(-)-(S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydrobenzo[b]furan-7-carboxamide | 108551-45-7

• 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: (-)-(S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydrobenzo[b]furan-7-carboxamide
• 英文别名: 5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydrobenzofuran-7-carboxamide；5-bromo-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide
• CAS: 108551-45-7
• 化学式: C₁₆H₂₁BrN₂O₂
• 分子量: 353.259
• InChiKey: VRMUQJZSWAAYCB-ZDUSSCGKSA-N

物化性质

• 熔点：
  52-54 °C
• 沸点：
  420.6±45.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  (-)-(S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydrobenzo[b]furan-7-carboxamide 在 四(三苯基膦)钯 、 碘 、 palladium diacetate 、 六正丁基二锡 、 三乙胺 作用下， 生成 N-[[(2S)-1-乙基吡咯烷-2-基]甲基]-5-碘-2,3-二氢-1-苯并呋喃-7-甲酰胺
  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：

  2,3-二氢苯并呋喃 在 正丁基锂 、 氯化亚砜 、 溴 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 (-)-(S)-5-bromo-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,3-dihydrobenzo[b]furan-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

文献信息

• Potential antipsychotic agents. 7. Synthesis and antidopaminergic properties of the atypical highly potent (S)-5-bromo-2,3-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide and related compounds. A comparative study
  作者：Thomas Hoegberg、Tomas De Paulis、Lars Johansson、Yatendra Kumar、Haakan Hall、Sven Ove Oegren

  DOI：10.1021/jm00170a040

  日期：1990.8

  (S)-5-Bromo-2,3-dimethoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide (6) and some related compounds, i.e. the R isomer 7, the 3-hydroxy analogue 8, the desbromo derivative 9, the monomethoxy compound 10, and the 2,4-dimethoxy analogue 11, have been synthesized from the corresponding benzoic acids. The benzamides, lacking o-hydroxy groups, were evaluated for their affinity for the [3H]spiperone binding

  （S）-5-溴-2,3-二甲氧基-N-[（1-乙基-2-吡咯烷基）甲基]苯甲酰胺（6）和一些相关化合物，即R异构体7、3-羟基类似物8​​，由相应的苯甲酸合成去溴衍生物9，单甲氧基化合物10和2，4-二甲氧基类似物11。评估缺少邻羟基的苯甲酰胺对[3H] spiperone结合位点的亲和力，以及与相应水杨酰胺作用有关的对阿扑吗啡诱导的行为反应的抑制作用。除了2-羟基-3-甲氧基苯甲酰胺12和相关的1,4-苯并二恶烷（13）和2,3-二氢苯并呋喃（14）外，还研究了羧酰胺，以评估受体对2-甲氧基的立体电子要求相互作用。该研究支持以下观点：邻甲氧基可以采用共面和垂直方向，并维持生物活性构象中所需的分子内氢键。在体外和体内，均发现苯甲酰胺6与类似的高活性水杨酰胺3（FLB 463）等价。另外，6显示出对行为综合症的多动成分的优先抑制，这被认为表明在抗精神病有效剂量下，人诱发锥体束外副作用的趋势较
• MURPHY, RAYMOND A.;KUNG, HANK F.;KUNG, MEI-PING;BILLINGS, JEFFREY, J. MED. CHEM., 33,(1990) N, C. 171-178
  作者：MURPHY, RAYMOND A.、KUNG, HANK F.、KUNG, MEI-PING、BILLINGS, JEFFREY

  DOI：——

  日期：——
• HOGBERG, THOMAS;DE, PAULIS TOMAS;JOHANSSON, LARS;KUMAR, YATENDRA;HALL, HA+, J. MED. CHEM., 33,(1990) N, C. 2305-2309
  作者：HOGBERG, THOMAS、DE, PAULIS TOMAS、JOHANSSON, LARS、KUMAR, YATENDRA、HALL, HA+

  DOI：——

  日期：——
• Synthesis and characterization of iodobenzamide analogs: potential D-2 dopamine receptor imaging agents
  作者：Raymond A. Murphy、Hank F. Kung、Mei Ping Kung、Jeffrey Billings

  DOI：10.1021/jm00163a029

  日期：1990.1

  (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.