(6R,6aR,11aS)-9-amino-14-methyl-6,6a,7,11-tetrahydro-5H-6,11a-(epiminoethano)phenanthro[3,2-d]thiazol-2-ol

• 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: (6R,6aR,11aS)-9-amino-14-methyl-6,6a,7,11-tetrahydro-5H-6,11a-(epiminoethano)phenanthro[3,2-d]thiazol-2-ol
• 英文别名: (1S,9R,10R)-5-amino-20-methyl-6-thia-4,20-diazapentacyclo[8.7.3.0^{1,9}.0^{3,7}.0^{12,17}]icosa-3(7),4,12(17),13,15-pentaen-15-ol；(1S,9R,10R)-5-amino-20-methyl-6-thia-4,20-diazapentacyclo[8.7.3.01,9.03,7.012,17]icosa-3(7),4,12(17),13,15-pentaen-15-ol
• 化学式: C₁₈H₂₁N₃OS
• 分子量: 327.45
• InChiKey: LVYYHBPAWFABPE-JCKWVBRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  二氢可待因酮 在 吡啶 、 盐酸 、 氨 、 氢溴酸 、 溴 、 sodium 、 三溴化硼 、 铜 、 caesium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 16.0h， 生成 (6R,6aR,11aS)-9-amino-14-methyl-6,6a,7,11-tetrahydro-5H-6,11a-(epiminoethano)phenanthro[3,2-d]thiazol-2-ol
  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

• [EN] MORPHINAN DERIVATIVES FOR THE TREATMENT OF NEUROPATHIC PAIN<br/>[FR] DÉRIVÉS DE MORPHINANE POUR LE TRAITEMENT DE LA DOULEUR NEUROPATHIQUE
  申请人：NEKTAR THERAPEUTICS

  公开号：WO2016182840A1

  公开（公告）日：2016-11-17

  The present invention relates to compounds and their use as ligands for mu opioid receptors. Also included are methods for preparing the compounds and pharmaceutical compositions containing the compounds. In one or more embodiments of the invention, a compound according to Formula I is provided: and pharmaceutically acceptable salts thereof, wherein R1-R11 are as described herein.

  本发明涉及化合物及其用作阿片μ受体的配体的应用。还包括制备这些化合物的方法和包含这些化合物的药物组合物。在发明的至少一个实施例中，提供了一种根据公式I的化合物：及其药用可接受的盐，其中R1-R11如本文所述。
• Morphinan derivatives for the treatment of neuropathic pain
  申请人：Nektar Therapeutics

  公开号：US10766864B2

  公开（公告）日：2020-09-08

  The present invention relates to compounds and their use as ligands for mu opioid receptors. Also included are methods for preparing the compounds and pharmaceutical compositions containing the compounds. In one or more embodiments of the invention, a compound according to Formula I is provided: and pharmaceutically acceptable salts thereof, wherein R1-R11 are as described herein.

  本发明涉及化合物及其作为μ阿片受体配体的用途。还包括制备这些化合物的方法和含有这些化合物的药物组合物。在本发明的一个或多个实施方案中，提供了根据式 I 的化合物：及其药学上可接受的盐，其中 R1-R11 如本文所述。
• MORPHINAN DERIVATIVES FOR THE TREATMENT OF NEUROPATHIC PAIN
  申请人：Nektar Therapeutics

  公开号：US20180127375A1

  公开（公告）日：2018-05-10

  The present invention relates to compounds and their use as ligands for mu opioid receptors. Also included are methods for preparing the compounds and pharmaceutical compositions containing the compounds. In one or more embodiments of the invention, a compound according to Formula I is provided: and pharmaceutically acceptable salts thereof, wherein R 1 -R 11 are as described herein.
• 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.