N1-(4-methoxy)benzyl biguanide hydrochloride | 4767-41-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N1-(4-methoxy)benzyl biguanide hydrochloride
• 英文别名: 1-(4-methoxybenzyl)biguanide hydrochloride；1-(p-methoxybenzyl)biguanide hydrochloride；N1-(4-methoxybenzyl)-biguanide hydrochloride；1-(p-Methoxybenzyl)biguanide monohydrochloride；1-(diaminomethylidene)-2-[(4-methoxyphenyl)methyl]guanidine;hydrochloride
• CAS: 4767-41-3
• 化学式: C₁₀H₁₅N₅O*ClH
• 分子量: 257.723
• InChiKey: BMBCLCJJQXVDBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.21
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  112
• 氢给体数：
  4
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N1-(4-methoxy)benzyl biguanide hydrochloride 以85%的产率得到
  参考文献：
  名称：

  AROYAN A. A.; OVSEPYAN T. R.; AKOPYAN P. R.; PETROSYAN A. S., V SB. CZHNTEZY GETEROTSIKL. SOEDINENIJ. BZHP. 10. EREVAN, 1975, 7-9

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苄胺 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 N1-(4-methoxy)benzyl biguanide hydrochloride
  参考文献：
  名称：

  Synthesis and antimicrobial activity of N1-benzyl or N1-benzyloxy-1,6-dihydro-1,3,5-triazine-2,4-diamines

  摘要：

  The emergence and spread of multidrug-resistant strains of Staphylococcus aureus and Mycobacterium tuberculosis are generating a threat to public health worldwide. In the current study, a series of N-1-benzyl and N-1-benzyloxy-1,6-dihydro-1,3,5-triazine-2,4-diamine derivatives were synthesized and investigated for their antimicrobial activity against S. aureus, and Mycobacterium smegmatis which is taxonomically related to M. tuberculosis. Most of the compounds exhibited good activity against M. smegmatis as determined by comparison of diameters of the zone of inhibition of test compounds and standard antibiotics. Compound 7o showed potent antimycobacterial activity against M. smegmatis without mammalian DHFR inhibition liability. The results from this study indicate that 1-benzyl derivatives of 1,6-dihydro-1,3,5-triazine-2,4-diamines may be used as lead compounds for the discovery of antimycobacterial agents. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.125

文献信息

• Incorporation of a Biguanide Scaffold Enhances Drug Uptake by Organic Cation Transporters 1 and 2
  作者：Obinna N. Obianom、Ana L. Coutinho、Wei Yang、Hong Yang、Fengtian Xue、Yan Shu

  DOI：10.1021/acs.molpharmaceut.7b00285

  日期：2017.8.7

  Membrane transporters play a significant role in the transport of many endogenous and exogenous compounds. The knowledge of transporter substrate requirements has allowed further development of drugs that utilize them to ensure tissue permeation. In this study, we demonstrate that inclusion of a biguanide functionality can potentiate uptake by the organic cation transporters 1 and 2 (OCT1 and OCT2)

  膜转运蛋白在许多内源性和外源性化合物的转运中起着重要作用。转运蛋白底物要求的知识允许进一步开发利用它们来确保组织渗透的药物。在这项研究中，我们证明了包含双胍类功能可以增强有机阳离子转运蛋白1和2（OCT1和OCT2）的吸收。我们合成了18对结构上不同的化合物，每对均由母体氨基化合物及其双胍类似物组成；然后评估它们在过量表达人OCT1或OCT2的HEK293细胞中的细胞摄取。我们的结果表明，对于大多数化合物，双胍的添加显着改善了OCT1和OCT2介导的转运。双胍类也抑制了两种转运蛋白的原型底物的摄取，+）和二甲双胍。我们发现分子量，分子体积，Log D（pH 7.4）和可及表面积是OCT2底物的重要决定因素，但这些参数都不是OCT1的重要因素。更重要的是，两种细胞系中被测试的双胍类药物对MPP +摄取的抑制作用与二甲双胍的摄取抑制作用呈线性相关。两者合计，我们得出的结论是，在OCT1和OCT
• Synthesis and in vitro evaluation of 2,4-diamino-1,3,5-triazine derivatives as neuronal voltage-gated sodium channel blockers
  作者：Xiang Ma、Thong-Yuen Poon、Peter Tsun Hon Wong、Wai-Keung Chui

