ethyl 4-(4-phenethyl-1-piperazinyl)benzo[b]thiophene-2-carboxylate | 159943-50-7

• 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: ethyl 4-(4-phenethyl-1-piperazinyl)benzo[b]thiophene-2-carboxylate
• 英文别名: Ethyl 4-[4-(2-phenylethyl)piperazin-1-yl]-1-benzothiophene-2-carboxylate
• CAS: 159943-50-7
• 化学式: C₂₃H₂₆N₂O₂S
• 分子量: 394.538
• InChiKey: DEQPJLZHHKPHFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-phenethyl-1-piperazinyl)benzo[b]thiophene-2-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 生成 4-(N-2-phenethylpiperazino)-1-benzo[b]thiophene-2-carboxylic acid hydrochloride
  参考文献：
  名称：

  Synthesis and serotonergic activity of variously substituted (3-amido)phenylpiperazine derivatives and benzothiophene-4-piperazine derivatives: novel antagonists for the vascular 5-HT1B receptor

  摘要：

  The synthesis and vascular 5-HT1B receptor activity of a novel series of substituted 3-amido phenylpiperazine and 4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene derivatives is described. Modifications to the amido linked sidechains of the 3-amidophenyl-piperazine derivatives and to the 2-sidechain of the 1-benzo[b]thiophene derivatives have been explored. Several compounds were identified which exhibited affinity at the vascular 5-HT1B receptor of pK(B) > 7.0. From the 3-aminophenyl-piperazine series, N-(4-(4-chlorophenyl)thiazol-2-yl-3-(4-methyl-1-piperazinyl)benzamide (30) and from the benzo[b]thiophene-4-piperazine series N-(2-ethylphenyl)-4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene-2-carboxamide (38) were identified as a highly potent, silent (as judged by the inability of angiotensin II to unmask 5-HT1B receptor mediated agonist activity in the rabbit femoral artery) and competitive vascular 5-HT1B receptor antagonist. The affinity of compounds from these two series of compounds for the vascular 5-HT1B receptor is discussed as well as a proposed mode of binding to the receptor pharmacophore. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.008
• 作为产物：
  描述：

  巯基乙酸乙酯 、 2-fluoro-6-(4-phenethyl-1-piperazinyl)benzaldehyde 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以60.6%的产率得到ethyl 4-(4-phenethyl-1-piperazinyl)benzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis and serotonergic activity of variously substituted (3-amido)phenylpiperazine derivatives and benzothiophene-4-piperazine derivatives: novel antagonists for the vascular 5-HT1B receptor

  摘要：

  The synthesis and vascular 5-HT1B receptor activity of a novel series of substituted 3-amido phenylpiperazine and 4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene derivatives is described. Modifications to the amido linked sidechains of the 3-amidophenyl-piperazine derivatives and to the 2-sidechain of the 1-benzo[b]thiophene derivatives have been explored. Several compounds were identified which exhibited affinity at the vascular 5-HT1B receptor of pK(B) > 7.0. From the 3-aminophenyl-piperazine series, N-(4-(4-chlorophenyl)thiazol-2-yl-3-(4-methyl-1-piperazinyl)benzamide (30) and from the benzo[b]thiophene-4-piperazine series N-(2-ethylphenyl)-4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene-2-carboxamide (38) were identified as a highly potent, silent (as judged by the inability of angiotensin II to unmask 5-HT1B receptor mediated agonist activity in the rabbit femoral artery) and competitive vascular 5-HT1B receptor antagonist. The affinity of compounds from these two series of compounds for the vascular 5-HT1B receptor is discussed as well as a proposed mode of binding to the receptor pharmacophore. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.12.008

文献信息

• SEROTONIN RECEPTOR AGENTS
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0660832B1

  公开（公告）日：1998-01-14
• US5436246A
  申请人：——

  公开号：US5436246A

  公开（公告）日：1995-07-25
• [EN] SEROTONIN RECEPTOR AGENTS<br/>[FR] AGENTS RECEPTEURS DE SEROTONINE
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：WO1994006789A1

  公开（公告）日：1994-03-31

  (EN) The present invention is directed to a new class of 2-optionnally substituted-4-piperazine-benzothiophene derivatives that are serotonin 5HT1A and 5HT1D receptor agents.(FR) L'invention concerne une nouvelle classe de dérivés de 2-éventuellement substitué-4-pipérazine-benzothiophène qui sont des agents récepteurs de sérotonine 5HT1A et 5HT1D.
• Synthesis and serotonergic activity of variously substituted (3-amido)phenylpiperazine derivatives and benzothiophene-4-piperazine derivatives: novel antagonists for the vascular 5-HT1B receptor
  作者：Gerard P. Moloney、Agatha Garavelas、Graeme R. Martin、Miles Maxwell、Robert C. Glen

  DOI：10.1016/j.ejmech.2003.12.008

  日期：2004.4

  The synthesis and vascular 5-HT1B receptor activity of a novel series of substituted 3-amido phenylpiperazine and 4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene derivatives is described. Modifications to the amido linked sidechains of the 3-amidophenyl-piperazine derivatives and to the 2-sidechain of the 1-benzo[b]thiophene derivatives have been explored. Several compounds were identified which exhibited affinity at the vascular 5-HT1B receptor of pK(B) > 7.0. From the 3-aminophenyl-piperazine series, N-(4-(4-chlorophenyl)thiazol-2-yl-3-(4-methyl-1-piperazinyl)benzamide (30) and from the benzo[b]thiophene-4-piperazine series N-(2-ethylphenyl)-4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene-2-carboxamide (38) were identified as a highly potent, silent (as judged by the inability of angiotensin II to unmask 5-HT1B receptor mediated agonist activity in the rabbit femoral artery) and competitive vascular 5-HT1B receptor antagonist. The affinity of compounds from these two series of compounds for the vascular 5-HT1B receptor is discussed as well as a proposed mode of binding to the receptor pharmacophore. (C) 2004 Elsevier SAS. All rights reserved.