1-(丁烷-1-磺酰基)-哌嗪 | 926206-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(丁烷-1-磺酰基)-哌嗪
• 英文名称: 1-(butylsulfonyl)piperazine
• 英文别名: 1-butylsulfonylpiperazine
• CAS: 926206-14-6
• 化学式: C₈H₁₈N₂O₂S
• mdl: MFCD08442234
• 分子量: 206.309
• InChiKey: GHWABFFIFVLMOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  322.9±52.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• 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：

  1-(丁烷-1-磺酰基)-哌嗪 在 N-甲基吗啉 、 吡啶 、 TEA 、 硫化氢 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 89.0h， 生成 3-[3-[4-(Butane-1-sulfonyl)-piperazin-1-yl]-2-(naphthalene-2-sulfonylamino)-3-oxo-propyl]-thiobenzimidic acid methyl ester; hydriodide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Potent Thrombin Inhibitors:  Piperazides of 3-Amidinophenylalanine

  摘要：

  Thrombin is the key enzyme in the blood coagulation system, and inhibitors of its proteolytic activity are of therapeutic interest since they are potential anticoagulants. The most potent inhibitor of the benzamidine type is N-alpha-[(2-naphthylsulfonyl)glycyl]-4-amidinophenylalanylpiperidide (NAPAP). However, NAPAP and other benzamidine derivatives do not show favorable pharmacological properties; above all, they have very low systemic bioavailability after oral administration. The goal of designing new compounds was to obtain potent inhibitors with improved pharmacokinetic properties. Piperazide derivatives of 3-amidinophenylalanine as the key building block were synthesized. The piperazine moiety opened the possibility to introduce quite different substituents on the second nitrogen using common synthetic procedures. Some of the newly synthesized compounds are potent inhibitors of thrombin and offer an approach to study structure-function relationships for inhibition of thrombin and related enzymes and for the improvement of their pharmacokinetic properties.

  DOI：

  10.1021/jm960668h
• 作为产物：
  描述：

  Tert-butyl 4-butylsulfonylpiperazine-1-carboxylate 生成 1-(丁烷-1-磺酰基)-哌嗪
  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

• Thienopyrimidines useful as modulators of ion channels
  申请人：Fanning T.D. Lev

  公开号：US20070287717A1

  公开（公告）日：2007-12-13

  The present invention relates to compounds useful as inhibitors of ion channels. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及作为离子通道抑制剂有用的化合物。该发明还提供了包含本发明化合物的药学上可接受的组合物，以及使用这些组合物治疗各种疾病的方法。
• Development of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates bearing sulfonylpiperazine as antitumor inhibitors targeting PI3Kα
  作者：Yong Yin、Shao Sha、Xun Wu、She-Feng Wang、Fang Qiao、Zhong-Cheng Song、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2019.111630

  日期：2019.11

  PI3K signal pathway plays a vital role in cellular functions and becomes an attractive approach for cancer therapy. Herein, a new series of novel chromeno[4,3-c]pyrazol-4(2H)-one derivatives bearing sulfonylpiperazine based on the PI3K inhibitors and our previous research. They were screened for their PI3K inhibitory activities and anticancer effects in vitro. Biological studies indicated that compound 7m revealed the remarkable antiproliferative activity (IC50 ranging from 0.03 to 0.09 mu M) against four cancer cell lines (A549, Huh7, HL60 and HCT-116). Besides, compound 7m displayed a certain selective for PI3K alpha (IC50 = 0.009 mu M) over PI3K beta, gamma and delta, and meanwhile, it can remarkable decreased the expression level of p-Akt (Ser473) and p-S6K. In addition, compound 7m could not only induce HCT-116 cell arrest at G1 phase in a dose-dependent manner, but also induce cell apoptosis via upregulation of Bax and cleaved-caspase 3/9, and downregulation of Bcl-2. Besides, compound 7m can remarkably inhibit the growth of tumor in vivo. The above results suggested that compound 7m could be considered as a promising PI3K alpha inhibitor. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and potent cytotoxic activity of novel 7-( N -[(substituted-sulfonyl)piperazinyl]-methyl)-camptothecin derivatives
  作者：Gao-Xiang Zhu、Pi-Le Cheng、Masuo Goto、Na Zhang、Susan L. Morris-Natschke、Kan-Yen Hsieh、Guan-Zhou Yang、Qian-Ru Yang、Ying-Qian Liu、Hai-Le Chen、Xiao-Shuai Zhang、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2017.02.066

  日期：2017.4

  In an effort to discover potent camptothecin-derived antitumor agents, novel camptothecin analogues with sulfonylpiperazinyl motifs at position-7 were designed and synthesized. They were evaluated for in vitro cytotoxicity with the sulforhodamine-B (SRB) method in five types of human tumor cell lines, A-549, MDA-MB-231, KB, KB-VIN and MCF-7. With IC50 values in the low mu M to nM level, most of the new analogues showed greater cytotoxicity activity than the reference compounds irinotecan and topotecan. Furthermore, compounds 121 (IC50, 1.2 nM) and 12k (IC50, 20.2 nM) displayed the highest cytotoxicity against the multidrug-resistant (MDR) KB-VIN cell line and merit further development as preclinical drug candidates for treating cancer, including MDR phenotype. Our study suggested that integration of sulfonylpiperazinyl motifs into position-7 of camptothecin is an effective strategy for discovering new potent cytotoxic camptothecin derivatives. (C) 2017 Elsevier Ltd. All rights reserved.
• Design, synthesis, and biological evaluation of quinolinedione-linked sulfonylpiperazine derivatives as NQO1-directed antitumor agents
  作者：Kerong Guo、Jian Li、Yingdong Jia、Xiaojuan Yang、Xiqing Yan、Liqiang Wu

  DOI：10.1016/j.bioorg.2023.106385

  日期：2023.3
• THIENOPYRIMIDINES USEFUL AS MODULATORS OF ION CHANNELS
  申请人：Vertex Pharmaceuticals, Inc.

  公开号：EP2043654A2

  公开（公告）日：2009-04-08