Methyl 2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1-(4-phenylmethoxyphenyl)pyrrolidin-3-yl]acetate | 300856-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: Methyl 2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1-(4-phenylmethoxyphenyl)pyrrolidin-3-yl]acetate
• CAS: 300856-61-5
• 化学式: C₂₅H₃₀N₂O₆
• 分子量: 454.523
• InChiKey: UOUDBTRXASIDSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1-(4-phenylmethoxyphenyl)pyrrolidin-3-yl]acetate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 Methyl 2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1-(4-phenylmethoxyphenyl)pyrrolidin-3-yl]pent-4-enoate
  参考文献：
  名称：

  Discovery of N-Hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  New inhibitors of tumor necrosis factor-a converting enzyme (TACE) were discovered using an N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamide scaffold. The series was found to be potent in a porcine TACE (pTACE) assay with IC50S typically below 5 nM. For most compounds, selectivity for pTACE relative to MMP-1,-2, and -9 is at least 300-fold. Compound 2o was potent in inhibition of TNFalpha production in a human whole blood assay (WBA) with an IC50 of 0.42 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00313-5
• 作为产物：
  描述：

  N-BOC-L-天冬氨酸 1-甲基酯 在 三乙酰氧基硼氢化钠 、 potassium carbonate 、 臭氧 、 lithium diisopropyl amide 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 Methyl 2-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-1-(4-phenylmethoxyphenyl)pyrrolidin-3-yl]acetate
  参考文献：
  名称：

  Discovery of N-Hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  New inhibitors of tumor necrosis factor-a converting enzyme (TACE) were discovered using an N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamide scaffold. The series was found to be potent in a porcine TACE (pTACE) assay with IC50S typically below 5 nM. For most compounds, selectivity for pTACE relative to MMP-1,-2, and -9 is at least 300-fold. Compound 2o was potent in inhibition of TNFalpha production in a human whole blood assay (WBA) with an IC50 of 0.42 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00313-5

文献信息

• Discovery of N-Hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)
  作者：James J.-W. Duan、Zhonghui Lu、Chu-Biao Xue、Xiaohua He、Jennifer L. Seng、John J. Roderick、Zelda R. Wasserman、Rui-Qin Liu、Maryanne B. Covington、Ronald L. Magolda、Robert C. Newton、James M. Trzaskos、Carl P. Decicco

  DOI：10.1016/s0960-894x(03)00313-5

  日期：2003.6

  New inhibitors of tumor necrosis factor-a converting enzyme (TACE) were discovered using an N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamide scaffold. The series was found to be potent in a porcine TACE (pTACE) assay with IC50S typically below 5 nM. For most compounds, selectivity for pTACE relative to MMP-1,-2, and -9 is at least 300-fold. Compound 2o was potent in inhibition of TNFalpha production in a human whole blood assay (WBA) with an IC50 of 0.42 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.