4-(5-formyl-2,4-dimethyl-1H-pyrrole-3-carbonyl)piperazine-1-carboxylic acid tert-butyl ester | 1202780-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(5-formyl-2,4-dimethyl-1H-pyrrole-3-carbonyl)piperazine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 4-(5-formyl-2,4-dimethyl-1H-pyrrole-3-carbonyl)piperazine-1-carboxylate
• CAS: 1202780-12-8
• 化学式: C₁₇H₂₅N₃O₄
• 分子量: 335.403
• InChiKey: ULVQOZAKSCRCMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chloro-phenyl)-methyl-amide 、 4-(5-formyl-2,4-dimethyl-1H-pyrrole-3-carbonyl)piperazine-1-carboxylic acid tert-butyl ester 在 四氢吡咯 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以78%的产率得到4-(5-{5-[(3-chlorophenyl)methylsulfonyl]-2-oxodihydroindol-3-ylidenemethyl}-2,4-dimethyl-1H-pyrrole-3-carbonyl)piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  In Vivo Positron Emission Tomography (PET) Imaging of Mesenchymal−Epithelial Transition (MET) Receptor

  摘要：

  We report the radiosynthesis and evaluation of 3-[3,5-dimethyl-4-(4-[C-11]methylpiperazinecarbonyl)-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chlorophenyl)methylamide, termed [(11)]SU11274 ([C-11]14) for in vivo imaging of mesenchymal-epithelial transition (MET) receptor by positron emission tomography (PET). Following the synthesis of the precursor (13) that was achieved in 10 steps with a total yield of 9.7%, [C-11]14 was obtained through radiomethylation in a range of 5-10% radiochemical yield and over 95% radiochemical purity. For in vivo PET Studies, two human lung cancer xenograft models were established using MET-positive NCI-H1975 and MET-negative NCI-H520 cell lines. Quantitative [C-11]14-PET studies showed that the tumor uptake of [C-11]14 in the NCI-H1975 xenografts was significantly higher than that in the NCI-H520 xenografts, which is consistent with their corresponding immunohistochemical tissue staining patterns of MET receptors from the same animals, These studies demonstrated that [C-11]14-PET is an appropriate imaging marker for quantification of MET receptor in vivo, which can facilitate efficacy evaluation in the clinical development of MET-targeted cancer therapeutics.

  DOI：

  10.1021/jm900803q
• 作为产物：
  描述：

  2,4-二甲基-5-醛基-1H-吡咯-3-羧酸 、 N-Boc-哌嗪 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以63%的产率得到4-(5-formyl-2,4-dimethyl-1H-pyrrole-3-carbonyl)piperazine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  In Vivo Positron Emission Tomography (PET) Imaging of Mesenchymal−Epithelial Transition (MET) Receptor

  摘要：

  We report the radiosynthesis and evaluation of 3-[3,5-dimethyl-4-(4-[C-11]methylpiperazinecarbonyl)-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chlorophenyl)methylamide, termed [(11)]SU11274 ([C-11]14) for in vivo imaging of mesenchymal-epithelial transition (MET) receptor by positron emission tomography (PET). Following the synthesis of the precursor (13) that was achieved in 10 steps with a total yield of 9.7%, [C-11]14 was obtained through radiomethylation in a range of 5-10% radiochemical yield and over 95% radiochemical purity. For in vivo PET Studies, two human lung cancer xenograft models were established using MET-positive NCI-H1975 and MET-negative NCI-H520 cell lines. Quantitative [C-11]14-PET studies showed that the tumor uptake of [C-11]14 in the NCI-H1975 xenografts was significantly higher than that in the NCI-H520 xenografts, which is consistent with their corresponding immunohistochemical tissue staining patterns of MET receptors from the same animals, These studies demonstrated that [C-11]14-PET is an appropriate imaging marker for quantification of MET receptor in vivo, which can facilitate efficacy evaluation in the clinical development of MET-targeted cancer therapeutics.

  DOI：

  10.1021/jm900803q

文献信息

• In Vivo Positron Emission Tomography (PET) Imaging of Mesenchymal−Epithelial Transition (MET) Receptor
  作者：Chunying Wu、Zhe Tang、Weiwen Fan、Wenxia Zhu、Changning Wang、Edurado Somoza、Norbert Owino、Ruoshi Li、Patrick C. Ma、Yanming Wang

  DOI：10.1021/jm900803q

  日期：2010.1.14

  We report the radiosynthesis and evaluation of 3-[3,5-dimethyl-4-(4-[C-11]methylpiperazinecarbonyl)-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chlorophenyl)methylamide, termed [(11)]SU11274 ([C-11]14) for in vivo imaging of mesenchymal-epithelial transition (MET) receptor by positron emission tomography (PET). Following the synthesis of the precursor (13) that was achieved in 10 steps with a total yield of 9.7%, [C-11]14 was obtained through radiomethylation in a range of 5-10% radiochemical yield and over 95% radiochemical purity. For in vivo PET Studies, two human lung cancer xenograft models were established using MET-positive NCI-H1975 and MET-negative NCI-H520 cell lines. Quantitative [C-11]14-PET studies showed that the tumor uptake of [C-11]14 in the NCI-H1975 xenografts was significantly higher than that in the NCI-H520 xenografts, which is consistent with their corresponding immunohistochemical tissue staining patterns of MET receptors from the same animals, These studies demonstrated that [C-11]14-PET is an appropriate imaging marker for quantification of MET receptor in vivo, which can facilitate efficacy evaluation in the clinical development of MET-targeted cancer therapeutics.