3-[4'-trimethylammoniobenzylidene]indoline-2-one trifluoromethansulfonate | 1202637-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[4'-trimethylammoniobenzylidene]indoline-2-one trifluoromethansulfonate
• CAS: 1202637-65-7
• 化学式: CF₃O₃S*C₁₈H₁₉N₂O
• 分子量: 428.432
• InChiKey: CMGUCVSZOCQZDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.3
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[4'-trimethylammoniobenzylidene]indoline-2-one trifluoromethansulfonate 在 potassium [¹⁸F]fluoride 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以8.4%的产率得到3-[4-(18)F-fluorobenzylidene]indolin-2-one
  参考文献：
  名称：

  Synthesis and radiopharmacological investigation of 3-[4′-[18F]fluorobenzylidene]indolin-2-one as possible tyrosine kinase inhibitor

  摘要：

  The radiosynthesis and radiopharmacological evaluation of 3-[4'-[F-18] fluorobenzylidene]indolin-2-one, a derivative of tyrosine kinase inhibitor SU5416, is described. The radiosynthesis was accomplished by Knoevenagel condensation of 4-[F-18]fluorobenzaldehyde with oxindole in a remotely controlled synthesis module. The reaction conditions were optimized through screening the influence of different bases on the radiochemical yield. The radiotracer was obtained after a two-step labelling procedure in 4% decay-corrected radiochemical yield at a specific activity of 48-61 GBq/mu mol within 90 min. The radiochemical purity after semi-preparative HPLC purification exceeded 98%.The biodistribution was studied in Wistar rats. After distribution the radiotracer was rapidly accumulated in the adrenals, liver and kidneys, however, it was cleared from these and the most other organs. Only the adipose tissue remained the activity over 60 min. Unexpected high transient uptake was observed in the brain, pancreas, heart and lung. The fast clearance of 3-[4'-[F-18] fluorobenzylidene] indolin-2-one was caused by excretion, approximately one half each was renal and biliary excreted and the other part cleared by metabolic processes. In arterial blood plasma two more polar metabolites were found by radio-HPLC. After 20 min post-injection, only 12% of intact radiotracer has been detected. Consequently, in small animal PET studies with FaDu tumour bearing mice no specific uptake in the tumours could be observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.038
• 作为产物：
  描述：

  （3Z）-3-[[[4-（二甲基氨基）苯基]亚甲基]-1H-吲哚-2-酮 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 24.0h， 以92%的产率得到3-[4'-trimethylammoniobenzylidene]indoline-2-one trifluoromethansulfonate
  参考文献：
  名称：

  Synthesis and radiopharmacological investigation of 3-[4′-[18F]fluorobenzylidene]indolin-2-one as possible tyrosine kinase inhibitor

  摘要：

  The radiosynthesis and radiopharmacological evaluation of 3-[4'-[F-18] fluorobenzylidene]indolin-2-one, a derivative of tyrosine kinase inhibitor SU5416, is described. The radiosynthesis was accomplished by Knoevenagel condensation of 4-[F-18]fluorobenzaldehyde with oxindole in a remotely controlled synthesis module. The reaction conditions were optimized through screening the influence of different bases on the radiochemical yield. The radiotracer was obtained after a two-step labelling procedure in 4% decay-corrected radiochemical yield at a specific activity of 48-61 GBq/mu mol within 90 min. The radiochemical purity after semi-preparative HPLC purification exceeded 98%.The biodistribution was studied in Wistar rats. After distribution the radiotracer was rapidly accumulated in the adrenals, liver and kidneys, however, it was cleared from these and the most other organs. Only the adipose tissue remained the activity over 60 min. Unexpected high transient uptake was observed in the brain, pancreas, heart and lung. The fast clearance of 3-[4'-[F-18] fluorobenzylidene] indolin-2-one was caused by excretion, approximately one half each was renal and biliary excreted and the other part cleared by metabolic processes. In arterial blood plasma two more polar metabolites were found by radio-HPLC. After 20 min post-injection, only 12% of intact radiotracer has been detected. Consequently, in small animal PET studies with FaDu tumour bearing mice no specific uptake in the tumours could be observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.038