MCL 188

• 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: MCL 188
• 英文别名: (1S,5R,16R,17S,20R)-11-amino-4-methyl-15-oxa-10-thia-4,12-diazahexacyclo[12.6.1.01,16.05,20.07,21.09,13]henicosa-7,9(13),11,14(21),18-pentaen-17-ol
• 化学式: C₁₈H₁₉N₃O₂S
• 分子量: 341.434
• InChiKey: JMHDFWBYKDLFLC-YWDMBHFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7,8-didehydro-6-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4,5-epoxy-17-methyl-(5α,6α)-morphinan-3-amine 在 四丁基氟化铵 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 MCL 188
  参考文献：
  名称：

  2-Aminothiazole-Derived Opioids. Bioisosteric Replacement of Phenols

  摘要：

  A series of aminothiazole-derived morphinans, benzomorphans, and morphine were synthesized. Although their affinities were somewhat lower than their phenol prototypes, one compound (9a, ATPM) has been identified possessing high affinity and selectivity at the kappa receptor. Functional assays showed that 9a was a full kappa but partial mu agonist; the efficacy at kappa was significantly greater than at mu receptors. This novel compound may be valuable for the development of long-acting analgesics and drug abuse medication.

  DOI：

  10.1021/jm049978n

文献信息

• 2-Aminothiazole-Derived Opioids. Bioisosteric Replacement of Phenols
  作者：Ao Zhang、Wennan Xiong、James E. Hilbert、Emily K. DeVita、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1021/jm049978n

  日期：2004.4.1

  A series of aminothiazole-derived morphinans, benzomorphans, and morphine were synthesized. Although their affinities were somewhat lower than their phenol prototypes, one compound (9a, ATPM) has been identified possessing high affinity and selectivity at the kappa receptor. Functional assays showed that 9a was a full kappa but partial mu agonist; the efficacy at kappa was significantly greater than at mu receptors. This novel compound may be valuable for the development of long-acting analgesics and drug abuse medication.