(1S,9R,10R)-20-(cyclopropylmethyl)-15-methoxy-6-thia-4,20-diazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),4,12(17),13,15-pentaen-5-amine | 943253-51-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: (1S,9R,10R)-20-(cyclopropylmethyl)-15-methoxy-6-thia-4,20-diazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),4,12(17),13,15-pentaen-5-amine
• CAS: 943253-51-8
• 化学式: C₂₂H₂₇N₃OS
• 分子量: 381.542
• InChiKey: LISKUWZQFNWZBE-LRXVAGHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  79.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,9R,10R)-20-(cyclopropylmethyl)-15-methoxy-6-thia-4,20-diazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),4,12(17),13,15-pentaen-5-amine 在 sodium acetate 、 三溴化硼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 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：

  二氢可待因酮 在 吡啶 、 盐酸 、 氨 、 氢溴酸 、 溴 、 sodium 、 氯甲酸乙酯 、 铜 、 碳酸氢钠 、 potassium carbonate 、 caesium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 112.0h， 生成 (1S,9R,10R)-20-(cyclopropylmethyl)-15-methoxy-6-thia-4,20-diazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),4,12(17),13,15-pentaen-5-amine
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of 6,7-Indolo/Thiazolo-MorphinansFurther SAR of Levorphanol

  摘要：

  To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the delta opioid receptor, while the affinity to kappa and mu receptors was slightly reduced.

  DOI：

  10.1021/jm0701674

文献信息

• Synthesis and Pharmacological Evaluation of 6,7-Indolo/Thiazolo-MorphinansFurther SAR of Levorphanol
  作者：Ao Zhang、Fuying Li、Chunyong Ding、Qizhen Yao、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm0701674

  日期：2007.5.1

  To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the delta opioid receptor, while the affinity to kappa and mu receptors was slightly reduced.
• Synthesis and Pharmacological Evaluation of Aminothiazolomorphinans at the Mu and Kappa Opioid Receptors
  作者：Brian A. Provencher、Anna W. Sromek、Wei Li、Shayla Russell、Elena Chartoff、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm401290y

  日期：2013.11.14

  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.