3-[3,5-dimethyl-4-(piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chlorophenyl)methylamide hydrochloride | 1202780-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[3,5-dimethyl-4-(piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chlorophenyl)methylamide hydrochloride
• 英文别名: N-(3-chlorophenyl)-3-[[3,5-dimethyl-4-(piperazine-1-carbonyl)-1H-pyrrol-2-yl]methylidene]-N-methyl-2-oxo-1H-indole-5-sulfonamide;hydrochloride
• CAS: 1202780-14-0
• 化学式: C₂₇H₂₈ClN₅O₄S*ClH
• 分子量: 590.53
• InChiKey: KAWLOZXJPHRBGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  114.61
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [11C]methyl iodide 、 3-[3,5-dimethyl-4-(piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chlorophenyl)methylamide hydrochloride 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 [(11)C]SU11274
  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：

  4-(5-{5-[(3-chlorophenyl)methylsulfonyl]-2-oxodihydroindol-3-ylidenemethyl}-2,4-dimethyl-1H-pyrrole-3-carbonyl)piperazine-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以74%的产率得到3-[3,5-dimethyl-4-(piperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-2-oxo-2,3-dihydro-1H-indole-5-sulfonic acid (3-chlorophenyl)methylamide hydrochloride
  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