4-甲基哌嗪-1-乙酰肼 | 24632-44-8

• 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: 4-甲基哌嗪-1-乙酰肼
• 中文别名: L-精氨酸单柠檬酸酯
• 英文名称: 4-methyl-1-piperazinylacetic acid hydrazide
• 英文别名: 2-(4-methylpiperazin-1-yl)acetohydrazide；2-(4-methylpiperazino)acethydrazide；(4-methyl-piperazin-1-yl)-acetic acid hydrazide；4-methylpiperazine-1-acetohydrazide；<4-Methyl-piperazino>-essigsaeure-hydrazid；1-Piperazineacetic acid, 4-methyl-, hydrazide
• CAS: 24632-44-8
• 化学式: C₇H₁₆N₄O
• 分子量: 172.23
• InChiKey: FNXGWGAOSHYTSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  61.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  4-甲基哌嗪-1-乙酰肼 在 diphenyl ether-biphenyl eutectic 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 生成 N,N-diethyl-5-(4-methyl-1-piperazinyl)-9-[(4-methyl-1-piperazinyl)methyl][1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamide
  参考文献：
  名称：

  1,8-Naphthyridines IX. Potent anti-inflammatory and/or analgesic activity of a new group of substituted 5-amino[1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides, of some their Mannich base derivatives and of one novel substituted 5-amino-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide derivative

  摘要：

  A new group of 5-(alkylamino)-9-isopropyl[1,2,4]triazolo[4,3-a][1,8]naphthyridine derivatives bearing a CONHR group at the 6-position (1c-g), designed to obtain new effective analgesic and/or anti-inflammatory agents, were synthesized and tested along with three new 9-alkyl-5-(4-alkyl-1-piperazinyl)-N,N-diethyl [1,2,4]triazolo[4,3-a][1,8]naphthyridine-6-carboxamides (2b-d). Besides, a new class of analogues of compounds 1 and 2, bearing a Mannich base moiety at the 9-position (12a-d), as well as the novel N,N-diethyl-5-(isobutylamino)-8-methyl-10-oxo-10H-pyrimido[1,2-a][1,8]naphthyridine-6-carboxamide (15) were prepared and tested. Compounds 1c-g exhibited very interesting anti-inflammatory properties in rats, whereas compounds 2b-d and 15 proved to be endowed with prevalent analgesic activity frequently associated with sedative effects in mice. On the contrary, the Mannich bases 12a-d resulted inactive. The most effective (80% inhibition of oedema) and potent (threshold dose 1.6 mg kg(-1) with 31% inhibition of oedema) anti-inflammatory compound 1d did not show gastrolesive effects following 100 mg kg(-1) oral administration in rats. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.069
• 作为产物：
  描述：

  N-甲基哌嗪 在 一水合肼 作用下， 以 乙醇 、 苯 为溶剂， 反应 13.0h， 生成 4-甲基哌嗪-1-乙酰肼
  参考文献：
  名称：

  Effect of a Procaspase-Activating Compound on the Catalytic Activity of Mature Caspase-3

  摘要：

  半胱天冬酶-3（Caspase-3）是一种具有二聚结构的凋亡执行酶，其酶原（procaspase-3）是利用合成化合物进行癌症化疗的靶蛋白。先前的研究表明，PAC-1（第一种促活化酶原的化合物）通过Zn2+螯合机制影响癌细胞中procaspase-3的激活。然而，我们发现该化合物在没有Zn2+的情况下也增强了成熟半胱天冬酶-3的活性。PAC-1对成熟半胱天冬酶-3活性的增强呈现出与化合物浓度相关的米哈利斯-门腾型饱和依赖性。PAC-1诱导了成熟半胱天冬酶-3的紫外-可见光谱的变化。根据这些发现，我们提出PAC-1与蛋白质核心之间存在直接的结构相互作用。根据PAC-1与成熟半胱天冬酶-3复合物的分子动力学计算，PAC-1可能结合于成熟半胱天冬酶-3二聚结构之间的界面。建议在PAC-1与影响成熟半胱天冬酶-3催化活性的氨基酸残基之间存在相互作用。在这项研究中，揭示了该促凋亡化合物的多种功能。

  DOI：

  10.1246/bcsj.20150139

文献信息

• Synthesis, biological activities and docking studies of piperazine incorporated 1, 3, 4-oxadiazole derivatives
  作者：Shipra Bhati、Vijay Kumar、Simranjeet Singh、Joginder Singh

  DOI：10.1016/j.molstruc.2019.04.106

  日期：2019.9

  Abstract New series of 1, 3, 4-oxadiazoles incorporating piperazine scaffolds in a single molecular framework has been reported. The structures of the synthesized derivatives were assigned by IR, NMR and mass spectral techniques. The hybrid compounds were evaluated for their antimicrobial, antitubercular and antioxidant activities. The observed MIC values of anti-tubular activities for the molecule

