methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate | 127379-27-5

• 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: methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate
• 英文别名: (1R,2S,3S,5S)-8-Methyl-3-(4-nitro-phenyl)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester；methyl (1R,2S,3S,5S)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
• CAS: 127379-27-5
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: JWBRJGZNZCKAEB-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3β-(4-aminophenyl)-2β-tropane-2β-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 3-arylecgonine analogs as inhibitors of cocaine binding and dopamine uptake

  摘要：

  3-Arylecgonine analogues were synthesized and characterized by 1H and 13C NMR, IR, and MS. The compounds were synthesized as racemates from cycloheptatriene-7-carboxylic acid or enantiomerically from (-)-cocaine. These analogues were tested for their ability to inhibit [3H]cocaine binding to bovine striatal tissue and to inhibit [3H]dopamine uptake into striatal synaptosomes. Methyl (1RS-2-exo-3-exo)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-ca rboxylate was the most potent analogue. IC50 values for inhibition of cocaine binding and dopamine uptake were 20 and 100 nM, respectively. The racemates and the 1R isomers were equally potent inhibitors of binding and uptake. Methyl (1RS-2-endo-3-exo)-3-(2,4-dinitrophenyl)-8-methyl-8-azabicyclo[3.2 .1]octane- 2-carboxylate was the least potent. IC50 for inhibition of both binding and uptake was 40 microM.

  DOI：

  10.1021/jm00169a036
• 作为产物：
  描述：

  methyl (1R,3S,5S)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-carboxylate 在 硫酸 、 硝酸 作用下， 反应 0.5h， 以80 mg的产率得到methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate
  参考文献：
  名称：

  Synthesis of 3-arylecgonine analogs as inhibitors of cocaine binding and dopamine uptake

  摘要：

  3-Arylecgonine analogues were synthesized and characterized by 1H and 13C NMR, IR, and MS. The compounds were synthesized as racemates from cycloheptatriene-7-carboxylic acid or enantiomerically from (-)-cocaine. These analogues were tested for their ability to inhibit [3H]cocaine binding to bovine striatal tissue and to inhibit [3H]dopamine uptake into striatal synaptosomes. Methyl (1RS-2-exo-3-exo)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-ca rboxylate was the most potent analogue. IC50 values for inhibition of cocaine binding and dopamine uptake were 20 and 100 nM, respectively. The racemates and the 1R isomers were equally potent inhibitors of binding and uptake. Methyl (1RS-2-endo-3-exo)-3-(2,4-dinitrophenyl)-8-methyl-8-azabicyclo[3.2 .1]octane- 2-carboxylate was the least potent. IC50 for inhibition of both binding and uptake was 40 microM.

  DOI：

  10.1021/jm00169a036

文献信息

• KLINE, RICHARD H. (JR);WRIGHT, JEREMY;FOX, KRISTINE M.;ELDEFRAWI, MOHYEE +, J. MED. CHEM., 33,(1990) N, C. 2024-2027
  作者：KLINE, RICHARD H. (JR)、WRIGHT, JEREMY、FOX, KRISTINE M.、ELDEFRAWI, MOHYEE +

  DOI：——

  日期：——
• Synthesis of 3-arylecgonine analogs as inhibitors of cocaine binding and dopamine uptake
  作者：Richard H. Kline、Jeremy Wright、Kristine M. Fox、Mohyee E. Eldefrawi

  DOI：10.1021/jm00169a036

  日期：1990.7

  3-Arylecgonine analogues were synthesized and characterized by 1H and 13C NMR, IR, and MS. The compounds were synthesized as racemates from cycloheptatriene-7-carboxylic acid or enantiomerically from (-)-cocaine. These analogues were tested for their ability to inhibit [3H]cocaine binding to bovine striatal tissue and to inhibit [3H]dopamine uptake into striatal synaptosomes. Methyl (1RS-2-exo-3-exo)-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-2-ca rboxylate was the most potent analogue. IC50 values for inhibition of cocaine binding and dopamine uptake were 20 and 100 nM, respectively. The racemates and the 1R isomers were equally potent inhibitors of binding and uptake. Methyl (1RS-2-endo-3-exo)-3-(2,4-dinitrophenyl)-8-methyl-8-azabicyclo[3.2 .1]octane- 2-carboxylate was the least potent. IC50 for inhibition of both binding and uptake was 40 microM.