2,3,5-三甲基-6-(哌嗪-1-基甲基)吡嗪 | 892396-47-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2,3,5-三甲基-6-(哌嗪-1-基甲基)吡嗪
• 英文名称: 2,3,5-trimethyl-6-(piperazin-1-ylmethyl)pyrazine
• 英文别名: 2,3,5-Trimethyl-6-[(piperazin-1-yl)methyl]pyrazine
• CAS: 892396-47-3
• 化学式: C₁₂H₂₀N₄
• 分子量: 220.318
• InChiKey: LWIIGNGSOUSWCH-UHFFFAOYSA-N

物化性质

• 熔点：
  94 °C(Solv: hexane (110-54-3))
• 沸点：
  327.2±37.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  41
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,5-三甲基-6-(哌嗪-1-基甲基)吡嗪 、 2-(4-硝基苯基)乙酰氯 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以41%的产率得到2-[4-(4-nitrophenylacetyl)-1-piperazinomethyl]-3,5,6-trimethylpyrazine
  参考文献：
  名称：

  Ligustrazine derivatives. Part 3: Design, synthesis and evaluation of novel acylpiperazinyl derivatives as potential cerebrocardiac vascular agents

  摘要：

  A series of novel acylpiperazinyl Ligustrazine derivatives was designed, synthesized, and their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities were evaluated. The results showed that compound E33 displayed most potential protective effects on the ECV-304 cells damaged by hydrogen peroxide, and compound E1 was found to be the most active antiplatelet aggregation agent. Structure-activity relationships were briefly discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.012
• 作为产物：
  描述：

  (3,5,6-三甲基吡嗪-2-基)甲醇 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 2,3,5-三甲基-6-(哌嗪-1-基甲基)吡嗪
  参考文献：
  名称：

  一种京尼平衍生物、其制备方法及应用

  摘要：

  本发明公开了一种京尼平衍生物或其可药用盐，所述京尼平衍生物为式(Ia)或(Ib)所示的化合物：#imgabs0#。本发明具有较现有抑郁症临床用药氟西汀、京尼平更优的抗抑郁以及神经保护作用，且起效快，副作用小，临床应用前景广阔。

  公开号：

  CN117069686A

文献信息

• Discovery of talmapimod analogues as polypharmacological anti-inflammatory agents
  作者：Wandong Liu、Caiyun Hou、Jiaming Li、Xiaodong Ma、Yanchun Zhang、Mengqi Hu、Yuanzheng Huang

  DOI：10.1080/14756366.2019.1693703

  日期：2020.1.1

  Twenty novel talmapimod analogues were designed, synthesised and evaluated for the in vivo anti-inflammatory activities. Among them, compound 6n, the most potent one, was selected for exploring the mechanisms underlying its anti-inflammatory efficacy. In RAW264.7 cells, it effectively suppressed lipopolysaccharides-induced (LPS-induced) expressions of iNOS and COX-2. As illustrated by the western blot

  设计，合成和评估了二十种新的talmapimod类似物的体内抗炎活性。其中，选择最有效的化合物6n来探索其抗炎功效的潜在机制。在RAW264.7细胞中，它有效地抑制了脂多糖诱导的（LPS诱导的）iNOS和COX-2的表达。如蛋白质印迹分析所示，6n下调了NF-κB信号转导和p38 MAPK磷酸化。进一步的酶法分析确定6n是对p38αMAPK（IC50 = 1.95 µM）和COX-2（IC50 = 0.036 µM）的有效抑制剂。由于同时抑制p38αMAPK，其上游效应物和COX-2以及下调NF-κB和MAPK信号通路的能力6n（一种多药理抗炎剂），
• Design, synthesis, and evaluation of genipin derivatives for the treatment of Alzheimer's Disease
  作者：Weijun Huang、Yujun Wang、Jiaming Li、Yanchun Zhang、Xiaodong Ma、Panhu Zhu、Yang Zhang

