25

  A high-throughput, cell-based screen was used to identify chemotypes as inhibitors for human respiratory syncytial virus (hRSV). Optimization of a sulfonylpyrrolidine scaffold resulted in compound 50 that inhibited a virus-induced cytopathic effect in the entry stage of infection (EC50 = 2.3 +/- 0.8 mu M) with marginal cytotoxicity (CC50 = 30.9 +/- 1.1 mu M) and reduced viral titer by 100-fold. Compared to ribavirin, sulfonylpyrrolidine 50 demonstrated an improved in vitro potency and selectivity index.