3β-[4-(4-bromo-thiophen-3-yl)-phenyl]tropane-2β-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 3β-[4-(4-bromo-thiophen-3-yl)-phenyl]tropane-2β-carboxylic acid methyl ester
• 英文别名: methyl (1R,2S,3S,5S)-3-[4-(4-bromothiophen-3-yl)phenyl]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• 化学式: C₂₀H₂₂BrNO₂S
• 分子量: 420.37
• InChiKey: AKZNIBWGGYEGKL-SFUIVIKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  六甲基二锡 、 (1R,2S,3S,5S)-3-(4-碘苯基)-8-甲基-8-氮杂双环[3.2.1]辛烷-2-羧酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 四(三苯基膦)钯 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 生成 3β-[4-(4-bromo-thiophen-3-yl)-phenyl]tropane-2β-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and monoamine transporter affinity of new 2β-carbomethoxy-3β-[4-(substituted thiophenyl)]phenyltropanes: discovery of a selective SERT antagonist with picomolar potency

  摘要：

  Preparation of cocaine analogues has been aimed largely at development of stable compounds with high affinity and selectivity for the dopamine transporter (DAT). We now report the synthesis and monoamine transporter affinity of 10 new 2beta-carbomethoxy-3p-[4-(substituted thiophenyl)]phenyltropanes. Among these, compound 4b exhibited very high affinity for the serotonin transporter (SERT: K-i = 17 pM) and good selectivity over dopamine (DAT: 710-fold) and norepinephrine transporters (NET: 11,100-fold). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.014

文献信息

• Tropane analogs binding to monoamine transporters
  申请人：——

  公开号：US20030013883A1

  公开（公告）日：2003-01-16

  The present invention is directed to a tropane analog having the structure (I) 1 wherein Ar is a selected substituted or unsubstituted aryl group; G═CO 2 CH 3 , COR, or CH═CHR; X═H, I, Br, Cl, F, NO 2 , COR, or, NH 2 ; R═H or a substituted or unsubstituted lower alkyl group; and Z═O, S, or N. The tropane analogs of the invention bind to monoamine transporters in the mammalian brain, and are useful as diagnostic tools for analyzing the role of monoamine transporters in diseases such as depression, schizophrenia, major depression, attention-deficit hyperactivity disorder, obesity, obsessive compulsive disorders, and cocaine addiction.

  本发明涉及一种具有结构（I）的曲梨酮类似物，其中Ar是选定的取代或未取代芳基；G是CO2CH3、COR或CH2CHR；X是H、I、Br、Cl、F、NO2、COR或NH2；R是H或取代或未取代的较低烷基；Z是O、S或N。本发明的曲梨酮类似物结合到哺乳动物大脑中的单胺转运体，可作为分析单胺转运体在疾病如抑郁症、精神分裂症、重度抑郁症、注意力缺陷多动障碍、肥胖、强迫性障碍和可卡因成瘾等疾病中的作用的诊断工具。