(2S)-N-(2-nitrophenyl)pyrrolidine-2-carboxamide | 403478-64-8

• 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: (2S)-N-(2-nitrophenyl)pyrrolidine-2-carboxamide
• CAS: 403478-64-8
• 化学式: C₁₁H₁₃N₃O₃
• mdl: MFCD13246145
• 分子量: 235.243
• InChiKey: SRCLPEYQCODXDE-VIFPVBQESA-N

物化性质

• 沸点：
  470.9±40.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-N-(2-nitrophenyl)pyrrolidine-2-carboxamide 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S)-1-[(2S)-2-amino-4-methylsulfanylbutanoyl]-N-(2-nitrophenyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Discovery and SAR studies of methionine–proline anilides as dengue virus NS2B-NS3 protease inhibitors

  摘要：

  A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with K-i values of 4.9 and 10.5 mu M. The structure and activity relationship and the molecular docking revealed that L-proline, L-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.071
• 作为产物：
  描述：

  BOC-L-脯氨酸 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S)-N-(2-nitrophenyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Discovery and SAR studies of methionine–proline anilides as dengue virus NS2B-NS3 protease inhibitors

  摘要：

  A series of methionine-proline dipeptide derivatives and their analogues were designed, synthesized and assayed against the serotype 2 dengue virus NS2B-NS3 protease, and methionine-proline anilides 1 and 2 were found to be the most active DENV 2 NS2B-NS3 competitive inhibitors with K-i values of 4.9 and 10.5 mu M. The structure and activity relationship and the molecular docking revealed that L-proline, L-methionine and p-nitroaniline in 1 and 2 are the important characters in blocking the active site of NS2B-NS3 protease. Our current results suggest that the title dipeptidic scaffold represents a promising structural core to discover a new class of active NS2B-NS3 competitive inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.071

文献信息

• Discovery and structure–activity relationships of urea derivatives as potent and novel CCR3 antagonists
  作者：Aiko Nitta、Yosuke Iura、Hiroki Tomioka、Ippei Sato、Koichiro Morihira、Hirokazu Kubota、Tatsuaki Morokata、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto、Takayuki Imaoka、Toshiya Takahashi

  DOI：10.1016/j.bmcl.2012.06.042

  日期：2012.8

  The synthesis and structure-activity relationships of ureas as CCR3 antagonists are described. Optimization starting with lead compound 2 (IC50 = 190 nM) derived from initial screening hit compound 1 (IC50 = 600 nM) led to the identification of (S)-N-((1R,3S,5S)-8-((6-fluoronaphthalen-2-yl)methyl)-8-azabicyclo[3.2.1]octan-3-yl)-N-(2-nitrophenyl)pyrrolidine-1,2-dicarboxamide 27 (IC50 = 4.9 nM) as a potent CCR3 antagonist. (c) 2012 Elsevier Ltd. All rights reserved.