(4-bromo-2-nitrophenyl)(2-dimethylaminomethylphenyl)methanol | 780766-43-0

• 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: (4-bromo-2-nitrophenyl)(2-dimethylaminomethylphenyl)methanol
• 英文别名: (4-bromo-2-nitrophenyl)-[2-[(dimethylamino)methyl]phenyl]methanol
• CAS: 780766-43-0
• 化学式: C₁₆H₁₇BrN₂O₃
• 分子量: 365.227
• InChiKey: PKHFRGIWUGQDKO-UHFFFAOYSA-N

物化性质

• 沸点：
  484.9±40.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-bromo-2-nitrophenyl)(2-dimethylaminomethylphenyl)methanol 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到5-bromo-2-(2-(dimethylaminomethyl)benzyl)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
• 作为产物：
  描述：

  4-溴-2-硝基苯甲醛 、 (2-溴苯基)二甲胺 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以12%的产率得到(4-bromo-2-nitrophenyl)(2-dimethylaminomethylphenyl)methanol
  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

• Diphenyl ether derivatives and their use for imaging serotonin transporters
  申请人：Kung F. Hank

  公开号：US20060083680A1

  公开（公告）日：2006-04-20

  This invention relates to diphenyl ether derivatives and their use in imaging of Serotonin Transporters (SERTS). The present invention also provides diagnostic compositions comprising the compounds of the present invention, and a pharmaceutically acceptable carrier or diluent. The invention further provides a method of imaging SERTS, comprising introducing into a patient a detectable quantity of a labeled compound of the present invention, or a pharmaceutically acceptable salt, ester, amide or prodrug thereof, allowing sufficient time for the labeled compound to associate with one or more SERTs, and detecting the labeled compound. The present invention can also be used to follow the progression of a disease associated with SERTs or a therapy that targets SERTs.

  本发明涉及二苯醚衍生物及其在血清素转运体（SERTS）成像中的应用。本发明还提供了包含本发明化合物的诊断组合物，并且还提供了一种含有药学上可接受的载体或稀释剂的成像SERTS的方法，该方法包括向患者引入本发明的标记化合物或其药学上可接受的盐，酯，酰胺或前药的可检测量，允许足够的时间使标记化合物与一个或多个SERTs结合，并检测标记化合物。本发明还可用于跟踪与SERTs相关的疾病的进展或针对SERTs的治疗。
• [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).