2-[4-(p-tolylsulfonyl)piperazin-1-yl]-1H-benzimidazole | 1209218-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-(p-tolylsulfonyl)piperazin-1-yl]-1H-benzimidazole
• 英文别名: 2-(4-tosylpiperazin-1-yl)benzo[d]imidazole；2-(4-tosylpiperazin-1-yl)-1H-benzo[d]imidazole；2-[4-(4-methylphenyl)sulfonylpiperazin-1-yl]-1H-benzimidazole
• CAS: 1209218-74-5
• 化学式: C₁₈H₂₀N₄O₂S
• 分子量: 356.448
• InChiKey: JWYRKYCSYIHSKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  77.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯苯并咪唑 在 氢溴酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 2-[4-(p-tolylsulfonyl)piperazin-1-yl]-1H-benzimidazole
  参考文献：
  名称：

  Synthesis and biological analysis of benzazol-2-yl piperazine sulfonamides as 11β-hydroxysteroid dehydrogenase 1 inhibitors

  摘要：

  In the last decade the inhibition of the enzyme 11 beta-hydroxysteroid dehydrogenase 1 (11 beta-HSD1) emerged as a promising new strategy to treat diabetes and several metabolic syndrome phenotypes. Using a molecular modeling approach and classical bioisosteric studies, we discovered a new class of 11 beta-HSD1 inhibitors bearing an arylsulfonylpiperazine scaffold. Optimization of the initial lead resulted in compound 11 that selectively inhibits 11 beta-HSD1 (IC50 = 0.7 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.07.047

文献信息

• Aqueous, One-Pot, Three-Component Reaction for Efficient Synthesis of 2-[4-(Arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, ‑1H-benzimidazole, or -1,3-benzoxazole Derivatives
  作者：Kommula Dileep、M. Murty

  DOI：10.1055/s-0036-1590972

  日期：2017.10

  A simple and efficient synthetic protocol has been developed involving a one-pot three-component reaction of a 2-chlorobenzazole, piperazine, and an arenesulfonyl chloride under aqueous conditions at room temperature in the absence of a catalyst, ligand, or base. By using this protocol, a variety of 2-[4-(arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, -1H-benzimidazole, and -1,3-benzoxazole derivatives

  已开发出一种简单有效的合成方案，涉及 2-氯苯并唑、哌嗪和芳烃磺酰氯在室温水性条件下在没有催化剂、配体或碱的情况下的一锅三组分反应。通过使用该协议, 以极好的收率合成了各种 2-[4-(芳基磺酰基)哌嗪-1-基]-1,3-苯并噻唑、-1H-苯并咪唑和-1,3-苯并恶唑衍生物。
• Synthesis and biological analysis of benzazol-2-yl piperazine sulfonamides as 11β-hydroxysteroid dehydrogenase 1 inhibitors
  作者：Sandra Hofer、Denise V. Kratschmar、Brigitte Schernthanner、Anna Vuorinen、Daniela Schuster、Alex Odermatt、Johnny Easmon

  DOI：10.1016/j.bmcl.2013.07.047

  日期：2013.10

  In the last decade the inhibition of the enzyme 11 beta-hydroxysteroid dehydrogenase 1 (11 beta-HSD1) emerged as a promising new strategy to treat diabetes and several metabolic syndrome phenotypes. Using a molecular modeling approach and classical bioisosteric studies, we discovered a new class of 11 beta-HSD1 inhibitors bearing an arylsulfonylpiperazine scaffold. Optimization of the initial lead resulted in compound 11 that selectively inhibits 11 beta-HSD1 (IC50 = 0.7 mu M). (C) 2013 Elsevier Ltd. All rights reserved.