1-(cyclohexylsulfonyl)piperazine | 1183873-04-2

• 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-(cyclohexylsulfonyl)piperazine
• 英文别名: 1-cyclohexylsulfonylpiperazine
• CAS: 1183873-04-2
• 化学式: C₁₀H₂₀N₂O₂S
• 分子量: 232.347
• InChiKey: AYMKHHUHNCVVNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  利尿酸 、 1-(cyclohexylsulfonyl)piperazine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83 mg的产率得到1-(2,3-dichloro-4-(2-(4-(cyclohexylsulfonyl)piperazin-1-yl)-2-oxoethoxy)phenyl)-2-methylenebutan-1-one
  参考文献：
  名称：

  具有磺酰胺作为有效抗癌剂的乙炔酸衍生物的合成和生物学评估。

  摘要：

  一系列的乙炔酸（2- [2,3-二氯-4-（2-亚甲基亚丁基丁酰基）苯氧基]乙酸）（EA，Edecrin），含有通过三种类型的接头连接的磺酰胺，即1,2-乙二胺，哌嗪和4合成β-氨基哌啶，随后在体外针对HL60和HCT116癌细胞系进行评估。除6a和6c外，所有EA类似物均具有抗增殖活性，IC 50s处于微摩尔范围（小于4 uM）。三个导数6b，7b和7e选择它们在HL60细胞系中具有有趣的双重活性，以便进一步针对一组癌细胞系（HCT116，A549，MCF7，PC3，U87-MG和SKOV3）以及在作为正常细胞系的MRC5上进行评估。这些化合物显示出针对A549，MCF7，PC3和HCT116细胞系的纳摩尔浓度的IC 50值，从而得出以下发现：哌嗪或4-氨基哌啶是开发具有高达24 nM的强抗增殖活性的EA类似物的最佳选择。。此外，就选择性而言，那些接头更适合提供高达63.8的安全系数。

  DOI：

  10.1016/j.bmcl.2020.127426
• 作为产物：
  描述：

  4-Cyclohexanesulfonyl-piperazine-1-carboxylic acid tert-butyl ester 生成 1-(cyclohexylsulfonyl)piperazine
  参考文献：
  名称：

  2,5-Disubstituted pyridines as potent GPR119 agonists

  摘要：

  A series of 2-piperazinyl-5-alkoxypyridines were synthesized and screened against human GPR119 receptor. Through SAR analysis, compounds containing 2-alkylsulfonylpiperazinyl-5-alkoxypyridines were discovered and found to be potent agonists of the human GPR119 receptor. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.083

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）。
• ARYLMETHOXY ISOINDOLINE DERIVATIVES AND COMPOSITIONS COMPRISING AND METHODS OF USING THE SAME
  申请人：Celgene Corporation

  公开号：US20180037567A1

  公开（公告）日：2018-02-08

  Provided are 4′-arylmethoxy isoindoline compounds, and pharmaceutically acceptable salts, solvates, clathrates, stereoisomers, and prodrugs thereof. Methods of use, and pharmaceutical compositions of these compounds are disclosed.

  提供了4'-芳基甲氧基异吲哚啉化合物及其药学上可接受的盐、溶剂合物、笼合物、立体异构体和前药。公开了这些化合物的使用方法和药物组合物。
• 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：
• 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.
• TG2 INHIBITOR COMPOUNDS AND USES THEREOF
  申请人：University Of Ottawa

  公开号：EP3442533A1

  公开（公告）日：2019-02-20