2-amino-3-hydroxy-N-(cyclobutylmethyl)morphinan | 938051-30-0

• 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: 2-amino-3-hydroxy-N-(cyclobutylmethyl)morphinan
• CAS: 938051-30-0
• 化学式: C₂₁H₃₀N₂O
• 分子量: 326.482
• InChiKey: WAPACVQEQPQGCA-LDQXTDLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.49
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-amino-3-hydroxy-N-(cyclobutylmethyl)morphinan 、 二(1氢-咪唑基)亚胺 以 四氢呋喃 为溶剂， 以38.6%的产率得到MCL-454
  参考文献：
  名称：

  In-vitro investigation of oxazol and urea analogues of morphinan at opioid receptors

  摘要：

  A series of 2-amino-oxazole (7 and 8) analogs and 2-one-oxazole analogs (9 and 10) were synthesized from cyclorpban (1) or butorphan (2) and evaluated in-vitro by their binding affinity at mu, delta, and kappa opioid receptors and compared with their 2-aminothiozole analogs 5 and 6. Ligands 7-10 showed decreased affinities at kappa and mu receptors. Urea analogs (11-14) were also prepared from 2-aminocyclorphan (3) or 2-aminobutorphan (4) and evaluated in-vitro by their binding affinity at mu, delta, and kappa opioid receptors. The urea derived opioids retained their affinities at mu receptors while showing increased affinities at 6 receptors and decreased affinities at K receptors. Functional activities of these compounds were measured in the [S-35]GTP(gamma)S binding assay, illustrating that all of these ligands were kappa agonists. At the mu receptor, compounds 11 and 12 were mu agonist/antagonists. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.076
• 作为产物：
  描述：

  2-amino-3-hydroxy-N-(cyclobutylmethyl)morphinan 在 palladium on activated charcoal 甲酸 、 ammonium formate 作用下， 以 乙醇 为溶剂， 以94%的产率得到2-amino-3-hydroxy-N-(cyclobutylmethyl)morphinan
  参考文献：
  名称：

  In-vitro investigation of oxazol and urea analogues of morphinan at opioid receptors

  摘要：

  A series of 2-amino-oxazole (7 and 8) analogs and 2-one-oxazole analogs (9 and 10) were synthesized from cyclorpban (1) or butorphan (2) and evaluated in-vitro by their binding affinity at mu, delta, and kappa opioid receptors and compared with their 2-aminothiozole analogs 5 and 6. Ligands 7-10 showed decreased affinities at kappa and mu receptors. Urea analogs (11-14) were also prepared from 2-aminocyclorphan (3) or 2-aminobutorphan (4) and evaluated in-vitro by their binding affinity at mu, delta, and kappa opioid receptors. The urea derived opioids retained their affinities at mu receptors while showing increased affinities at 6 receptors and decreased affinities at K receptors. Functional activities of these compounds were measured in the [S-35]GTP(gamma)S binding assay, illustrating that all of these ligands were kappa agonists. At the mu receptor, compounds 11 and 12 were mu agonist/antagonists. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.03.076