5-(3-fluorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo<2,1-a>isoindole | 27097-45-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-(3-fluorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo<2,1-a>isoindole
• 英文别名: 5-(m-Fluorphenyl)-5-hydroxy-2,3-dihydro-5H-imidazo<2,1-a>isoindol；5-(3'-Fluorphenyl)-5-hydroxy-2,3-dihydro-5H-imidazo<2,1-a>isoindol；5-(3-fluoro-phenyl)-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol；5-(3-Fluorophenyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol
• CAS: 27097-45-6
• 化学式: C₁₆H₁₃FN₂O
• 分子量: 268.29
• InChiKey: JWWLTRDKVHXMRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基咪唑啉 、 3-氟苯甲酸乙酯 在 正丁基锂 作用下， 生成 5-(3-fluorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo<2,1-a>isoindole
  参考文献：
  名称：

  Synthesis of halogenated analogs of 5-(4-chlorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo[2,1-a]-isoindole or mazindol for exploration of the dopamine transporter

  摘要：

  In order to study the presynaptic dopamine transporter in the human brain by single photon emission tomography (SPET) or positron emission tomography (PET) we have developed new halogenated mazindol derivatives using a pathway involving a reaction between a dilithio derivative of 2-phenyl-2-imidazoline and appropriate methyl or ethyl halogenobenzoates. After HPLC purification and chemical characterization, the affinity for the dopamine transporter was studied in vitro with [H-3]-GBR 12935 and compared to mazindol and nomifensine. Affinity potencies were determined as follow:- mazindol > brominated derivatives > iodinated derivatives > nomifensine > fluorinated derivatives. The properties were related tot eh structure of these compounds and showed the importance of the nature of the substituent on the primary phenyl ring of mazindol for affinity to the dopamine transporter.

  DOI：

  10.1016/0223-5234(93)90047-i

文献信息

• AEBERLI P.; EDEN P.; GOGERTY J. H.; HOULIHAN W. J.; PENBERTHY C., J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 2, 177-182
  作者：AEBERLI P.、 EDEN P.、 GOGERTY J. H.、 HOULIHAN W. J.、 PENBERTHY C.

  DOI：——

  日期：——
• US4148906A
  申请人：——

  公开号：US4148906A

  公开（公告）日：1979-04-10
• US4202897A
  申请人：——

  公开号：US4202897A

  公开（公告）日：1980-05-13
• Synthesis of halogenated analogs of 5-(4-chlorophenyl)-2,3-dihydro-5-hydroxy-5H-imidazo[2,1-a]-isoindole or mazindol for exploration of the dopamine transporter
  作者：E Galinier、L Garreau、AM Dognon、JE Ombetta-Goka、Y Frangin、S Chalon、JC Besnard、D Guilloteau

  DOI：10.1016/0223-5234(93)90047-i

  日期：1993.1

  In order to study the presynaptic dopamine transporter in the human brain by single photon emission tomography (SPET) or positron emission tomography (PET) we have developed new halogenated mazindol derivatives using a pathway involving a reaction between a dilithio derivative of 2-phenyl-2-imidazoline and appropriate methyl or ethyl halogenobenzoates. After HPLC purification and chemical characterization, the affinity for the dopamine transporter was studied in vitro with [H-3]-GBR 12935 and compared to mazindol and nomifensine. Affinity potencies were determined as follow:- mazindol > brominated derivatives > iodinated derivatives > nomifensine > fluorinated derivatives. The properties were related tot eh structure of these compounds and showed the importance of the nature of the substituent on the primary phenyl ring of mazindol for affinity to the dopamine transporter.