5-bromo-2-[(2-dimethylaminomethyl)phenoxy]phenylamine | 780766-38-3

• 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: 5-bromo-2-[(2-dimethylaminomethyl)phenoxy]phenylamine
• 英文别名: 5-Bromo-2-[2-[(dimethylamino)methyl]phenoxy]aniline
• CAS: 780766-38-3
• 化学式: C₁₅H₁₇BrN₂O
• 分子量: 321.217
• InChiKey: SAVXDBXSNYOYEX-UHFFFAOYSA-N

物化性质

• 沸点：
  365.5±42.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-2-[(2-dimethylaminomethyl)phenoxy]phenylamine 在 四(三苯基膦)钯 、 三乙胺 、 碘 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 8.0h， 以21.3 mg的产率得到2-(2-(dimethylaminomethyl)phenoxy)-5-iodophenylamine
  参考文献：
  名称：

  2-(2-(Dimethylaminomethyl)phenoxy)-5-iodophenylamine:  An Improved Serotonin Transporter Imaging Agent

  摘要：

  Imaging serotonin transporters (SERT) is an emerging research tool potentially useful to cast light on the mechanisms of drug action as well as to monitor the treatment of depressed patients. We have prepared two new derivatives of 3, 2-(2-(dimethylaminomethyl)phenoxy)-5-iodophenylamine (4) and 2-(2-(dimethylaminomethyl)benzyl)-5-iodophenylamine (5) (K-i for SERT = 0.37 and 48.6 nM, respectively). Both [I-125]4 and [I-125]5 displayed excellent brain uptakes in rats, and they showed a highest uptake in hypothalamus (between 60 and 240 min), a region populated with the highest density of SERT. The specific uptake of [I-125]4 in the hypothalamus resulted in a target to nontarget ratio ([hypothalamus-cerebellum]/cerebellum) of 4.3 at 2 h. Autoradiography of rat brain sections (ex vivo at 2 h) of [I-125]4 showed an excellent regional distribution pattern consistent with known SERT localization. These data suggest that [I-123]4 may be useful for imaging SERT binding sites in the brain by single photon emission computed tomography (SPECT).

  DOI：

  10.1021/jm049917p
• 作为产物：
  描述：

  2,5-二溴硝基苯 在 盐酸 、 氢氧化钾 、 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 8.5h， 生成 5-bromo-2-[(2-dimethylaminomethyl)phenoxy]phenylamine
  参考文献：
  名称：

  2-(2-(Dimethylaminomethyl)phenoxy)-5-iodophenylamine:  An Improved Serotonin Transporter Imaging Agent

  摘要：

  Imaging serotonin transporters (SERT) is an emerging research tool potentially useful to cast light on the mechanisms of drug action as well as to monitor the treatment of depressed patients. We have prepared two new derivatives of 3, 2-(2-(dimethylaminomethyl)phenoxy)-5-iodophenylamine (4) and 2-(2-(dimethylaminomethyl)benzyl)-5-iodophenylamine (5) (K-i for SERT = 0.37 and 48.6 nM, respectively). Both [I-125]4 and [I-125]5 displayed excellent brain uptakes in rats, and they showed a highest uptake in hypothalamus (between 60 and 240 min), a region populated with the highest density of SERT. The specific uptake of [I-125]4 in the hypothalamus resulted in a target to nontarget ratio ([hypothalamus-cerebellum]/cerebellum) of 4.3 at 2 h. Autoradiography of rat brain sections (ex vivo at 2 h) of [I-125]4 showed an excellent regional distribution pattern consistent with known SERT localization. These data suggest that [I-123]4 may be useful for imaging SERT binding sites in the brain by single photon emission computed tomography (SPECT).

  DOI：

  10.1021/jm049917p

文献信息

• [EN] DIPHENYL ETHER DERIVATIVES AND THEIR USE FOR IMAGING SEROTONIN TRANSPORTERS<br/>[FR] DERIVES DE DIPHENYLE ETHER ET LEUR UTILISATION POUR IMAGER DES TRANSPORTEURS DE SEROTONINE
  申请人：UNIV PENNSYLVANIA

  公开号：WO2006029303A3

  公开（公告）日：2006-06-08
• 2-(2-(Dimethylaminomethyl)phenoxy)-5-iodophenylamine:  An Improved Serotonin Transporter Imaging Agent
  作者：Hank F. Kung、Suzanne Newman、Seok-Rye Choi、Shunichi Oya、Catherine Hou、Zhi-Ping Zhuang、Paul D. Acton、Karl Plössl、Jeffrey Winkler、Mei-Ping Kung

  DOI：10.1021/jm049917p

  日期：2004.10.1

  Imaging serotonin transporters (SERT) is an emerging research tool potentially useful to cast light on the mechanisms of drug action as well as to monitor the treatment of depressed patients. We have prepared two new derivatives of 3, 2-(2-(dimethylaminomethyl)phenoxy)-5-iodophenylamine (4) and 2-(2-(dimethylaminomethyl)benzyl)-5-iodophenylamine (5) (K-i for SERT = 0.37 and 48.6 nM, respectively). Both [I-125]4 and [I-125]5 displayed excellent brain uptakes in rats, and they showed a highest uptake in hypothalamus (between 60 and 240 min), a region populated with the highest density of SERT. The specific uptake of [I-125]4 in the hypothalamus resulted in a target to nontarget ratio ([hypothalamus-cerebellum]/cerebellum) of 4.3 at 2 h. Autoradiography of rat brain sections (ex vivo at 2 h) of [I-125]4 showed an excellent regional distribution pattern consistent with known SERT localization. These data suggest that [I-123]4 may be useful for imaging SERT binding sites in the brain by single photon emission computed tomography (SPECT).