Ciladopa | 80101-33-3

• 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: Ciladopa
• 英文别名: 2-{4-[2-(3,4-Dimethoxyphenyl)-2-hydroxyethyl]piperazin-1-yl}cyclohepta-2,4,6-trien-1-one；2-[4-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]piperazin-1-yl]cyclohepta-2,4,6-trien-1-one
• CAS: 80101-33-3
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: SGEKLKJQLHJVDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ciladopa 生成 (2R,3R)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid;2-[4-[2-(3,4-dimethoxyphenyl)-2-hydroxyethyl]piperazin-1-yl]cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  BAGLI, J. F.;BOEGRI, T.;VOITH, K.

  摘要：

  DOI：
• 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 Ciladopa
  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

• 2-(4-Hydroxyalkyl-1-piperazinyl)-2,4,6-cycloheptatrien-1-one derivatives
  申请人：Ayerst, McKenna & Harrison, Inc.

  公开号：US04469695A1

  公开（公告）日：1984-09-04

  2-(4-Hydroxyalkyl-1-piperazinyl)-2,4,6-cycloheptatrien-1-one derivatives, therapeutically acceptable acid addition salts thereof, processes for their preparation, methods of using the derivatives and pharmaceutical compositions of the derivatives are disclosed. The derivatives exhibit dopamine-receptor stimulating activity in a mammal and are useful for treating hyperprolactinemia, galactorrhea, amenorrhea, impotence, Parkinsonism, diabetes, acromegaly, hypertension and other central nervous system disorders.

  本发明涉及2-(4-羟基烷基-1-哌嗪基)-2,4,6-环庚三烯-1-酮衍生物及其治疗上可接受的酸盐加成物，以及它们的制备方法、使用衍生物的方法和制备衍生物的药物组合物。该衍生物在哺乳动物中表现出多巴胺受体刺激活性，并且可用于治疗高泌乳素血症、分泌乳汁、闭经、阳痿、帕金森病、糖尿病、肢端肥大症、高血压和其他中枢神经系统疾病。
• 2-(1-Piperazinyl)-2,4,6-cycloheptatrien-1-one derivatives, processes for their preparation, intermediates used in the processes and the preparation thereof and pharmaceutical compositions containing the derivatives
  申请人：AYERST, MCKENNA AND HARRISON INC.

  公开号：EP0034894A2

  公开（公告）日：1981-09-02

  2-(1-Piperazinyl)-2,4,6-cycloheptatrien-1-one derivatives offormula and therapeutically acceptable acid addition salts thereof exhibit dopamine-receptor stimulating activity in a mammal and are useful for treating hyperprolactinemia, galactorrhea, amenorrhea, impotence, Parkinsonism, diabetes, acromegaly, hypertension and other central nervous system disorders. In the formula R is hydrogen or a specified substituent, R2 is hydrogen or lower alkyl and R3 is hydrogen or a specified radical. Processes for preparing the derivatives and pharmaceutical compositions containing them are also disclosed.

  2-(1-哌嗪基)-2,4,6-环庚三烯-1-酮衍生物 及其治疗上可接受的酸加成盐在哺乳动物体内具有刺激多巴胺受体的活性，可用于治疗高泌乳素血症、闭经、阳痿、帕金森病、糖尿病、肢端肥大症、高血压和其他中枢神经系统疾病。 式中 R 是氢或特定的取代基，R2 是氢或低级烷基，R3 是氢或特定的基。此外，还公开了制备这些衍生物和含有这些衍生物的药物组合物的工艺。
• A stereospecific microbial reduction
  申请人：AYERST, MCKENNA AND HARRISON INC.

  公开号：EP0148612A2

  公开（公告）日：1985-07-17

  The dopaminergic antagonist ciladopa, also known as S(-)-2-[4-[2-hydroxy-2-(3,4-dimethoxyphenyl)ethyl]-1-piperazinyl]-2,4,6-cycloheptatrien-1-one, is prepared by stereospecific microbial reduction of 2-[4-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-1-piperazinyl]-2,4,6-cycloheptatrien-1-one.

  多巴胺能拮抗剂西拉多巴（又称 S(-)-2-[4-[2-羟基-2-(3,4-二甲氧基苯基)乙基]-1-哌嗪基]-2,4,6-环庚三烯-1-酮）是通过立体特异性微生物还原 2-[4-[2-(3,4-二甲氧基苯基)-2-氧代乙基]-1-哌嗪基]-2,4,6-环庚三烯-1-酮制备而成的。
• BAGLI, J. F.;BOGRI, T.;VOIT, K.
  作者：BAGLI, J. F.、BOGRI, T.、VOIT, K.

  DOI：——

  日期：——
• BAGLI, J. F.;BOEGRI, T.;VOITH, K.
  作者：BAGLI, J. F.、BOEGRI, T.、VOITH, K.

  DOI：——

  日期：——