methyl (2R,4S)-1-(3,4-dichlorophenylsulfonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylate | 1408186-54-8

• 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: methyl (2R,4S)-1-(3,4-dichlorophenylsulfonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylate
• 英文别名: methyl (2R,4S)-1-(3,4-dichlorophenyl)sulfonyl-4-(4-phenyltriazol-1-yl)pyrrolidine-2-carboxylate
• CAS: 1408186-54-8
• 化学式: C₂₀H₁₈Cl₂N₄O₄S
• 分子量: 481.359
• InChiKey: ADHRPJHVWJUUJM-IFXJQAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2R,4S)-1-(3,4-dichlorophenylsulfonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylate 在 盐酸羟胺 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以49%的产率得到(2R,4S)-1-(3,4-dichlorophenylsulfonyl)-N-hydroxy-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  d-Proline-based peptidomimetic inhibitors of anthrax lethal factor

  摘要：

  In this work we reported the generation of D-proline-derived hydroxamic acids as inhibitors of anthrax lethal factor (LF), taking advantage of a pyrrolidine ring as the central scaffold and a hydroxamate group as the Zn2+ chelating agent. The introduction of two hydrophobic groups addressing the S1' subsite and a long substrate-binding groove was conceived by overlapping the bioactive conformations of two reported LF inhibitors. Micromolar affinity of compound 38 suggested cis-3-substituted-1-sulfonamido-D-proline hydroxamic acids as a promising class of peptidomimetic inhibitors for developing novel LF inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.028
• 作为产物：
  描述：

  顺式-4-羟基-D-脯氨酸甲酯 在 4-二甲氨基吡啶 、 sodium azide 、 copper diacetate 、 sodium ascorbate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 2.0h， 生成 methyl (2R,4S)-1-(3,4-dichlorophenylsulfonyl)-4-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  d-Proline-based peptidomimetic inhibitors of anthrax lethal factor

  摘要：

  In this work we reported the generation of D-proline-derived hydroxamic acids as inhibitors of anthrax lethal factor (LF), taking advantage of a pyrrolidine ring as the central scaffold and a hydroxamate group as the Zn2+ chelating agent. The introduction of two hydrophobic groups addressing the S1' subsite and a long substrate-binding groove was conceived by overlapping the bioactive conformations of two reported LF inhibitors. Micromolar affinity of compound 38 suggested cis-3-substituted-1-sulfonamido-D-proline hydroxamic acids as a promising class of peptidomimetic inhibitors for developing novel LF inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.028

文献信息

• d-Proline-based peptidomimetic inhibitors of anthrax lethal factor
  作者：Chiara Calugi、Andrea Trabocchi、Claudia Lalli、Antonio Guarna

  DOI：10.1016/j.ejmech.2012.08.028

  日期：2012.10

  In this work we reported the generation of D-proline-derived hydroxamic acids as inhibitors of anthrax lethal factor (LF), taking advantage of a pyrrolidine ring as the central scaffold and a hydroxamate group as the Zn2+ chelating agent. The introduction of two hydrophobic groups addressing the S1' subsite and a long substrate-binding groove was conceived by overlapping the bioactive conformations of two reported LF inhibitors. Micromolar affinity of compound 38 suggested cis-3-substituted-1-sulfonamido-D-proline hydroxamic acids as a promising class of peptidomimetic inhibitors for developing novel LF inhibitors. (C) 2012 Elsevier Masson SAS. All rights reserved.