1-(1-benzo[b]thien-2-ylcarbonyl)piperazine | 1058149-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-(1-benzo[b]thien-2-ylcarbonyl)piperazine
• 英文别名: benzo[b]thiophen-2-yl-piperazin-1-yl-methanone；1-(1-Benzothiophene-2-carbonyl)piperazine；1-benzothiophen-2-yl(piperazin-1-yl)methanone
• CAS: 1058149-42-0
• 化学式: C₁₃H₁₄N₂OS
• 分子量: 246.333
• InChiKey: CVLWFBCLJOBFQT-UHFFFAOYSA-N

物化性质

• 沸点：
  443.1±35.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-benzo[b]thien-2-ylcarbonyl)piperazine 在 盐酸 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 (3R)-3-amino-1-[4-(1-benzothiophene-2-carbonyl)piperazin-1-yl]-4-(2,4,5-trifluorophenyl)butan-1-one
  参考文献：
  名称：

  Dipeptidyl peptidase-4 inhibitor with β-amino amide scaffold: Synthesis, SAR and biological evaluation

  摘要：

  Inhibitors of dipeptidyl peptidase-4 (DPP4) have been shown to be effective treatments for type 2 diabetes. Several series of beta-amino amide containing piperazine derivatives have been prepared and evaluated as a inhibitor of DPP4. Finally compound 5m was selected for further evaluation. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.019
• 作为产物：
  描述：

  苯并噻吩-2-羰酰氯 在 盐酸 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(1-benzo[b]thien-2-ylcarbonyl)piperazine
  参考文献：
  名称：

  Substituted phenoxypropyl-(R)-2-methylpyrrolidine aminomethyl ketones as histamine-3 receptor inverse agonists

  摘要：

  Optimization of a series of aminomethyl ketone diamine H3R antagonists to reduce the brain exposure by lowering the pKa, led to molecules with improved pharmacokinetic properties. Compounds 9, 19, and 25 had high affinity for human H3R and demonstrated in vivo H3R functional activity in the rat dipsogenia model. Compound 9 displayed modest wake-promoting activity in the rat EEG/EMG model. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.081

文献信息

• [EN] SUBSTITUTED PHENOXYPROPYLCYCLOAMINE DERIVATIVES AS HISTAMINE-3 (H3) RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS DE PHÉNOXYPROPYLCYCLOAMINE SUBSTITUÉS EN TANT QUE LIGANDS DE RÉCEPTEUR D'HISTAMINE-3 (H3)
  申请人：CEPHALON INC

  公开号：WO2011002984A1

  公开（公告）日：2011-01-06

  The present invention provides compounds of formula I: their use as H3 antagonists/inverse agonists, processes for their preparation, and pharmaceutical compositions thereof.

  本发明提供了式I的化合物：它们作为H3受体拮抗剂/逆向激动剂的用途，它们的制备方法以及药物组合物。
• Design, synthesis and biochemical evaluation of novel carbonic anhydrase inhibitors triggered by structural knowledge on hCA VII
  作者：Francesca Mancuso、Anna Di Fiore、Laura De Luca、Andrea Angeli、Giuseppina De Simone、Claudiu T. Supuran、Rosaria Gitto

  DOI：10.1016/j.bmc.2021.116279

  日期：2021.8

  To tackle the challenge of isoform selectivity, we explored the entrance of the cavity for selected druggable human Carbonic Anhydrases (hCAs). Based on X-ray crystallographic studies on the 4-(4-(2-chlorobenzoyl)piperazine-1-carbonyl)benzenesulfonamide in complex with the brain expressed hCA VII (PDB code: 7NC4), a series of 4-(4(hetero)aroylpiperazine-1-carbonyl)benzene-1-sulfonamides has been developed

  为了应对亚型选择性的挑战，我们探索了选定的可药物化人碳酸酐酶 (hCA) 的腔入口。基于 4-(4-(2-氯苯甲酰基)哌嗪-1-羰基)苯磺酰胺与脑表达的 hCA VII (PDB 代码：7NC4) 复合物的 X 射线晶体学研究，一系列 4-(4(杂已开发出)芳酰基哌嗪-1-羰基)苯-1-磺酰胺。为了评估其适合 hCA VII 催化腔的能力，通过对接模拟对新型苯磺酰胺进行了初步研究。然后，合成了这一系列 13 种苯磺酰胺，并针对选定的可成药 hCA 进行了测试。其中，与托吡酯（托吡酯）相比，4-(4-(呋喃-2-羰基)哌嗪-1-羰基)苯磺酰胺对 hCA VII ( K i : 4.3 nM) 表现出显着的亲和力，并且对生理上广泛存在的 hCA I 具有良好的选择性。 TPM）。
• Solvent-Free Microwave Synthesis of 3-(4-Benzo[b]thiophene-2-carbonyl)-1-piperazinyl-1-benzo[b]thiophen-2-yl-1-propanones. New Hetero Bis-Ligands with Potential 5-HT1A Serotonergic Activity
  作者：Hernán Pessoa-Mahana、Johann Kosche C.、Nadia Ron H.、Gonzalo Recabarren-Gajardo、Claudio Saitz B.、Ramiro Araya-Maturana、C. David Pessoa-Mahana

  DOI：10.3987/com-08-11326

  日期：——

  A novel series of 2-benzothiophenealkylpiperazine derivatives 11 (a-d) with potential affinity at 5-HT1A serotonin receptors have been synthesized via solvent-free, microwave-promoted Michael addition of benzo[b]thiophene piperazine derivatives 6(a-c) to substituted benzo[b]thiophen-2-yl propenones 10(b,c).
• SUBSTITUTED PHENOXYPROPYLCYCLOAMINE DERIVATIVES AS HISTAMINE-3 (H3) RECEPTOR LIGANDS
  申请人：Cephalon, Inc.

  公开号：EP2459529A1

  公开（公告）日：2012-06-06
• Substituted Phenoxypropylcycloamine Derivatives as Histamine-3 (H3) Receptor Ligands
  申请人：Bacon Edward R.

  公开号：US20120238551A1

  公开（公告）日：2012-09-20

  The present invention provides compounds of formula I: their use as H 3 antagonists/inverse agonists, processes for their preparation, and pharmaceutical compositions thereof.