methyl (3S,4S)-4-(4-((2-methylquinolin-4-yl)methoxy)benzamido)pyrrolidine-3-carboxylate | 362488-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl (3S,4S)-4-(4-((2-methylquinolin-4-yl)methoxy)benzamido)pyrrolidine-3-carboxylate
• CAS: 362488-46-8
• 化学式: C₂₄H₂₅N₃O₄
• 分子量: 419.48
• InChiKey: NEFHTSVUYPLXRP-RBBKRZOGSA-N

物化性质

• 沸点：
  637.7±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  89.55
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (3S,4S)-4-(4-((2-methylquinolin-4-yl)methoxy)benzamido)pyrrolidine-3-carboxylate 在 氢氧化钾 、 羟胺 作用下， 以 甲醇 为溶剂， 生成 (3S,4S)-N-hydroxy-4-({4-[(2-methyl-4-quinolinyl)methoxy]benzoyl}amino)-3-pyrrolidinecarboxamide
  参考文献：
  名称：

  α,β-Cyclic-β-benzamido hydroxamic acids: Novel templates for the design, synthesis, and evaluation of selective inhibitors of TNF-α converting enzyme (TACE)

  摘要：

  Selective inhibitors of TNF-alpha Converting Enzyme (TACE) based on (1R,2S)-cyclopentyl, (3S,4S)-pyrrolidinyl, and (3R,4S)-tetrahydrofuranyl beta-benzamido hydroxamic acids have been synthesized and evaluated. This study has led to the discovery of novel inhibitors whose profiles include activity against TACE in an enzyme assay, potency in the suppression of LPS-stimulated TNF-alpha in human whole blood, selectivity against a panel of MMPs and oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.059
• 作为产物：
  描述：

  1-O-tert-butyl 3-O-methyl (3S,4S)-4-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]pyrrolidine-1,3-dicarboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到methyl (3S,4S)-4-(4-((2-methylquinolin-4-yl)methoxy)benzamido)pyrrolidine-3-carboxylate
  参考文献：
  名称：

  α,β-Cyclic-β-benzamido hydroxamic acids: Novel templates for the design, synthesis, and evaluation of selective inhibitors of TNF-α converting enzyme (TACE)

  摘要：

  Selective inhibitors of TNF-alpha Converting Enzyme (TACE) based on (1R,2S)-cyclopentyl, (3S,4S)-pyrrolidinyl, and (3R,4S)-tetrahydrofuranyl beta-benzamido hydroxamic acids have been synthesized and evaluated. This study has led to the discovery of novel inhibitors whose profiles include activity against TACE in an enzyme assay, potency in the suppression of LPS-stimulated TNF-alpha in human whole blood, selectivity against a panel of MMPs and oral bioavailability. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.059