MCL-445

• 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-445
• 英文别名: 1-[(1R,9R,10R)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-yl]-3-methylurea
• 化学式: C₂₃H₃₃N₃O
• 分子量: 367.535
• InChiKey: URMRSPJBIISGIL-XKCSPQBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  44.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  异氰酸甲酯 、 MCL-182 在 sodium 作用下， 以 四氢呋喃 为溶剂， 以78.6%的产率得到MCL-445
  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

文献信息

• In-vitro investigation of oxazol and urea analogues of morphinan at opioid receptors
  作者：Xuemei Peng、Brian I. Knapp、Jean M. Bidlack、John L. Neumeyer

  DOI：10.1016/j.bmc.2007.03.076

  日期：2007.6

  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.