4-methylpiperazin-1-yl-biguanidine dihydrochloride | 18413-26-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-methylpiperazin-1-yl-biguanidine dihydrochloride
• 英文别名: N¹-Methyl-N⁴-biguanidino-piperazin；1-(4-Methyl-piperazinyl-(1)-formimidoyl)-guanidin；N-carbamimidoyl-4-methyl-piperazine-1-carboximidic acid amide；(4-methyl-piperazine-1-carboximidoyl)-guanidine；N-(aminoiminomethyl)-4-methyl-1-piperazinecarboximidamide；(4-Methyl-piperazin-1-carbimidoyl)-guanidin；N-[amino(imino)methyl]-4-methylpiperazine-1-carboximidamide；N-(diaminomethylidene)-4-methylpiperazine-1-carboximidamide
• CAS: 18413-26-8
• 化学式: C₇H₁₆N₆
• mdl: MFCD15204029
• 分子量: 184.244
• InChiKey: ZGISTEMQWYSJHP-UHFFFAOYSA-N

物化性质

• 沸点：
  267.9±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  94.7
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methylpiperazin-1-yl-biguanidine dihydrochloride 、 咪唑并[1,2-A]吡嗪-2-甲酸乙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以31%的产率得到4-imidazo[1,2-a]pyrazin-2-yl-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine
  参考文献：
  名称：

  Synthesis and cardiotonic activity of 2,4-diamino-1.3,5-triazines

  摘要：

  DOI：

  10.1016/0223-5234(89)90171-2
• 作为产物：
  描述：

  N-甲基哌嗪 、 二聚氰胺 以 正丁醇 为溶剂， 反应 6.0h， 生成 4-methylpiperazin-1-yl-biguanidine dihydrochloride
  参考文献：
  名称：

  组胺H4受体亲和力的1,3,5-三嗪衍生物和JNJ7777120类似物的合成及其与PTEN启动子的相互作用

  摘要：

  最近已经使用H 4 R激动剂和拮抗剂研究了组胺和H 4受体（H 4 R）在癌症中的参与。该研究项目的范围是合成和探索一组具有组胺H 4受体（H 4 R）亲和力的化合物对编码抗肿瘤PTEN蛋白的PTEN基因启动子的影响。合成了一系列基于H 4 R拮抗剂JNJ7777120结构或1,3,5-三嗪支架的新型化合物，评估了其对组胺H 4 R的亲和力并用于本研究。化合物5和7属于该组的JNJ7777120类似物显示出与启动子的最高相互作用PTEN基因和弱亲和力针对ħ 4 R 2与ķ我值> 100 μ米。这些化合物对神经母细胞瘤IMR-32细胞的存活率没有显着影响，表明PTEN基因启动子亲和力和抗肿瘤活性之间没有相关性。化合物6，另一JNJ7777120类似物，显示出与计算出的IC上IMR-32活性的影响最高50 = 23.27 μ米。1,3,5-三嗪衍生物与PTEN的相互作用通常较低或中等基因启动子。但是，具有对溴取代基的1

  DOI：

  10.1111/cbdd.12752

文献信息

• Discovery of phenylselenoether-hydantoin hybrids as ABCB1 efflux pump modulating agents with cytotoxic and antiproliferative actions in resistant T-lymphoma
  作者：Wesam Ali、Gabriella Spengler、Annamária Kincses、Márta Nové、Cecilia Battistelli、Gniewomir Latacz、Małgorzata Starek、Monika Dąbrowska、Ewelina Honkisz-Orzechowska、Annalisa Romanelli、Manuela Monica Rasile、Ewa Szymańska、Claus Jacob、Clemens Zwergel、Jadwiga Handzlik

  DOI：10.1016/j.ejmech.2020.112435

  日期：2020.8

  terms of design, synthesis, and biological assays, including an insight into cellular mechanisms of anticancer action as well as an ADMET-screening in vitro were performed, followed by in-depth SAR analysis. Among the investigated new phenylselenoether hybrids, four compounds showed significant cytotoxic and anti-proliferative effects, in particular, in resistant cancer cells. Hydantoin derivatives (5–7)

  癌细胞中的多药耐药性（MDR）是成功治疗癌症要考虑的关键方面。P-gp / ABCB1是ABC转运蛋白的成员，参与了主要的肿瘤MDR机制，负责药物和细胞毒性物质的外排。在这里，我们描述了一种具有潜在抗癌活性的有效的含硒ABCB1 MDR外排泵调节剂的发现。对三组硒醚进行了设计，合成和生物学分析方面的全面研究，包括深入了解抗癌作用的细胞机制以及体外ADMET筛选进行了深入的SAR分析。在研究的新的苯基硒醚杂化物中，四种化合物表现出显着的细胞毒性和抗增殖作用，特别是在耐药性癌细胞中。乙内酰脲衍生物（5 – 7）比参考抑制剂维拉帕米（在低10倍的浓度下最高可达2.6倍）调节ABCB1外排泵的效果显着，并且还具有良好的药物相互作用曲线。最好的化合物（6在人的JURKAT T淋巴细胞癌细胞中进一步评估了其对细胞增殖速率的影响。从机制上讲，细胞周期增强剂cyclin D1的表达下降，而单独用化合物6或
• 3-deoxyglucosone and skin
  申请人：——

  公开号：US20030219440A1

  公开（公告）日：2003-11-27

  The invention relates to a method of removing 3-deoxyglucosone and other alpha-dicarbonyl sugars from skin. The invention further relates to methods of inhibiting production and function of 3-deoxyglucosone and other alpha-dicarbonyl sugars in skin. The invention also relates to methods of treating 3-deoxyglucosone and other alpha-dicarbonyl sugars associated diseases and disorders of skin.

