(4bS,9R)-3-methoxy-11-methyl-6-oxo-6,7,8,8a,9,10-hexahydro-5H-9,4b- (epiminoethano)phenanthren-4-yl trifluoromethanesulfonate | 1227681-13-1

• 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: (4bS,9R)-3-methoxy-11-methyl-6-oxo-6,7,8,8a,9,10-hexahydro-5H-9,4b- (epiminoethano)phenanthren-4-yl trifluoromethanesulfonate
• 英文别名: (4bS,9R)-3-methoxy-11-methyl-6-oxo-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthren-4-yl trifluoromethanesulfonate
• CAS: 1227681-13-1
• 化学式: C₁₉H₂₂F₃NO₅S
• 分子量: 433.449
• InChiKey: GPBXYUZTNKJDHS-IYOUNJFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.79
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4bS,9R)-3-methoxy-11-methyl-6-oxo-6,7,8,8a,9,10-hexahydro-5H-9,4b- (epiminoethano)phenanthren-4-yl trifluoromethanesulfonate 在 甲酸 、 ethyl chloroformate 、 1,3-双(二苯基膦)丙烷 、 氢溴酸 、 溴 、 sodium acetate 、 palladium diacetate 、 三溴化硼 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 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：

  可待因 在 正丁基锂 、 palladium on activated charcoal 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (4bS,9R)-3-methoxy-11-methyl-6-oxo-6,7,8,8a,9,10-hexahydro-5H-9,4b- (epiminoethano)phenanthren-4-yl trifluoromethanesulfonate
  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

文献信息

• Rapid access to morphinones: removal of 4,5-ether bridge with Pd-catalyzed triflate reduction
  作者：Christopher D. Hupp、John L. Neumeyer

  DOI：10.1016/j.tetlet.2010.02.146

  日期：2010.4

  A new synthetic method for the removal of the 4,5-bridged ether moiety of several opioids has been developed. This process offers a faster, simpler synthetic route to obtain the morphinone scaffold in high yields without the need for protection of the ketone moiety.

  已经开发出一种用于去除几种阿片类药物的 4,5-桥接醚部分的新合成方法。该过程提供了一种更快、更简单的合成途径，以高产率获得吗啡酮支架，而无需保护酮部分。
• [EN] MORPHAN AND MORPHINAN ANALOGUES, AND METHODS OF USE<br/>[FR] ANALOGUES DE MORPHANE ET MORPHINANE, ET PROCÉDÉS D'UTILISATION
  申请人：ALKERMES PHARMA IRELAND LTD

  公开号：WO2014190270A1

  公开（公告）日：2014-11-27

  The present application relates to analogues of morphan and morphinan, compositions thereof, and methods for treating a disease or condition comprising administering an effective amount of the compounds or compositions to a subject in need thereof.

  本申请涉及吗啡烷和吗啡喃的类似物，其组合物，以及治疗疾病或病症的方法，包括向需要其的受试者施用有效量的该化合物或组合物。