(R)-(+)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-3-chloropropanamide | 220832-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-(+)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-3-chloropropanamide
• 英文别名: 3-chloro-N-[(1R)-5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl]propanamide
• CAS: 220832-22-4
• 化学式: C₁₄H₁₈ClNO₂
• 分子量: 267.755
• InChiKey: CEUDOWZFZMJEHV-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-甲氧苯基)哌嗪 、 (R)-(+)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-3-chloropropanamide 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 以81%的产率得到3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-N-((R)-5-methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-propionamide
  参考文献：
  名称：

  1-Aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl]piperazines and Their Analogues:  Influence of the Stereochemistry of the Tetrahydronaphthalen-1-yl Nucleus on 5-HT_1A Receptor Affinity and Selectivity versus α₁ and D₂ Receptors. 5

  摘要：

  Some 1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazines and their alkylamino and alkylamido analogues, previously studied as 5-HT1A ligands, were prepared in enantiomerically pure form, and their absolute configuration was det;ermined by chemical correlation or by chiroptical properties. They were evaluated for in vitro 5-HT1A, D-2, and alpha(1) receptor affinity by radioligand binding assays, to study the influence of the chiral carbon atom of the tetrahydronaphthalene nucleus on the 5-HT1A affinity and selectivity. Results indicated that, as regarding the 5-HT1A receptor affinity, there was no difference in affinity between (-)- and (+)-enantiomers as well as the racemate of each compound. The stereochemistry, instead, influenced the selectivity: all (-)-enantiomers displayed affinity values higher than those of (+)-isomers at D-2 receptors, and conversely, all (+)-enantiomers displayed affinity values higher than those of (-)-isomers at alpha(1) receptors. As a result of this trend, it is not possible to predict the isomer with a better selectivity profile. However, compounds (S)-(+)-2, (S)-(+)-4, and (R)-(+)-6 displayed high affinity for the 5-HT1A receptor (IC50 values ranging between 7.0 and 2.3 nM) and good selectivity (greater than or equal to 250-fold) versus both D-2 and alpha(1) receptors. Furthermore, compounds (S)-(+)-4 and (R)-(-)-4 were submitted to the [S-35]GTP gamma S binding assay for a preliminary evaluation of their intrinsic activity on the 5-HT1A receptor.

  DOI：

  10.1021/jm980420n
• 作为产物：
  描述：

  5-甲氧基-1-四氢萘胺 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R)-(+)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-3-chloropropanamide
  参考文献：
  名称：

  1-Aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl]piperazines and Their Analogues:  Influence of the Stereochemistry of the Tetrahydronaphthalen-1-yl Nucleus on 5-HT_1A Receptor Affinity and Selectivity versus α₁ and D₂ Receptors. 5

  摘要：

  Some 1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazines and their alkylamino and alkylamido analogues, previously studied as 5-HT1A ligands, were prepared in enantiomerically pure form, and their absolute configuration was det;ermined by chemical correlation or by chiroptical properties. They were evaluated for in vitro 5-HT1A, D-2, and alpha(1) receptor affinity by radioligand binding assays, to study the influence of the chiral carbon atom of the tetrahydronaphthalene nucleus on the 5-HT1A affinity and selectivity. Results indicated that, as regarding the 5-HT1A receptor affinity, there was no difference in affinity between (-)- and (+)-enantiomers as well as the racemate of each compound. The stereochemistry, instead, influenced the selectivity: all (-)-enantiomers displayed affinity values higher than those of (+)-isomers at D-2 receptors, and conversely, all (+)-enantiomers displayed affinity values higher than those of (-)-isomers at alpha(1) receptors. As a result of this trend, it is not possible to predict the isomer with a better selectivity profile. However, compounds (S)-(+)-2, (S)-(+)-4, and (R)-(+)-6 displayed high affinity for the 5-HT1A receptor (IC50 values ranging between 7.0 and 2.3 nM) and good selectivity (greater than or equal to 250-fold) versus both D-2 and alpha(1) receptors. Furthermore, compounds (S)-(+)-4 and (R)-(-)-4 were submitted to the [S-35]GTP gamma S binding assay for a preliminary evaluation of their intrinsic activity on the 5-HT1A receptor.

  DOI：

  10.1021/jm980420n

文献信息

• Amino-1,3,5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators.
  申请人：Bayer CropScience AG

  公开号：EP2305655A2

  公开（公告）日：2011-04-06

  Amino-1,3,5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators. The invention relates to an optically active compound of formula (I) or a salt thereof: wherein the various symbols are as defined in the description, to proceses for their preparation, to compositions thereof, and to their use as herbicides or plant growth regulators. The invention also relates to novel intermediates of formula (III), (V) and (XIII) as defined in the description.

  N-取代手性双环基的氨基-1,3,5-三嗪、其制备工艺、其组合物及其作为除草剂和植物生长调节剂的用途。 本发明涉及一种具有光学活性的式 (I) 化合物或其盐： 其中各种符号如描述中所定义，涉及其制备工艺、其组合物及其作为除草剂或植物生长调节剂的用途。本发明还涉及如描述中所定义的式 (III)、(V) 和 (XIII) 的新型中间体。
• 1-Aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)alkyl]piperazines and Their Analogues:  Influence of the Stereochemistry of the Tetrahydronaphthalen-1-yl Nucleus on 5-HT_1A Receptor Affinity and Selectivity versus α₁ and D₂ Receptors. 5
  作者：Roberto Perrone、Francesco Berardi、Nicola A. Colabufo、Marcello Leopoldo、Vincenzo Tortorella

  DOI：10.1021/jm980420n

  日期：1999.2.1

  Some 1-aryl-4-[(5-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)-n-propyl]piperazines and their alkylamino and alkylamido analogues, previously studied as 5-HT1A ligands, were prepared in enantiomerically pure form, and their absolute configuration was det;ermined by chemical correlation or by chiroptical properties. They were evaluated for in vitro 5-HT1A, D-2, and alpha(1) receptor affinity by radioligand binding assays, to study the influence of the chiral carbon atom of the tetrahydronaphthalene nucleus on the 5-HT1A affinity and selectivity. Results indicated that, as regarding the 5-HT1A receptor affinity, there was no difference in affinity between (-)- and (+)-enantiomers as well as the racemate of each compound. The stereochemistry, instead, influenced the selectivity: all (-)-enantiomers displayed affinity values higher than those of (+)-isomers at D-2 receptors, and conversely, all (+)-enantiomers displayed affinity values higher than those of (-)-isomers at alpha(1) receptors. As a result of this trend, it is not possible to predict the isomer with a better selectivity profile. However, compounds (S)-(+)-2, (S)-(+)-4, and (R)-(+)-6 displayed high affinity for the 5-HT1A receptor (IC50 values ranging between 7.0 and 2.3 nM) and good selectivity (greater than or equal to 250-fold) versus both D-2 and alpha(1) receptors. Furthermore, compounds (S)-(+)-4 and (R)-(-)-4 were submitted to the [S-35]GTP gamma S binding assay for a preliminary evaluation of their intrinsic activity on the 5-HT1A receptor.