1-(3-pyridyl)sulfonylpiperazine | 26103-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(3-pyridyl)sulfonylpiperazine
• 英文别名: Pyridin-3-sulonsaeure-piperazid；1-(pyridin-3-ylsulfonyl)piperazine；1-(pyridine-3-sulfonyl)-piperazine；1-(Pyridine-3-sulfonyl)piperazine；1-pyridin-3-ylsulfonylpiperazine
• CAS: 26103-50-4
• 化学式: C₉H₁₃N₃O₂S
• mdl: MFCD09743152
• 分子量: 227.287
• InChiKey: IJCSWJUPKXRQBR-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：
  0.444
• 拓扑面积：
  70.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-pyridyl)sulfonylpiperazine 在 溶剂黄146 、 1-丙基磷酸酐 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成
  参考文献：
  名称：

  Identification of a small chemical as a lysosomal calcium mobilizer and characterization of its ability to inhibit autophagy and viral infection

  摘要：

  我们之前发现甘油醛-3-磷酸脱氢酶（GAPDH）是环磷酸腺苷（cADPR）的结合蛋白之一，并发现 GAPDH 通过雷诺丁受体（RyRs）参与了 cADPR 介导的内质网 Ca2+ 释放。在此，我们旨在化学合成新型 cADPR 类似物并对其进行药理学表征。根据模拟的 cADPR-GAPDH 复合物结构，我们进行了基于结构的药物筛选，确定了几种与 GAPDH 中的 cADPR 结合口袋对接得分较高的小分子化学物质，并证明其中的两种化合物 C244 和 C346 是潜在的 cADPR 拮抗剂。我们进一步合成了 C346 的几种类似物，发现其类似物 G42 也能动员溶酶体释放 Ca2+。G42 可碱化溶酶体 pH 值并抑制自噬体-溶酶体融合。此外，G42 还能明显抑制寨卡病毒（ZIKV，一种黄病毒）或小鼠肝炎病毒（MHV，一种β-冠状病毒）对宿主细胞的感染。这些结果表明，G42 可能通过引发溶酶体 Ca2+ 动员和抑制自噬来抑制病毒感染。

  DOI：

  10.1111/febs.16920
• 作为产物：
  描述：

  tert-butyl 4-(pyridin-3-ylsulfonyl)piperazine-1-carboxylate 生成 1-(3-pyridyl)sulfonylpiperazine
  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

• Synthesis and antibacterial activity of novel myricetin derivatives containing sulfonylpiperazine
  作者：Jun He、Xue-Mei Tang、Ting-Ting Liu、Feng Peng、Qing Zhou、Li-Wei Liu、Ming He、Wei Xue

  DOI：10.1007/s11696-020-01363-3

  日期：2021.3

  Myricetin derivatives containing sulfonylpiperazine were synthesized and their structures were confirmed by NMR and HRMS. The antibacterial activity results indicated that some compounds showed good antibacterial activity against Xanthomonas oryzaepv. oryzae (Xoo), Xanthomonas axonopodispv. citri (Xac) and Ralstonia solanacearum (Rs). Among them, compounds 4m and 4p revealed excellent antibacterial activities

  合成了含有磺酰基哌嗪的杨梅素衍生物，并通过NMR和HRMS证实其结构。抗菌活性结果表明，某些化合物对米生黄单胞菌具有良好的抗菌活性。米（Xoo），黄单胞菌（Xanthomonas axonopodispv）。柠檬（Xac）和青枯菌（Rsstonia solanacearum）（Rs）。其中，化合物4m和4p对Rs表现出优异的抗菌活性，其浓度为最大作用浓度的50％（EC 50）值分别为4和4μg/ mL，优于对照药物比美噻唑（13μg/ mL）和硫二唑铜（185μg/ mL）。如使用扫描电子显微镜（SEM）所观察到的，这些化合物通过引起细菌表面的折叠和变形而起作用，从而导致细菌结构不完整，从而达到抑菌的目的。合成的杨梅素衍生物有望指导新型抗菌剂的研究方向。
• 一种含磺酰基哌嗪的杨梅素衍生物、制备方法及用途
  申请人：贵州大学

  公开号：CN112209910A

  公开（公告）日：2021-01-12

  本发明公开了一种含磺酰基哌嗪的杨梅素衍生物、制备方法及用途，其结构通式如下所示：其中，R为取代苯基、取代芳杂环基；n为碳链中碳的个数分别为3、4。取代苯基为苯环上邻、间、对位含有一个或一个以上的C1‑6的烷基、C1‑6的烷氧基、硝基、卤素原子。取代芳杂环基为噻吩基、呋喃基、吡咯基、吡啶基等，芳杂环上的取代基为邻、间、对位含有一个或一个以上的C1‑6的烷基、C1‑6的烷氧基、硝基、卤素原子。本发明对抑植物病菌有较好的防治效果，可作为农用杀菌剂。
• Structure–Activity Relationship Studies of Sulfonylpiperazine Analogues as Novel Negative Allosteric Modulators of Human Neuronal Nicotinic Receptors
  作者：Brandon J. Henderson、Daniel J. Carper、Tatiana F. González-Cestari、Bitna Yi、Kiran Mahasenan、Ryan E. Pavlovicz、Martin L. Dalefield、Robert S. Coleman、Chenglong Li、Dennis B. McKay

  DOI：10.1021/jm201294r

  日期：2011.12.22

  Neuronal nicotinic receptors have been implicated in several diseases and disorders such as autism, Alzheimer's disease, Parkinson's disease, epilepsy, and various forms of addiction. To understand the role of nicotinic receptors in these conditions, it would be beneficial to have selective molecules that target specific nicotinic receptors in vitro and in vivo. Our laboratory has previously identified novel negative allosteric modulators of human alpha 4 beta 2 (H alpha 4 beta 2) and human alpha 3 beta 4 (H alpha 3 beta 4) nicotinic receptors. The effects of novel sulfonylpiperazine analogues that act as negative allosteric modulators on both H alpha 4 beta 2 nAChRs and H alpha 3 beta 4 nAChRs were investigated. This work, through structure activity relationship (SAR) studies, describes the chemical features of these molecules that are important for both potency and selectivity on H alpha 4 beta 2 nAChRs.
• 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.