(2S,4S)-1-(tert-butoxycarbonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylic acid

• 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,4S)-1-(tert-butoxycarbonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylic acid
• 英文别名: (2S,4S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-(4-phenyltriazol-1-yl)pyrrolidine-2-carboxylic acid
• 化学式: C₁₈H₂₂N₄O₄
• 分子量: 358.397
• InChiKey: ADNVHPPFKNQHHE-ZFWWWQNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-1-(tert-butoxycarbonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylic acid 在 N-甲基吗啉 、 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 benzyl ((S)-1-cyclohexyl-2-((2S,4S)-2-(((R)-1-(cyclopropanesulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamoyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)-2-oxoethyl)carbamate
  参考文献：
  名称：

  Discovery of a series of novel compounds with moderate anti-hepatitis C virus NS3 protease activity in vitro

  摘要：

  The hepatitis C virus (HCV) NS3/4A protease that plays an important role in the viral life cycle has been proven to be an excellent target for the discovery of anti-HCV drugs. Enlightened by some P2-triazole and amide compounds, which had been found as HCV NS3 protease inhibitors, we designed and synthesized a series of novel compounds by incorporating different amino acid residues in P1/P1' and P3/P3' position to develop novel antiviral agents. The result of enzyme inhibition assay indicated that all the designed compounds showed moderate anti-HCV NS3 protease activity. On the basis of the biological result, a detailed structure-activity relationship (SAR) was derived and discussed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.032
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-cis-4-(4-phenyl-1H-1,2,3-triazol-1-yl)-L-proline methyl ester 在 lithium hydroxide monohydrate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 (2S,4S)-1-(tert-butoxycarbonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  通过硫酰基自由基催化介导对映选择性环加成的二硫键桥接肽

  摘要：

  描述了对映选择性的乙烯基环丙烷开环/环加成级联。通过基于胱氨酸的二聚体的紫外光促进的均质分解，活性硫基自由基催化剂被原位产生。肽在4-脯氨酸位置的酰胺功能化对于有效的不对称诱导至关重要。立体化学通讯取决于与该取代基的空间相互作用，该相互作用通过H键结合至肽主链而得以实现。

  DOI：

  10.1021/acs.orglett.8b00364

文献信息

• Discovery of a series of novel compounds with moderate anti-hepatitis C virus NS3 protease activity in vitro
  作者：Fangyuan Shi、Yingjie Zhang、Wenfang Xu

  DOI：10.1016/j.bmc.2015.07.032

  日期：2015.9

  The hepatitis C virus (HCV) NS3/4A protease that plays an important role in the viral life cycle has been proven to be an excellent target for the discovery of anti-HCV drugs. Enlightened by some P2-triazole and amide compounds, which had been found as HCV NS3 protease inhibitors, we designed and synthesized a series of novel compounds by incorporating different amino acid residues in P1/P1' and P3/P3' position to develop novel antiviral agents. The result of enzyme inhibition assay indicated that all the designed compounds showed moderate anti-HCV NS3 protease activity. On the basis of the biological result, a detailed structure-activity relationship (SAR) was derived and discussed. (C) 2015 Elsevier Ltd. All rights reserved.
• Disulfide-Bridged Peptides That Mediate Enantioselective Cycloadditions through Thiyl Radical Catalysis
  作者：Jonathan M. Ryss、Amanda K. Turek、Scott J. Miller

  DOI：10.1021/acs.orglett.8b00364

  日期：2018.3.16

  An enantioselective vinylcyclopropane ring-opening/cycloaddition cascade is described. The active thiyl radical catalysts are generated in situ via UV light-promoted homolysis of cystine-based dimers. Amide-functionalization of the peptide at the 4-proline position is essential for effective asymmetric induction. Stereochemical communication is dependent on steric interactions with this substituent

  描述了对映选择性的乙烯基环丙烷开环/环加成级联。通过基于胱氨酸的二聚体的紫外光促进的均质分解，活性硫基自由基催化剂被原位产生。肽在4-脯氨酸位置的酰胺功能化对于有效的不对称诱导至关重要。立体化学通讯取决于与该取代基的空间相互作用，该相互作用通过H键结合至肽主链而得以实现。