N-(2-氯-苄基)-胍 | 4406-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-氯-苄基)-胍
• 英文名称: 1-(2-chlorobenzyl)guanidine
• 英文别名: <2-Chlor-benzyl>-guanidin；2-Guanidinomethyl-1-chlor-benzol；N-(2-Chlorbenzyl)guanidin；(2-Chlor-benzyl)-guanidin；2-[(2-chlorophenyl)methyl]guanidine
• CAS: 4406-27-3
• 化学式: C₈H₁₀ClN₃
• 分子量: 183.64
• InChiKey: AKIBCPLFOPWWPF-UHFFFAOYSA-N

物化性质

• 沸点：
  301.7±44.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  (1H-imidazol-1-yl)(3,5,6-trimethylpyrazin-2-yl)methanone 、 N-(2-氯-苄基)-胍 反应 5.0h， 以28.9%的产率得到N-(N-(2-chlorobenzyl)carbamimidoyl)-3,5,6-trimethylpyrazine-2-carboxamide
  参考文献：
  名称：

  Ligustrazine Derivatives. Part 6: Design, Synthesis and Evaluation of Novel Ligustrazinyl Acylguanidine Derivatives as Potential Cardiovascular Agents

  摘要：

  A series of novel Ligustrazinyl acylguanidines was designed, synthesized and evaluated for their protective effect on injured vascular endothelial cell (ECV-304). The preliminary results demonstrated that some compounds possessed more potent activities than that of Ligustrazine in stimulating replication of the injured endothelial cell. Among the active compounds, compounds 8b, 8f and 8l displayed remarkable antioxidative activity with low EC50 values of 0.097, 0.059 and 0.094 mM, respectively. Structure-activity relationships were briefly discussed.

  DOI：

  10.2174/157340612802084243
• 作为产物：
  描述：

  1-(2-氯苄基)胍亚硫酸盐 在 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 N-(2-氯-苄基)-胍
  参考文献：
  名称：

  Ligustrazine Derivatives. Part 6: Design, Synthesis and Evaluation of Novel Ligustrazinyl Acylguanidine Derivatives as Potential Cardiovascular Agents

  摘要：

  A series of novel Ligustrazinyl acylguanidines was designed, synthesized and evaluated for their protective effect on injured vascular endothelial cell (ECV-304). The preliminary results demonstrated that some compounds possessed more potent activities than that of Ligustrazine in stimulating replication of the injured endothelial cell. Among the active compounds, compounds 8b, 8f and 8l displayed remarkable antioxidative activity with low EC50 values of 0.097, 0.059 and 0.094 mM, respectively. Structure-activity relationships were briefly discussed.

  DOI：

  10.2174/157340612802084243

文献信息

• [EN] GUANIDINE COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSÉS DE GUANIDINE ET LEUR UTILISATION
  申请人：HANALL BIOPHARMA CO LTD

  公开号：WO2015160220A1

  公开（公告）日：2015-10-22

  The present invention relates to guanidine compounds for inhibiting mitochondrial oxidative phosphorylation (OXPHOS) and use thereof. More specifically, the present invention relates to a pharmaceutical composition for preventing or treating a OXPHOS-related disease, particularly cancer by inhibiting mitochondrial oxidative phosphorylation and reprogramming cellular metabolism.

  本发明涉及用于抑制线粒体氧化磷酸化（OXPHOS）的胍啉化合物及其使用。更具体地，本发明涉及一种用于预防或治疗与OXPHOS相关的疾病，特别是通过抑制线粒体氧化磷酸化和重编程细胞代谢的药物组合物。
• Antimicrobial Activity of a Library of Thioxanthones and Their Potential as Efflux Pump Inhibitors
  作者：Fernando Durães、Andreia Palmeira、Bárbara Cruz、Joana Freitas-Silva、Nikoletta Szemerédi、Luís Gales、Paulo Martins da Costa、Fernando Remião、Renata Silva、Madalena Pinto、Gabriella Spengler、Emília Sousa

  DOI：10.3390/ph14060572

  日期：——

  design and synthesis of a library of thioxanthones as potential efflux pump inhibitors are described. The thioxanthone derivatives were investigated for their antibacterial activity and inhibition of efflux pumps, biofilm formation, and quorum-sensing. The compounds were also studied for their potential to interact with P-glycoprotein (P-gp, ABCB1), an efflux pump present in mammalian cells, and for

