1-(benzylsulfonyl)piperazine | 186412-62-4

• 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: 1-(benzylsulfonyl)piperazine
• 英文别名: N-benzylsulfonylpiperazine；1-benzylsulfonylpiperazine
• CAS: 186412-62-4
• 化学式: C₁₁H₁₆N₂O₂S
• mdl: MFCD03444529
• 分子量: 240.326
• InChiKey: FXLVCHSCGBTGPL-UHFFFAOYSA-N

物化性质

• 沸点：
  402.8±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-金刚烷甲酸 、 1-(benzylsulfonyl)piperazine 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(Adamantane-1-carbonyl)-4-phenylmethanesulfonylpiperazine
  参考文献：
  名称：

  Discovery and biological evaluation of adamantyl amide 11β-HSD1 inhibitors

  摘要：

  A series of adamantyl amide 11 beta-HSD1 inhibitors has been discovered and chemically modified. Selected compounds are selective for 11 beta-HSD1 over 11 beta-HSD2 and possess excellent cellular potency in human and murine 11 beta-HSD1 assays. Good pharmacodynamic characteristics are observed in ex vivo assays. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.057
• 作为产物：
  描述：

  tert-butyl 4-(benzylsulfonyl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-(benzylsulfonyl)piperazine
  参考文献：
  名称：

  Novel Compounds

  摘要：

  这项发明涉及用作治疗呼吸系统疾病的有用药用化合物的取代芳基酸，包含它们的药用组合物以及它们的制备过程。

  公开号：

  US20080255150A1

文献信息

• [EN] TG2 INHIBITOR COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS INHIBITEURS DE TG2 ET UTILISATIONS DE CES DERNIERS
  申请人：UNIV OTTAWA

  公开号：WO2017179018A1

  公开（公告）日：2017-10-19

  There are provided Tissue Transglutaminase (TG2) inhibitor compounds, and compositions and methods of use thereof for the prevention or treatment of a cancer. Compounds of Formula I, and pharmaceutically acceptable salts thereof, are provided: Formula (I).

  提供了组织转谷氨酰胺酶（TG2）抑制剂化合物，以及其用于预防或治疗癌症的组合物和使用方法。提供了化合物I的公式，以及其药用盐：公式（I）。
• Benzimidazolinones, benzoxazolinones, benzopiperazinones, indanones, and derivatives thereof as inhibitors of factor Xa
  申请人：——

  公开号：US20010021775A1

  公开（公告）日：2001-09-13

  The present application describes inhibitors of factor Xa of formula I: 1 or pharmaceutically acceptable salt forms thereof, wherein W, W 1 , W 2 , and W 3 may be N or C and J, j a , and j b combine to form a substituted carbocycle or heterocycle.

  本申请描述了公式I的因子Xa抑制剂：1或其药学上可接受的盐形式，其中W，W1，W2和W3可能是N或C，J，ja和jb结合形成取代的碳环或杂环。
• TG2 inhibitor piperazine compounds and uses thereof
  申请人：UNIVERSITY OF OTTAWA

  公开号：US10894777B2

  公开（公告）日：2021-01-19

  There are provided Tissue Transglutaminase (TG2) inhibitor compounds, and compositions and methods of use thereof for the prevention or treatment of a cancer. Compounds of Formula I, and pharmaceutically acceptable salts thereof, are provided:

  提供了组织转谷氨酰胺酶（TG2）抑制剂化合物及其用于预防或治疗癌症的组合物和使用方法。提供了式 I 的化合物及其药学上可接受的盐类：
• 10.1016/j.bioorg.2024.107762
  作者：Ma, Bingjing、Li, Hua、Huang, Yuan、Guo, Yaming、Xu, Caizhu、Li, Wei

  DOI：10.1016/j.bioorg.2024.107762

  日期：——

  immune responses, which indicate that specific inhibition of JAK-STAT pathway would be a potential key strategy for RA (Rheumatoid arthritis) treatment. Cedrol (CE), found from ginger by our group earlier, has been proven to play an excellent role in ameliorating RA via acting on JAK3. In this study, 27 new (, –), along with one known () derivatives of CE were synthesized by using chloroacetic acid and

  JAK-STAT信号通路被认为在炎症性疾病和免疫反应的调节中发挥重要作用，这表明特异性抑制JAK-STAT通路将成为RA（类风湿性关节炎）治疗的潜在关键策略。本课题组前期从生姜中发现的雪松醇（CE）已被证明通过作用于JAK3对改善RA具有良好的作用。在这项研究中，使用氯乙酸和丙烯酰氯作为中间配体合成了 27 种新的 (, –) 以及一种已知的 () CE 衍生物。采用HTRF（均质时间分辨荧光）检测技术进行对JAK激酶的抑制效果，比传统方法更加方便、稳定。该结果与LPS诱导的p-JAK3的分泌相比，更能反映化合物真正的激酶选择性作用。该化合物被确定为一种有效的抑制剂，可以以剂量依赖性方式减少 LPS 诱导的 p-JAK3 的分泌。鉴于这些结果，该化合物可以作为 JAK3 的有利抑制剂进行进一步研究。
• Structure–Activity Relationships of Potent, Targeted Covalent Inhibitors That Abolish Both the Transamidation and GTP Binding Activities of Human Tissue Transglutaminase
  作者：Abdullah Akbar、Nicole M. R. McNeil、Marie R. Albert、Viviane Ta、Gautam Adhikary、Karine Bourgeois、Richard L. Eckert、Jeffrey W. Keillor

  DOI：10.1021/acs.jmedchem.7b01070

  日期：2017.9.28

  Human tissue transglutaminase (hTG2) is a multifunctional enzyme. It is primarily known for its calcium dependent transamidation activity that leads to formation of an isopeptide bond between glutamine and lysine residues found on the surface of proteins, but it is also a GTP binding protein. Overexpression and unregulated hTG2 activity have been associated with numerous human diseases, including cancer stem cell survival and metastatic phenotype. Herein, we present a series of targeted covalent inhibitors (TCIs) based on our previously reported Cbz-Lys scaffold. From this structure activity relationship (SAR) study, novel irreversible inhibitors were identified that block the transamidation activity of hTG2 and allosterically abolish its GTP binding ability with a high degree of selectivity and efficiency (k(inact)/K-I > 10(5) M-1 min(-1)). One optimized inhibitor (VA4) was also shown to inhibit epidermal cancer stem cell invasion with an EC50 of 3.9 mu M, representing a significant improvement over our previously reported "hit" NC9.