  该发明涉及一种从皮肤中去除3-去氧葡萄糖酮和其他α-二酮糖的方法。该发明还涉及抑制皮肤中3-去氧葡萄糖酮和其他α-二酮糖的产生和功能的方法。该发明还涉及治疗与皮肤相关的3-去氧葡萄糖酮和其他α-二酮糖相关疾病和障碍的方法。
• Synthesis and<i> In Vitro</i> AMPK Activation of Cycloalkyl/Alkarylbiguanides with Robust<i> In Vivo</i> Antihyperglycemic Action
  作者：Erika Gutierrez-Lara、Carlos Martínez-Conde、Edgar Rosales-Ortega、Juan José Ramírez-Espinosa、Julio C. Rivera-Leyva、David Centurión、Karla Carvajal、Daniel Ortega-Cuellar、Samuel Estrada-Soto、Gabriel Navarrete-Vázquez

  DOI：10.1155/2017/1212609

  日期：——

  This work describes the design, synthesis in one step, and the in vitro, in vivo, and in silico antidiabetic evaluation of a series of ten alicyclic and aromatic (alkyl +aryl: alkaryl)biguanides, analogues of metformin and phenformin. The design was conceived using isosteric replacement, chain-ring transformation, and lower and higher homologation strategies. All compounds were obtained as crystals and their structure was confirmed on the basis of their spectral data (NMR and mass spectra), and their purity was ascertained by microanalysis. Compounds were in vitro evaluated as activators of AMP-Activated Protein Kinase (AMPK). The results indicated that compounds 4, 5, and 6 showed similar or even better effect compared to metformin. Docking analysis was performed with regulatory subunit γ of AMPK, showing several interactions with nucleotide binding pocket. The in vivo evaluation of compounds 4–6 at a single dose of 50 mg/kg was performed in a murine experimental model of diabetes. The results showed an important and robust decrease of plasmatic glucose levels (−40%). Compound 6 was selected for an oral glucose tolerance test, showing an antihyperglycemic effect similar to metformin. The in vivo results indicated that compounds 4–6 may be effective in treating experimental T2DM.

  这项工作描述了设计、一步合成以及一系列十种脂环和芳香（烷基+芳基：烷芳基）双胍类似物（与二甲双胍和苯乙双胍类似物）的体外、体内和体外抗糖尿病评价。设计是通过同位素替代、链环转化以及较低和较高同系物策略构思的。所有化合物均以晶体形式获得，并根据其光谱数据（NMR和质谱）确认了其结构，通过微量分析确定了其纯度。化合物在体外被评估为AMP激活蛋白激酶（AMPK）的激活剂。结果表明，化合物4、5和6与二甲双胍相比显示出类似或甚至更好的效果。使用AMPK的调节亚基γ进行对接分析，显示出与核苷酸结合口袋的多个相互作用。在小鼠糖尿病实验模型中，对化合物4-6进行了50mg/kg的单剂量体内评价。结果显示血浆葡萄糖水平显著下降（-40%）。选择化合物6进行口服葡萄糖耐量试验，显示出与二甲双胍类似的抗高血糖效果。体内结果表明，化合物4-6可能有效治疗实验性T2DM。
• Fructoseamine 3 kinase and the formation of collagen and elastin
  申请人：Tobia Annette

  公开号：US20070065443A1

  公开（公告）日：2007-03-22

  The invention relates to the discovery that levels of collagen and elastin can be modulated by changing the flux through the Amadori Pathway and that copper containing compounds and complexes inhibit the enzyme fructoseamine-3-kinase.

  本发明涉及到一项发现，即通过改变Amadori途径的通量可以调节胶原蛋白和弹性蛋白的水平，并且含铜化合物和配合物可以抑制酶果糖胺-3-激酶。
• Method for reducing a susceptibility to tumor formation induced by 3-deoxyglucosone and precursors thereof
  申请人：Brown R. Truman

  公开号：US20060089316A1

  公开（公告）日：2006-04-27

  Disclosed are methods of using various compounds, which are known to bind to 3-deoxyglucosone (3DG) or precursors thereof, in order to reduce a susceptibility to tumor formation and/or to prevent or delay onset of tumor formation induced by 3DG and its precursors. Also disclosed is the reduction of 3DG levels in high fructose corn syrop so that the high fructose corn syrup is less likely to induce tumor formation.

  公开了使用各种已知与3-脱氧葡萄糖酮（3DG）或其前体结合的化合物的方法，以减少对肿瘤形成的易感性和/或预防或延迟由3DG及其前体诱导的肿瘤形成。还公开了降低高果糖玉米糖浆中3DG水平的方法，以使高果糖玉米糖浆不太可能诱导肿瘤形成。