12-methoxy-7-methyl-6,7,8,9,10,15-hexahydro-5H-dibenzo[d,g]azacycloundecene | 951388-04-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 12-methoxy-7-methyl-6,7,8,9,10,15-hexahydro-5H-dibenzo[d,g]azacycloundecene
• 英文别名: 17-methoxy-11-methyl-11-azatricyclo[13.4.0.03,8]nonadeca-1(15),3,5,7,16,18-hexaene
• CAS: 951388-04-8
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: CNKNJMJEVKMFAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-methoxy-7-methyl-6,7,8,9,10,15-hexahydro-5H-dibenzo[d,g]azacycloundecene 、 氯甲酸乙酯 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 ethyl 12-methoxy-5,6,8,9,10,15-hexahydro-7H-dibenzo[d,g]azacycloundecine-7-carboxylate
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 16. Expanding Dibenz[d,g]azecines to 11- and 12-Membered Homologues. Interaction with Dopamine D₁−D₅ Receptors

  摘要：

  Oxygenated 7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecines are potent dopamine receptor antagonists, preferentially at D-1/D-5. We synthesized the hydroxylated, methoxylated, and chlorinated 11-membered and 12-membered homologues of these 10-membered heterocycles. Their affinities for the human cloned D-1-D-5 receptors (radioligand binding) and functionalities (calcium assay) were measured. Enlarging the dibenzazecines to the corresponding dibenzazacycloundecenes and dibenzazacyclododecenes generally maintains the high antagonistic affinity for D-1/D-5 but also leads to a compound with a clozapine-like binding profile due to additional affinity for D-4.

  DOI：

  10.1021/jm070388+
• 作为产物：
  描述：

  ethyl 12-methoxy-5,6,8,9,10,15-hexahydro-7H-dibenzo[d,g]azacycloundecine-7-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以73%的产率得到12-methoxy-7-methyl-6,7,8,9,10,15-hexahydro-5H-dibenzo[d,g]azacycloundecene
  参考文献：
  名称：

  Dopamine/Serotonin Receptor Ligands. 16. Expanding Dibenz[d,g]azecines to 11- and 12-Membered Homologues. Interaction with Dopamine D₁−D₅ Receptors

  摘要：

  Oxygenated 7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecines are potent dopamine receptor antagonists, preferentially at D-1/D-5. We synthesized the hydroxylated, methoxylated, and chlorinated 11-membered and 12-membered homologues of these 10-membered heterocycles. Their affinities for the human cloned D-1-D-5 receptors (radioligand binding) and functionalities (calcium assay) were measured. Enlarging the dibenzazecines to the corresponding dibenzazacycloundecenes and dibenzazacyclododecenes generally maintains the high antagonistic affinity for D-1/D-5 but also leads to a compound with a clozapine-like binding profile due to additional affinity for D-4.

  DOI：

  10.1021/jm070388+

文献信息

• Dopamine/Serotonin Receptor Ligands. 16. Expanding Dibenz[<i>d,g</i>]azecines to 11- and 12-Membered Homologues. Interaction with Dopamine D₁−D₅ Receptors
  作者：Christoph Enzensperger、Franziska K. U. Müller、Bärbel Schmalwasser、Petra Wiecha、Heidi Traber、Jochen Lehmann

  DOI：10.1021/jm070388+

  日期：2007.9.1

  Oxygenated 7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecines are potent dopamine receptor antagonists, preferentially at D-1/D-5. We synthesized the hydroxylated, methoxylated, and chlorinated 11-membered and 12-membered homologues of these 10-membered heterocycles. Their affinities for the human cloned D-1-D-5 receptors (radioligand binding) and functionalities (calcium assay) were measured. Enlarging the dibenzazecines to the corresponding dibenzazacycloundecenes and dibenzazacyclododecenes generally maintains the high antagonistic affinity for D-1/D-5 but also leads to a compound with a clozapine-like binding profile due to additional affinity for D-4.