(+/-)-2-methyl-3-butyl-8,9-methylenedioxy-2,3,7,11b-tetrahydro-1H-dibenz[de,h]isoquinoline | 679434-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (+/-)-2-methyl-3-butyl-8,9-methylenedioxy-2,3,7,11b-tetrahydro-1H-dibenz[de,h]isoquinoline
• CAS: 679434-37-8
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: FWIBQFACEJMCDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-2-methyl-3-butyl-8,9-methylenedioxy-2,3,7,11b-tetrahydro-1H-dibenz[de,h]isoquinoline 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以54%的产率得到3-Butyl-2-methyl-2,3,7,11b-tetrahydro-1H-dibenzo[de,h]isoquinoline-8,9-diol
  参考文献：
  名称：

  Synthesis and SAR exploration of dinapsoline analogues

  摘要：

  Dinapsoline is a full D-1 dopamine receptor agonist that produces robust otational activity in the unilateral 6-OHDA rat model. This compound is orally active, and shows a low tendency to cause tolerance in rat models. The active enantiomer was determined to have the S-(+) configuration, and the opposite enantiomer is essentially devoid of biological activity. Taken together, dinapsoline has significant metabolic and pharmacological advantages over previous D-1 agonists. In an attempt to define the structure-activity relationships (SARs) and to map out the key elements surrounding the unique structure of dinapsoline, core analogues and substitution analogues of the parent tetracyclic condensed ring structure were prepared. Based on a recently developed synthesis of dinapsoline and its enantiomers, both core and substitution analogues on all four rings (A, B, C and D ring) of dinapsoline were synthesized. It was found that affinity for both D-1 and D-2 receptors was decreased by most substituents on the A, B', and C rings, whereas D ring substitutions preserved much of the dopamine receptor binding activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.015
• 作为产物：
  描述：

  正丁基锂 、 7-Methyl-12H-1,3-dioxa-7-azonia-benzo[fg]cyclopenta[a]anthracene; iodide 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 正己烷 、 乙醚 为溶剂， 反应 1.33h， 生成 (+/-)-2-methyl-3-butyl-8,9-methylenedioxy-2,3,7,11b-tetrahydro-1H-dibenz[de,h]isoquinoline
  参考文献：
  名称：

  Synthesis and SAR exploration of dinapsoline analogues

  摘要：

  Dinapsoline is a full D-1 dopamine receptor agonist that produces robust otational activity in the unilateral 6-OHDA rat model. This compound is orally active, and shows a low tendency to cause tolerance in rat models. The active enantiomer was determined to have the S-(+) configuration, and the opposite enantiomer is essentially devoid of biological activity. Taken together, dinapsoline has significant metabolic and pharmacological advantages over previous D-1 agonists. In an attempt to define the structure-activity relationships (SARs) and to map out the key elements surrounding the unique structure of dinapsoline, core analogues and substitution analogues of the parent tetracyclic condensed ring structure were prepared. Based on a recently developed synthesis of dinapsoline and its enantiomers, both core and substitution analogues on all four rings (A, B, C and D ring) of dinapsoline were synthesized. It was found that affinity for both D-1 and D-2 receptors was decreased by most substituents on the A, B', and C rings, whereas D ring substitutions preserved much of the dopamine receptor binding activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.11.015