(6R,6aR,11aS)-9-acetamido-14-(cyclopropylmethyl)-6,6a,7,11-tetrahydro-5H-6,11a-(epiminoethano)phenanthro[3,2-d]thiazol-2-yl acetate | 1476060-53-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (6R,6aR,11aS)-9-acetamido-14-(cyclopropylmethyl)-6,6a,7,11-tetrahydro-5H-6,11a-(epiminoethano)phenanthro[3,2-d]thiazol-2-yl acetate
• CAS: 1476060-53-3
• 化学式: C₂₅H₂₉N₃O₃S
• 分子量: 451.59
• InChiKey: GFEVGADLHYZHHV-NIRIFSCTSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.53
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (6R,6aR,11aS)-9-acetamido-14-(cyclopropylmethyl)-6,6a,7,11-tetrahydro-5H-6,11a-(epiminoethano)phenanthro[3,2-d]thiazol-2-yl acetate 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 以8 mg的产率得到6,7-(2-N-methyl)aminothiazolo-N-cyclopropylmethyl-morphin-3-ol
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Aminothiazolomorphinans at the Mu and Kappa Opioid Receptors

  摘要：

  Previous studies with aminothiazolomorphinans suggested that this class of opioid ligands may be useful as a potential pharmacotherapeutic to decrease drug abuse. Novel aminothiazole derivatives of cyclorphan were prepared to evaluate a series of aminothiazolomorphinans with, varying pharmacological properties at the kappa opioid receptor (KOR) and mu opioid receptor (MOR). This study was focused on exploring the regioisomeric analogs with the aminothiazole on the C-ring of the morphinan skeleton. Receptor binding and [S-35]GTP gamma S binding assays were used to characterize the affinity and pharmacological properties of the aminothiazolomorphinans. Intracranial self-stimulation (ICSS) was used to compare the effects of a representative aminothiazolomorphinan with the morphinan mixed-KOR/MOR agonist butorphan (MCL-101) on brain-stimulation reward.

  DOI：

  10.1021/jm401290y
• 作为产物：
  描述：

  可待因 在 正丁基锂 、 甲酸 、 ethyl chloroformate 、 palladium on activated charcoal 、 1,3-双(二苯基膦)丙烷 、 氢溴酸 、 氢气 、 溴 、 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (6R,6aR,11aS)-9-acetamido-14-(cyclopropylmethyl)-6,6a,7,11-tetrahydro-5H-6,11a-(epiminoethano)phenanthro[3,2-d]thiazol-2-yl acetate
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Aminothiazolomorphinans at the Mu and Kappa Opioid Receptors

  摘要：

  Previous studies with aminothiazolomorphinans suggested that this class of opioid ligands may be useful as a potential pharmacotherapeutic to decrease drug abuse. Novel aminothiazole derivatives of cyclorphan were prepared to evaluate a series of aminothiazolomorphinans with, varying pharmacological properties at the kappa opioid receptor (KOR) and mu opioid receptor (MOR). This study was focused on exploring the regioisomeric analogs with the aminothiazole on the C-ring of the morphinan skeleton. Receptor binding and [S-35]GTP gamma S binding assays were used to characterize the affinity and pharmacological properties of the aminothiazolomorphinans. Intracranial self-stimulation (ICSS) was used to compare the effects of a representative aminothiazolomorphinan with the morphinan mixed-KOR/MOR agonist butorphan (MCL-101) on brain-stimulation reward.

  DOI：

  10.1021/jm401290y