4-(4-Methylpiperazin-1-yl)-1-benzothiophene-2-carboxylic acid | 709044-37-1

• 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: 4-(4-Methylpiperazin-1-yl)-1-benzothiophene-2-carboxylic acid
• CAS: 709044-37-1
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: JFPPNVGECYOWKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-硝基苯乙胺 、 4-(4-Methylpiperazin-1-yl)-1-benzothiophene-2-carboxylic acid 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成
  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：

  2-氟-6-(4-甲基哌嗪-1-基)苯甲醛 在 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-(4-Methylpiperazin-1-yl)-1-benzothiophene-2-carboxylic acid
  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

• [EN] ARYLATION OF ALIPHATIC AMINES<br/>[FR] ARYLATION D'AMINES ALIPHATIQUES
  申请人：AAA CHEMISTRY APS

  公开号：WO2017137047A1

  公开（公告）日：2017-08-17

  The invention relates to a method for arylation of amines, such as aliphatic amines by reaction of aryl-halogens, e.g. chloro- or fluorobenzene derivatives without strongly electron withdrawing substituents in the presence of a strong base.

  这项发明涉及一种方法，用于通过芳基卤代烃（例如氯苯或氟苯衍生物）与强碱在场的情况下对胺进行芳基化，例如脂肪族胺。
• ARYLATION OF ALIPHATIC AMINES
  申请人：AAA Chemistry ApS

  公开号：EP3414216A1

  公开（公告）日：2018-12-19
• [EN] NOVEL HETEROAROMATIC PIPERAZINES FOR USE AS DRUGS<br/>[FR] NOUVELLES PIPERAZINES HETEROAROMATIQUES UTILES COMME MEDICAMENTS
  申请人：PIERRE FABRE MEDICAMENT

  公开号：WO1996041802A1

  公开（公告）日：1996-12-27

  (EN) Novel piperazines derived from 1-hetero-indenes, a method for preparing same, pharmaceutical or therapeutical compositions containing such compounds, and their use as drugs, are disclosed.(FR) La présente invention se rapporte à de nouvelles pipérazines dérivées des 1-hétéro-indènes, ainsi qu'à leur procédé de préparation, les compositions pharmaceutiques ou thérapeutiques les contenant et leur utilisation comme médicaments.