4-Bromo-N-[2-(3,4-dihydro-2(1H)-isoquinolinyl)ethyl]-1-methoxy-2-naphthalenecarboxamide | 669067-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Bromo-N-[2-(3,4-dihydro-2(1H)-isoquinolinyl)ethyl]-1-methoxy-2-naphthalenecarboxamide
• 英文别名: 4-bromo-N-[2-(3,4-dihydro-1H-isoquinolin-2-yl)ethyl]-1-methoxynaphthalene-2-carboxamide
• CAS: 669067-81-6
• 化学式: C₂₃H₂₃BrN₂O₂
• 分子量: 439.352
• InChiKey: LQOYFQQIZFEVDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(3,4-二氢-1H-异喹啉-2-基)乙腈 生成 4-Bromo-N-[2-(3,4-dihydro-2(1H)-isoquinolinyl)ethyl]-1-methoxy-2-naphthalenecarboxamide
  参考文献：
  名称：

  Conformationally-flexible benzamide analogues as dopamine D3 and σ2 receptor ligands

  摘要：

  A series of conformationally-flexible analogues was prepared and their affinities for D2-like dopamine(D-2, D-3 and D-4) were determined using in vitro radioligand binding assays. The results of this structure-activity relationship study identified one compound, 15, that bound with high affinity (K-i value = 2 nM) and moderate selectivity (30-fold) for D-3 compared to D-2 receptors. In addition, this series of compounds were also tested for affinity at sigma(1) and sigma(2) receptors. We evaluated the affinity of these dopaminergic compounds at sigma receptors because (a) several antipsychotic drugs, which are high affinity antagonists at dopamine D2-like receptors, also bind to sigma receptors and (b) sigma receptors are expressed ubiquitously and at high levels (picomoles per mg proteins). It was observed that a number of analogues displayed high affinity and excellent selectivity for sigma(2) versus sigma(1) receptors. Consequently, these novel compounds may be useful for characterizing the functional role of sigma(2) receptors and for imaging the sigma(2) receptor status of tumors in vivo with PET. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.083

文献信息

• SIGMA-2 RECEPTOR RADIOTRACERS FOR IMAGING THE PROLIFERATIVE STATUS OF SOLID TUMORS
  申请人：Mach Robert

  公开号：US20090041663A1

  公开（公告）日：2009-02-12

  Novel benzamide compounds of Formula (I), Formula (II), and Formula (III), salts, water soluble salts, analogs and radiolabeled counterparts thereof as sigma-2 receptor radiotracers for imaging the proliferative status of solid tumors. A method for diagnosing a mammal for the presence of a mammalian tumor therein comprises administering to the mammal a diagnostic imaging detectable effective amount of a benzamide compound having a structure illustrated in Formula (I), Formula (II) and Formula (III) and detecting binding of the compound to a tumor in the mammal. A method for diagnostic imaging of a mammalian tissue having cell surface sigma-2 receptors comprising administering to a mammal a diagnostic imaging amount of a compound having a structure illustrated in Formula (I) Formula (II) and Formula (III) and detecting an image of a tissue having an ample cells with sigma-2 receptors.
• DETECTION OF CANCER CELLS IN VITRO USING SIGMA-2 RECEPTOR LIGANDS AS RADIOTRACERS
  申请人：Mach Robert

  公开号：US20100028936A1

  公开（公告）日：2010-02-04

  Methods for detection of cancer cells and for determining the proliferative status of cells in a tissue sample in vitro are disclosed. These methods comprise contacting a tissue sample with a radiolabeled compound or salt thereof of Formula wherein at least one of X, Y, and Z comprises a radioisotope, n is an integer from 2 to about 10; and each of A and A 1 is a C 1 -C 4 alkoxyl, a C 1 -C 4 fluoroalkyl or a C 1 -C 4 fluoroalkoxyl. The methods further comprise detecting the distribution of the radioisotope in the tissue sample, whereby a cell having a high density of the radioisotope compared to quiescent cells is diagnostic for a cancer cell.
• US7390902B2
  申请人：——

  公开号：US7390902B2

  公开（公告）日：2008-06-24
• US7612206B2
  申请人：——

  公开号：US7612206B2

  公开（公告）日：2009-11-03
• US7893266B2
  申请人：——

  公开号：US7893266B2

  公开（公告）日：2011-02-22