3-[9-(2-chlorocarbonylethyl)-9H-fluoren-9-yl]propionyl chloride | 1014698-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 3-[9-(2-chlorocarbonylethyl)-9H-fluoren-9-yl]propionyl chloride
• 英文别名: 3,3'-fluorene-9,9-diyl-di-propionyl chloride；3,3'-Fluoren-9,9-diyl-di-propionylchlorid；3-[9-(3-Chloro-3-oxopropyl)fluoren-9-yl]propanoyl chloride
• CAS: 1014698-27-1
• 化学式: C₁₉H₁₆Cl₂O₂
• 分子量: 347.241
• InChiKey: QRQSGJYFYBWHQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-(4-aminophenyl)tropane-2β-methanol 、 3-[9-(2-chlorocarbonylethyl)-9H-fluoren-9-yl]propionyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以18%的产率得到20-methyl-4,5,7,8,10,14a,15,16,17,18,19,19a-dodecahydro-3H-spiro[16,19-epimino-11,14-ethenocyclohepta[c][1,9]oxaazacyclohexadecine-6,9'-fluorene]-3,9(1H)-dione
  参考文献：
  名称：

  Synthesis and Monoamine Transporter Binding Properties of 2,3-Cyclo Analogues of 3β-(4‘-Aminophenyl)-2β-tropanemethanol

  摘要：

  A series of cyclo-3 beta-(4-aminophenyl)-2 beta-tropanemethanol analogues (5a-m) possessing varying linker groups between the 2- and 3-position on the tropane ring were synthesized and evaluated for their monoamine transporter binding properties. The results show that binding to the dopamine and serotonin transporters (DAT and 5-HTT) is highly dependent on the specific linker used. Cyclo-3 beta-(4-aminophenyl)-2 beta-tropanemethanol pimelic acid ester/amide (5b) had an IC50 of 3.8 nM at the DAT. Cyclo-3 beta-(4-aminophenyl)2 beta-tropanemethanol sebacic acid ester/amide (5e) had a K-i of 1.9 nM at the 5-HTT and was 68- and 737-fold selective for the 5-HTT relative to the DAT and NET. Small changes to the size as well as the electrostatic and hydrophobic properties of the 2,3-linker in 5b or 5e led to much less potent analogues at all three transporters. These results suggest that the high affinity for 5b and 5e at the DAT and 5-HTT may be due to their specific conformational properties.

  DOI：

  10.1021/jm060287w
• 作为产物：
  描述：

  9,9-二(2-氰基乙基)芴 在 氢氧化钾 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 乙二醇 、 苯 为溶剂， 反应 0.5h， 生成 3-[9-(2-chlorocarbonylethyl)-9H-fluoren-9-yl]propionyl chloride
  参考文献：
  名称：

  Synthesis and Monoamine Transporter Binding Properties of 2,3-Cyclo Analogues of 3β-(4‘-Aminophenyl)-2β-tropanemethanol

  摘要：

  A series of cyclo-3 beta-(4-aminophenyl)-2 beta-tropanemethanol analogues (5a-m) possessing varying linker groups between the 2- and 3-position on the tropane ring were synthesized and evaluated for their monoamine transporter binding properties. The results show that binding to the dopamine and serotonin transporters (DAT and 5-HTT) is highly dependent on the specific linker used. Cyclo-3 beta-(4-aminophenyl)-2 beta-tropanemethanol pimelic acid ester/amide (5b) had an IC50 of 3.8 nM at the DAT. Cyclo-3 beta-(4-aminophenyl)2 beta-tropanemethanol sebacic acid ester/amide (5e) had a K-i of 1.9 nM at the 5-HTT and was 68- and 737-fold selective for the 5-HTT relative to the DAT and NET. Small changes to the size as well as the electrostatic and hydrophobic properties of the 2,3-linker in 5b or 5e led to much less potent analogues at all three transporters. These results suggest that the high affinity for 5b and 5e at the DAT and 5-HTT may be due to their specific conformational properties.

  DOI：

  10.1021/jm060287w

文献信息

• DE818940
  申请人：——

  公开号：——

  公开（公告）日：——