5-(tributylstannyl)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide | 123266-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-(tributylstannyl)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide
• 英文别名: 7-Benzofurancarboxamide, N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydro-5-(tributylstannyl)-, (S)-；N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-tributylstannyl-2,3-dihydro-1-benzofuran-7-carboxamide
• CAS: 123266-60-4
• 化学式: C₂₈H₄₈N₂O₂Sn
• 分子量: 563.411
• InChiKey: SMFFGYWAXFUUCZ-AHJYMZSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(tributylstannyl)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-2,3-dihydrobenzofuran-7-carboxamide 在 盐酸 、 sodium iodide 、 双氧水 作用下， 以 水 为溶剂， 反应 0.5h， 生成 N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-(125I)iodanyl-2,3-dihydro-1-benzofuran-7-carboxamide
  参考文献：
  名称：

  Synthesis and characterization of iodobenzamide analogs: potential D-2 dopamine receptor imaging agents

  摘要：

  (S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-3-iodo-6- methoxybenzamide ([123I]IBZM) is a central nervous system (CNS) D-2 dopamine receptor imaging agent. In order to investigate the versatility of this parent structure in specific dopamine receptor localization and the potential for developing new dopamine receptor imaging agents, a series of new iodinated benzamides with fused ring systems, naphthalene (INAP) and benzofuran (IBF), was synthesized and radiolabeled, and the in vivo and in vitro biological properties were characterized. The best analogue of IBZM is IBF (21). The specific binding of [125I]IBF (21) with rat striatal tissue preparation was found to be saturable and displayed a Kd of 0.106 +/- 0.015 nM. Competition data of various receptor ligands for [125I]IBF (21) binding show the following rank order of potency: spiperone greater than IBF (21) greater than IBZM greater than (+)-butaclamol greater than (+/-)-ADTN,6,7 greater than ketanserin greater than SCH-23390 much greater than propranolol. The in vivo biodistribution results confirm that [125I]IBF (21) concentrated in the striatal area after iv injection into rats. The study demonstrates that [123I]IBF (21) is a potential agent for imaging CNS D-2 dopamine receptors.

  DOI：

  10.1021/jm00163a029
• 作为产物：
  描述：

  (-)-(S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydrobenzo[b]furan-7-carboxamide 、 六正丁基二锡 以46%的产率得到
  参考文献：
  名称：

  MURPHY, RAYMOND A.;KUNG, HANK F.;KUNG, MEI-PING;BILLINGS, JEFFREY, J. MED. CHEM., 33,(1990) N, C. 171-178

  摘要：

  DOI：