[bis(1-methylethyl)amino]carbodithioic acid 5-isoquinolinyl ester | 679433-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: [bis(1-methylethyl)amino]carbodithioic acid 5-isoquinolinyl ester
• 英文别名: isoquinolin-5-yl N,N-di(propan-2-yl)carbamodithioate
• CAS: 679433-69-3
• 化学式: C₁₆H₂₀N₂S₂
• 分子量: 304.48
• InChiKey: NQLPOLWSIHPAAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  438.7±37.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  16.13
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [bis(1-methylethyl)amino]carbodithioic acid 5-isoquinolinyl ester 在 盐酸 、 sodium hydroxide 、 偶氮二异丁腈 、 三正丁基氢锡 、 三溴化硼 、 sodium cyanoborohydride 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 38.75h， 生成 1,2,3,11b-tetrahydro[1]benzothiopyrano[4,3,2-de]isoquinolin-8,9-diol hydrobromide
  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：

  5-溴异喹啉 、 四异丙基二硫化秋兰姆 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.25h， 生成 [bis(1-methylethyl)amino]carbodithioic acid 5-isoquinolinyl ester
  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