methyl (2R,4R)-1-(3,4-dichlorophenylsulfonyl)-4-hydroxypyrrolidine-2-carboxylate | 1408186-45-7

• 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,4R)-1-(3,4-dichlorophenylsulfonyl)-4-hydroxypyrrolidine-2-carboxylate
• 英文别名: methyl (2R,4R)-1-(3,4-dichlorophenyl)sulfonyl-4-hydroxypyrrolidine-2-carboxylate
• CAS: 1408186-45-7
• 化学式: C₁₂H₁₃Cl₂NO₅S
• 分子量: 354.211
• InChiKey: FYHIYQMMWMCGFQ-RDDDGLTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2R,4R)-1-(3,4-dichlorophenylsulfonyl)-4-hydroxypyrrolidine-2-carboxylate 在 sodium azide 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 2.58h， 生成 methyl (2R,4R)-1-[(3,4-dichlorophenyl)sulfonyl]-4-((E)-3-(furan-2-yl)acrylamido)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
• 作为产物：
  描述：

  顺式-4-羟基-D-脯氨酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl (2R,4R)-1-(3,4-dichlorophenylsulfonyl)-4-hydroxypyrrolidine-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