  外排泵的过度表达是引起多药耐药的原因之一，导致药物无效。这在抗菌素耐药性中起着举足轻重的作用，最显着的泵是 AcrAB-TolC 系统（AcrB 属于耐药性结节分裂家族）和来自主要促进剂超家族的 NorA。在细菌中，这些结构也有利于毒力和适应机制，例如群体感应和生物膜的形成。在这项研究中，描述了作为潜在外排泵抑制剂的噻吨酮库的设计和合成。对噻吨酮衍生物的抗菌活性和外排泵抑制、生物膜形成和群体感应进行了研究。还研究了这些化合物与 P-糖蛋白（P-gp，ABCB1）相互作用的潜力，存在于哺乳动物细胞中的外排泵，以及它们在小鼠成纤维细胞和人 Caco-2 细胞中的细胞毒性。关于实时溴化乙锭积累的结果可能表明潜在的细菌外排泵抑制作用，尚未报道噻吨酮。此外，人体细胞的体外研究表明，Caco-2 细胞中浓度高达 20 µM 时缺乏细胞毒性，一些衍生物也显示出 P-gp 调节的潜力。
• Tetracyclic Thioxanthene Derivatives: Studies on Fluorescence and Antitumor Activity
  作者：Fernando Durães、Patrícia M. A. Silva、Pedro Novais、Isabel Amorim、Luís Gales、Cátia I. C. Esteves、Samuel Guieu、Hassan Bousbaa、Madalena Pinto、Emília Sousa

  DOI：10.3390/molecules26113315

  日期：——

  unexpectedly, four tetracyclic thioxanthenes with a quinazoline–chromene scaffold were obtained. These compounds were studied for their human tumor cell growth inhibition activity, in the cell lines A375-C5, MCF-7 and NCI-H460. Photophysical studies were also performed. Two of the compounds displayed GI50 values below 10 µM for the three tested cell lines, and structure–activity relationship studies were established

  硫杂蒽酮是天然存在的氧杂蒽酮的生物等排体。它们被描述为具有多种活性，包括抗肿瘤。因此，人们继续合成噻吨酮库，但出人意料的是，获得了四个带有喹唑啉-色烯支架的四环噻吨酮。研究了这些化合物在细胞系 A375-C5、MCF-7 和 NCI-H460 中的人肿瘤细胞生长抑制活性。还进行了光物理研究。其中两种化合物显示出 GI 50三个测试细胞系的值低于 10 µM，并建立了结构-活性关系研究。三种化合物呈现出相似的吸收和发射波长，这是具有推拉特性的染料的特征。两种化合物的结构通过 X 射线晶体学进行了阐明。两种四环噻吨作为命中化合物出现。通过荧光显微镜和流式细胞术分析，这两种化合物之一在绿色通道中作为明亮的荧光染料在细胞内积累，使其成为有希望的治疗诊断癌症药物候选者。
• [EN] WEIGHT REDUCING COMPOUNDS<br/>[FR] COMPOSÉS DE RÉDUCTION DU POIDS
  申请人：UNIV STRATHCLYDE

  公开号：WO2009087395A1

  公开（公告）日：2009-07-16

  The present invention relates to compounds which find use as weight reducing agents, and find use in treating obesity and/or excess adiposity.

  本发明涉及一种化合物，可用作减重剂，并可用于治疗肥胖和/或过多的脂肪堆积。
• Rational Design of a Novel Class of Human ClpP Agonists through a Ring-Opening Strategy with Enhanced Antileukemia Activity
  作者：Xinrong Xiang、Zhengyi Dai、Baozhu Luo、Ninglin Zhao、Song Liu、Jing Sui、Jiasheng Huang、Yuanzheng Zhou、Jinlong Gu、Jiangnan Zhang、Tao Yang、Rui Bao、Youfu Luo

  DOI：10.1021/acs.jmedchem.4c00338

  日期：2024.4.25

  agonist imipridone ONC201. Here, a novel class of HsClpP agonists is designed and synthesized using a ring-opening strategy based on the lead compound 1 reported in our previous study. Among these novel scaffold agonists, compound 7k exhibited remarkably enhanced proteolytic activity of HsClpP (EC50 = 0.79 ± 0.03 μM) and antitumor activity in vitro (IC50 = 0.038 ± 0.003 μM). Moreover, the intraperitoneal

  通过化学或遗传策略激活智人酪蛋白裂解蛋白酶 P (HsClpP) 已被证明是治疗急性髓系白血病 (AML) 的一种新的潜在疗法。然而，经典激动剂咪啶酮ONC201的疗效有限。在此，基于我们之前研究中报道的先导化合物1 ，使用开环策略设计并合成了一类新型 HsClpP 激动剂。在这些新型支架激动剂中，化合物7k表现出显着增强的HsClpP蛋白水解活性（EC 50 = 0.79 ± 0.03 μM）和体外抗肿瘤活性（IC 50 = 0.038 ± 0.003 μM）。此外，腹腔注射化合物7k可显着抑制Mv4-11异种移植模型中的肿瘤生长，肿瘤生长抑制率达到88%。同时， 7k在体内表现出有利的药代动力学特性。这项研究强调了化合物7k作为重要的 HsClpP 激动剂和抗白血病候选药物的前景，值得进一步探索 AML 治疗。