  DOI：10.1016/j.bmcl.2009.08.052

  日期：2009.10

  the best neuronal sodium binding activity among the four groups of triazines evaluated. Derivatives 4a–4j blocked the sodium channels with IC50 values ranged from 4.0 to 14.7 μM. The result from this study showed that analogues of 2,4-diamino-1,3,5-triazines could be used as leads for the discovery of neuronal sodium channels blockers for managing central nervous system related disorders.

  神经元钠通道阻滞剂会干扰离子通量，并已用于治疗神经性疼痛，癫痫和脑缺血性疾病。在目前的研究中，合成了四组2,4-二氨基-1,3,5-三嗪衍生物，并研究了它们的神经元钠通道结合活性。在四组三嗪中，发现5-Aryl-1,3,5-triazaspiro [5.5] undeca-1,3-diene-2,4-diamines（4a - 4j）具有最佳的神经元钠结合活性。衍生物4a – 4j用IC 50阻断了钠通道值范围为4.0至14.7μM。这项研究的结果表明，2,4-二氨基-1,3,5-三嗪的类似物可以用作发现神经元钠通道阻滞剂以治疗中枢神经系统相关疾病的先导。
• Novel biguanide-based derivatives scouted as TAAR1 agonists: Synthesis, biological evaluation, ADME prediction and molecular docking studies
  作者：Michele Tonelli、Stefano Espinoza、Raul R. Gainetdinov、Elena Cichero

  DOI：10.1016/j.ejmech.2016.10.058

  日期：2017.2

  murine and human TAAR1 agonists with potencies in nanomolar or low micromolar range, respectively. In particular, compounds BIG2 and BIG12-BIG14 were the most promising and they could be considered valuable lead compounds worthy of further investigations. In addition to the interest for developing more effective human TAAR1 ligands, the disclosed here potent murine TAAR1 agonists could offer suitable

  痕量胺（TAs）是内源性神经调节剂，在中枢神经系统（CNS）内的突触传递中起功能性作用，靶向痕量胺相关受体（TAARs）。从我们先前对TAAR1和TAAR5与非选择性配体3-碘胸腺嘧啶（T1AM）相互作用的计算研究开始，我们研究了27种基于双胍的衍生物在鼠和人TAAR1和鼠TAAR5受体上的功能活性，其中包括六种新合成的化合物。发现苯基（BIG2，BIG4，BIG8和BIG22）或苄基（BIG10-BIG16）双胍是选择性鼠类和人类TAAR1激动剂，分别具有纳米摩尔或低微摩尔范围的效力。特别是，化合物BIG2和BIG12-BIG14是最有前途的，可以认为它们是有价值的铅化合物，值得进一步研究。除了对开发更有效的人TAAR1配体的兴趣外，本文公开的强效鼠TAAR1激动剂还可以为研究TAAR1受体的药理学提供合适的工具。
• Novel 2,4-diamino-1,3,5-triazine derivative
  申请人：Maeda Shirou

  公开号：US20060154928A1

  公开（公告）日：2006-07-13

  The present invention relates to an antibacterial agent, which comprises, as an active ingredient, a compound represented by the following general formula (1): or a pharmaceutically acceptable salt thereof.

  本发明涉及一种抗菌剂，其包含以下通式（1）所表示的化合物作为活性成分，或其药学上可接受的盐。
• 2,4-diamino-1,3,5-triazine derivatives
  申请人：Hamari Chemicals, Ltd.

  公开号：US07622469B2

  公开（公告）日：2009-11-24

  The present invention relates to an antibacterial agent, which comprises, as an active ingredient, a compound represented by the following general formula (1): or a pharmaceutically acceptable salt thereof.

  本发明涉及一种抗菌剂，其包括以下通式（1）所表示的化合物或其药学上可接受的盐作为活性成分：