  DOI：10.1111/cbdd.13194

  日期：2019.2

  derivatives have been designed, synthesized, and evaluated for their inhibitory activity against acetylcholinesterase (AChE). As a result, compound 13a bearing ligustrazine moiety displayed the most potent AChE inhibitory activity in this series with IC50 value of 218 nm. Besides, MTT assay was performed to investigate the neuroprotection of these compounds against PC12 cells injured by Amyloid β‐protein

  已经设计，合成并评估了22种新颖的Genipin衍生物对乙酰胆碱酯酶（AChE）的抑制活性。结果，带有川gust嗪部分的化合物13a在该系列中表现出最有效的AChE抑制活性，IC 50值为218 n m。此外，进行了MTT分析以研究这些化合物对淀粉样β蛋白1-42（Aβ1-42）损伤的PC12细胞的神经保护作用。其中8a的抑制率（％Inhibition = 22.29）比阳性对照多奈哌齐（％Inhibition = 17.65）高。
• Design, synthesis, biological evaluation and docking study of novel indole-2-amide as anti-inflammatory agents with dual inhibition of COX and 5-LOX
  作者：Yuanzheng Huang、Bin Zhang、Jiaming Li、Huicai Liu、Yanchun Zhang、Zhang Yang、Wandong Liu

  DOI：10.1016/j.ejmech.2019.07.004

  日期：2019.10

  In this work, a series of novel indole-2-amide compounds were designed, synthesized, characterized and the anti-inflammatory activity in vivo were evaluated. Compounds 8a, 10b, 12h, and 121 exhibited marked anti-inflammatory activity in 2,4-Dinitrofluorobenzenethe (DNFB) - induced mice auricle edema model. Further, compounds 8a, 10b and 12h exhibited potential in vitro COX-2 inhibitory activity (IC50 = 21.86, 233 and 23.21 nM, respectively), while the reference drug celecoxib was 11.20 nM. The most promising compound 10b was exhibited the highest selectivity for COX-2 (selectivity index (COX-1/COX-2) = 17.45) and moderate 5-LOX inhibitory activity (IC50 = 66 nM), which comparable to positive controlled zileuton (IC50 = 38.91 nM). In addition, the test results showed compounds 10b and 12h no significant cytotoxic activity on normal cells (RAW264.7). Further, at the active sites of the COX-1, COX-2 co crystals, 3b and 41 showed higher binding forces in the molecular docking study, which consistent with the results of in vitro experiments. These results demonstrated that these compounds had dual inhibitory activity of COX/5-LOX, providing clues for further searching for safer and more effective anti-inflammatory drugs. (C) 2019 Published by Elsevier Masson SAS.
• Design, synthesis, and biological activities of novel Ligustrazine derivatives
  作者：Xian-Chao Cheng、Xin-Yong Liu、Wen-Fang Xu、Xiu-Li Guo、Yang Ou

  DOI：10.1016/j.bmc.2007.03.033

  日期：2007.5

  A series of novel Ligustrazine derivatives was designed, synthesized, and assayed for their protective effects on damaged ECV-304 cells and antiplatelet aggregation activities. The results showed that most Ligustrazine derivatives exhibited lower EC50 values for protective effects on the ECV-304 cells damaged by hydrogen peroxide in comparison with Ligustrazine. And some Ligustrazine derivatives presented better antiplatelet aggregation activities than Ligustrazine. The derivatives containing the bisphenylmethyl pharmacophore (7a-c) exhibited highest potency. Compound 7a displayed most potential protective effects on the ECV-304 cells damaged by hydrogen peroxide, and compound 7c was found to be the most active antiplatelet aggregation agent. Structure-activity relationships were briefly discussed. (c) 2007 Elsevier Ltd. All rights reserved.
• Cheng, Xian-Chao; Liu, Xin-Yong; Xu, Wen-Fang, Journal of Chemical Research, 2006, # 9, p. 577 - 579
  作者：Cheng, Xian-Chao、Liu, Xin-Yong、Xu, Wen-Fang

  DOI：——

  日期：——