2-[4-[2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]piperazin-1-yl]cyclohepta-2,4,6-trien-1-one | 80101-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-[4-[2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]piperazin-1-yl]cyclohepta-2,4,6-trien-1-one
• CAS: 80101-44-6
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: VYMZHZUGLSYBBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(1-piperazinyl)-2,4,6-cycloheptatrien-1-one methanesulfonic acid salt 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 26.0h， 生成 2-[4-[2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]piperazin-1-yl]cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Troponoids. 7. Chemistry and dopamine agaonist activity of ciladopa and related aralkyltroponylpiperazines

  摘要：

  A series of N-aralkyltroponylpiperazine derivatives were synthesized and evaluated for dopaminergic activity in rats rendered hypokinetic by the bilateral injection of 6-hydroxydopamine (6-OHDA) into the anterolateral hypothalamus. Several members of the series were active, and a structure-activity relationship is presented. A few selected compounds were also evaluated with regard to their ability to induce contralateral rotational behavior in rats with a unilateral 6-OHDA-induced lesion of the nigrostriatal dopamine (DA) pathway and to suppress elevated serum prolactin levels. The compounds were compared to bromocriptine. Some of the more potent analogues were also assayed for their binding affinity to dopamine (DA) and alpha 1-adrenergic receptors. The results established that the potency of some of the compounds were comparable or superior to that of bromocriptine indicated that potent dopaminergic activity was dependent on the presence of both a substituted phenyl and a troponylpiperazine moiety, and confirmed that the dopaminergic activity depends on relative and absolute stereochemistry.

  DOI：

  10.1021/jm00152a004

文献信息

• BAGLI, J.;BOGRI, T.;VOITH, K.;LEE, D., J. MED. CHEM., 1986, 29, N 2, 186-193
  作者：BAGLI, J.、BOGRI, T.、VOITH, K.、LEE, D.

  DOI：——

  日期：——
• US4469695A
  申请人：——

  公开号：US4469695A

  公开（公告）日：1984-09-04
• Troponoids. 7. Chemistry and dopamine agaonist activity of ciladopa and related aralkyltroponylpiperazines
  作者：Jehan Bagli、T. Bogri、Katherine Voith、D. Lee

  DOI：10.1021/jm00152a004

  日期：1986.2

  A series of N-aralkyltroponylpiperazine derivatives were synthesized and evaluated for dopaminergic activity in rats rendered hypokinetic by the bilateral injection of 6-hydroxydopamine (6-OHDA) into the anterolateral hypothalamus. Several members of the series were active, and a structure-activity relationship is presented. A few selected compounds were also evaluated with regard to their ability to induce contralateral rotational behavior in rats with a unilateral 6-OHDA-induced lesion of the nigrostriatal dopamine (DA) pathway and to suppress elevated serum prolactin levels. The compounds were compared to bromocriptine. Some of the more potent analogues were also assayed for their binding affinity to dopamine (DA) and alpha 1-adrenergic receptors. The results established that the potency of some of the compounds were comparable or superior to that of bromocriptine indicated that potent dopaminergic activity was dependent on the presence of both a substituted phenyl and a troponylpiperazine moiety, and confirmed that the dopaminergic activity depends on relative and absolute stereochemistry.