3-[4-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)cyclohexyl]-1H-indole-5-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 3-[4-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)cyclohexyl]-1H-indole-5-carbonitrile
• 化学式: C₂₅H₂₇N₃O
• 分子量: 385.509
• InChiKey: OZUHPVAODZNQKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[4-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)cyclohexyl]-1H-indole-5-carbonitrile 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitriles for SERT imaging: Chemical synthesis, evaluation in vitro and radiofluorination

  摘要：

  Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as F-18-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful F-18-fluoroalkylation of one pair of compounds are described herein. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.077
• 作为产物：
  描述：

  6-甲氧基-1,2,3,4-四氢异喹啉 、 4-(5-cyano-1H-indol-3-yl)-cyclohexanone 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 3-[4-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)cyclohexyl]-1H-indole-5-carbonitrile 、 3-[4-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)cyclohexyl]-1H-indole-5-carbonitrile
  参考文献：
  名称：

  3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitriles for SERT imaging: Chemical synthesis, evaluation in vitro and radiofluorination

  摘要：

  Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as F-18-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful F-18-fluoroalkylation of one pair of compounds are described herein. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.077

文献信息

• [EN] TETRAHYDROISOQUINOLINYL-INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION<br/>[FR] DERIVES DE TETRAHYDROISOQUINOLINYL-INDOLE POUR LE TRAITEMENT DE LA DEPRESSION
  申请人：AMERICAN HOME PROD

  公开号：WO2000064886A1

  公开（公告）日：2000-11-02

  Compounds are provided which have formula (I) wherein: R1, R2, R3, and R4 are, independently, hydrogen, halogen, alkoxy, or carboxamide; R5 is hydrogen, halogen, CF3, CN, carbamide or alkoxy; and X is (CH2)n or a 4-6 membered carbocyclic ring, wherein n is an integer of 2 to 4; or pharmaceutically acceptable salts thereof.

  提供了化学式为（I）的化合物，其中：R1、R2、R3和R4分别为氢、卤素、烷氧基或羧酰胺基；R5为氢、卤素、三氟甲基、氰基、尿素基或烷氧基；X为（CH2）n或4-6个成员的碳环，其中n为2至4的整数；或其药学上可接受的盐。
• TETRAHYDROISOQUINOLINYL-INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1171434A1

  公开（公告）日：2002-01-16
• US6245780B1
  申请人：——

  公开号：US6245780B1

  公开（公告）日：2001-06-12
• 3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitriles for SERT imaging: Chemical synthesis, evaluation in vitro and radiofluorination
  作者：Uta Funke、Steffen Fischer、Achim Hiller、Matthias Scheunemann、Winnie Deuther-Conrad、Peter Brust、Jörg Steinbach

  DOI：10.1016/j.bmcl.2008.06.077

  日期：2008.8

  Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as F-18-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful F-18-fluoroalkylation of one pair of compounds are described herein. (C) 2008 Elsevier Ltd. All Fights reserved.