N-allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol methanesulfonate | 77386-13-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: N-allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol methanesulfonate
• 英文别名: SKF 85174 mesylate；9-Chloro-5-(4-hydroxyphenyl)-3-prop-2-enyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol;methanesulfonic acid
• CAS: 77386-13-1
• 化学式: CH₄O₃S*C₁₉H₂₀ClNO₃
• 分子量: 441.933
• InChiKey: UJPDJVFELBMGHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol methanesulfonate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以80%的产率得到6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-n-propyl-3-benzazepine-7,8-diol methanesulfonate
  参考文献：
  名称：

  Dopamine receptor agonists: 3-allyl-6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-diol and a series of related 3-benzazepines

  摘要：

  The N-allyl derivative (SK&F 85174) of 6-chloro-2,3,4,5-tetrahydro-1-(4-hydroxyphenyl)-1H-3-benzazepine-7,8-dio l (SK&F 82526) not only retains the exceptional D-1 agonist potency of its parent but also displays reasonably potent D-2 agonist activity, as measured by a dopamine-sensitive adenylate cyclase test and a rabbit ear artery assay, respectively. Several additional N-substituted compounds were prepared to explore the D-2/D-1 agonist relationship. The N-methyl analogue retained good D-2 agonist potency, but this substitution converted D-1 agonist activity into antagonist activity. Most other N-substituents sharply decreased D-2 agonist potency including the N-n-propyl group. This observation was surprising since the introduction of mono- or di-N-n-propyl substituent(s) is commonly linked with retention or enhancement of D-2 agonist potency in other series of dopamine agonists. The N-(2-hydroxyethyl) analogue retains about one-fourth the D-2 potency of SK&F 85174. Several synthetic methods were used to prepare these compounds. N-Allylation of a trimethoxybenzazepine followed by cleavage of the methyl ethers with boron tribromide was the preferred method. Other methods used were direct alkylation of the trihydroxy secondary amine, i.e., SK&F 82526, and an acylation-amide reduction-cleavage method.

  DOI：

  10.1021/jm00155a024
• 作为产物：
  描述：

  3-allyl-6-chloro-7,8-dimethoxy-1-(4-methoxyphenyl)2,3,4,5-tetrahydro-1H-3-benzazepine 、 甲烷磺酸 、 三溴化硼 以89%的产率得到
  参考文献：
  名称：

  ROSS, S. T.;FRANZ, R. G.;WILSON, J. W.;BRENNER, M.;DEMARINIS, R. M.;HIEBL+, J. MED. CHEM., 1986, 29, N 5, 733-740

  摘要：

  DOI：