  摘要 新系列的 1, 3, 4-恶二唑在单分子框架中结合了哌嗪支架。通过红外、核磁共振和质谱技术确定了合成衍生物的结构。对杂化化合物的抗微生物、抗结核和抗氧化活性进行了评估。观察到的分子 3a、3b、3c、3d 和 3e 的抗肾小管活性的 MIC 值分别为 6.25、3.12、3.12、1.60 和 50.0 μg/ml。与抗坏血酸 (IC50 = 62.91 μg/ml) 相比，分子 3a 表现出更好的抗氧化活性 (IC50 = 36.72 μg/ml)。此外，所有分子都显示出显着的抗菌活性。此外，进行对接模拟以研究配体-蛋白质相互作用并确定可能的结合构象。在药物相似性模型研究中，化合物 3b 具有与标准药物链霉素相似的最大药物相似性模型评分 (0.75)。化合物 3a、3b 和 3c 是该系列中的潜在衍生物，可作为开发潜在治疗剂的先导化合物。
• Potential hypnotics and anxiolytics: 8-Chloro-6-(2-chlorophenyl)-1-[4-(2-methoxyethyl)piperazino]-methyl-4H-s-triazolo[4,3-a]-1,4-benzodiazepine and related compounds
  作者：Zdeněk Polívka、Jiří Holubek、Jan Metyš、Zdeněk Šedivý、Miroslav Protiva

  DOI：10.1135/cccc19833433

  日期：——

  Ethyl esters of 4-substituted piperazinoacetic acids IIIa-f were prepared by alkylation of 1-(ethoxycarbonylmethyl)piperazine with 2-methoxyethyl bromide, 2-ethoxyethyl bromide, 2-methylthioethyl chloride, 2-phenoxyethyl bromide and 2-phenylthioethyl bromide or by reactions of 1-(3-methoxypropyl)piperazine and 1-(2-methylthioethyl)piperazine with ethyl chloroacetate. Reactions of the esters with hydrazine hydrate gave the hydrazides IVa-f. Their treatment with 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-thione resulted in the title compound Ia and analogues Ib-f. 1-(4-Methylpiperazinomethyl) derivatives Ig and IIg were similarly prepared from 4-methylpiperazinoacetic acid hydrazide (IVg). Compound Ig showed significant central depressant and anticonvulsant (electroshock) activity in mice. The enlargement of the substituent in position 4 of the piperazine residue results in an important decrease of these activities.

  4-取代哌嗪基乙酸乙酯IIIa-f通过将1-(乙氧羰基甲基)哌嗪与2-甲氧基乙基溴、2-乙氧基乙基溴、2-甲硫基乙基氯化物、2-苯氧基乙基溴和2-苯硫基乙基溴进行烷基化反应制备，或者通过1-(3-甲氧基丙基)哌嗪和1-(2-甲硫基乙基)哌嗪与氯乙酸乙酯反应制备。这些酯与水合肼反应得到肼酰肼IVa-f。它们与7-氯-5-(2-氯苯基)-1,3-二氢-1,4-苯并二氮杂硫蒽-2-硫酮反应得到标题化合物Ia及类似物Ib-f。1-(4-甲基哌嗪基)衍生物Ig和IIg类似地由4-甲基哌嗪基乙酸肼IVg制备而成。化合物Ig在小鼠中显示出显著的中枢抑制和抗惊厥（电休克）活性。在哌嗪残基的4位上增大取代基会导致这些活性的显著减少。
• 1,6-Diazabicyclo [3,2,1] octan-7-one derivatives and their use in the treatment of bacterial infections
  申请人：Bhagwat Sachin

  公开号：US20140088068A1

  公开（公告）日：2014-03-27

  Compounds of Formula (I), their preparation and use in preventing or treating bacterial infections are disclosed.

  公式（I）化合物的制备和在预防或治疗细菌感染中的用途被披露。
• Dopamine-.beta.-hydroxylase inhibitors
  申请人：SmithKline Beckman Corporation

  公开号：US04761415A1

  公开（公告）日：1988-08-02

  Potent dopamine-.beta.-hydroxylase inhibitors having the Formula ##STR1## that are useful to inhibit dopamine-.beta.-hydroxylase activity, pharmaceutical compositions including these inhibitors, and methods of using these inhibitors to inhibit dopamine-.beta.-hydroxylase activity in mammals. Also disclosed are novel intermediates useful in preparing the presently invented inhibitors.

  具有式##STR1##的有效多巴胺-β-羟化酶抑制剂，可用于抑制哺乳动物中的多巴胺-β-羟化酶活性，包括这些抑制剂的制药组合物，以及使用这些抑制剂抑制哺乳动物中的多巴胺-β-羟化酶活性的方法。还披露了制备目前发明的抑制剂有用的新型中间体。
• Nitrogen containing heterocyclic compounds
  申请人：BHAGWAT Sachin

  公开号：US20140288064A1

  公开（公告）日：2014-09-25

  Compounds of Formula (I), their preparation and use in preventing or treating bacterial infections are disclosed.

  本发明公开了化学式（I）的化合物，其制备以及在预防或治疗细菌感染方面的用途。