1-(4-methoxybenzyl)guanidine hemisulfate | 21244-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-methoxybenzyl)guanidine hemisulfate
• 英文别名: 4-methoxybenzylguanidine sulfate；(4-methoxy-benzyl)-guanidine; sulfate；(4-Methoxy-benzyl)-guanidin; Sulfat；2-[(4-methoxyphenyl)methyl]guanidine;sulfuric acid
• CAS: 21244-39-3
• 化学式: 2C₉H₁₃N₃O*H₂O₄S
• 分子量: 456.523
• InChiKey: YFEWJSUXDZEOCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyl)guanidine hemisulfate 在 sodium amide 、 苯 作用下， 生成 松齐拉敏
  参考文献：
  名称：

  Saijo, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 1447,1450

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 镍 氨 作用下， 以 甲醇 、 水 为溶剂， 120.0 ℃ 、11.15 MPa 条件下， 反应 2.0h， 生成 1-(4-methoxybenzyl)guanidine hemisulfate
  参考文献：
  名称：

  Ovsepyan, T. R.; Akopyan, P. R.; Safrazbekyan, R. R., Pharmaceutical Chemistry Journal, 1998, vol. 32, # 12, p. 641 - 643

  摘要：

  DOI：

文献信息

• Second‐Generation Meridianin Analogues Inhibit the Formation of <i>Mycobacterium smegmatis</i> Biofilms and Sensitize Polymyxin‐Resistant Gram‐Negative Bacteria to Colistin
  作者：Michael J. Zeiler、Roberta J. Melander、Christian Melander

  DOI：10.1002/cmdc.202000438

  日期：2020.9.3

  problem is that antibiotics once seen as last‐resort drugs, such as the polymyxin colistin, are now seeing more frequent usage as resistance to front‐line drugs in Gram‐negative bacteria becomes more prevalent. The increased use of such antibiotics inevitably leads to an increased frequency of resistance. Drugs that inhibit biofilms and/or act as adjuvants to overcome resistance to existing antibiotics

  耐药细菌正迅速成为全球的一个重大问题。导致这场危机的一个因素是细菌生物膜在某些感染对常规抗生素效果的抵抗中所起的作用。生物膜内的细菌对抗生素治疗和宿主免疫反应都具有高度耐受性。生物膜与许多慢性感染有关，包括肺结核，在这些感染中它们可以充当细菌储库，需要采用艰难的抗生素方案来根除感染。一个单独的、复杂的问题是，曾经被视为最后手段的抗生素，如多粘菌素粘菌素，现在越来越频繁地使用，因为革兰氏阴性菌对一线药物的耐药性变得更加普遍。此类抗生素使用的增加不可避免地导致耐药性频率的增加。抑制生物膜和/或作为佐剂克服现有抗生素耐药性的药物可能成为未来抗菌治疗方法的重要组成部分。我们之前已经证明经络素天然产物家族的类似物具有佐剂和抗生物膜活性。在这项研究中，我们探索了先前研究中先导分子的结构变化，并确定了显示出改善的生物膜抑制效力和与粘菌素协同作用的化合物。我们之前已经证明经络素天然产物家族的类似物具有佐剂
• Investigation of new 2-aryl substituted Benzothiopyrano[4,3-d]pyrimidines as kinase inhibitors targeting vascular endothelial growth factor receptor 2
  作者：Silvia Salerno、Anna Maria Marini、Giacomo Fornaciari、Francesca Simorini、Concettina La Motta、Sabrina Taliani、Stefania Sartini、Federico Da Settimo、Aída Nelly García-Argáez、Ornella Gia、Sandro Cosconati、Ettore Novellino、Pilar D'Ocon、Anna Fioravanti、Paola Orlandi、Guido Bocci、Lisa Dalla Via

  DOI：10.1016/j.ejmech.2015.08.027

  日期：2015.10

  Vascular Endothelial Growth Factor (VEGF) pathway has emerged as one of the most important positive modulators of Angiogenesis, a central process implicated in tumour growth and metastatic dissemination. This led to the design and development of anti-VEGF monoclonal antibodies and small-molecule ATP-competitive VEGFR-inhibitors. In this study, we describe the synthesis and the biological evaluation of novel 2-aryl substituted benzothiopyrano-fused pyrimidines 1a-i, 2a-i and 3a-i. The ability of the compounds to target the VEGF pathway was determined in vitro exploiting the compounds' anti-proliferative efficacy against HUVEC cells. The VEGFR-2 inhibition was confirmed by enzymatic assays on recombinant human kinase insert domain receptor (KDR), by cell-based phospho-VEGFR-2 inhibition assays, and by ex vivo rat aortic ring tests. The selectivity profile of the best performing derivatives belonging to series 2 was further explored combining modeling studies and additional assays in a panel of human cell lines and other kinases. (C) 2015 Published by Elsevier Masson SAS.
• Discovery of Pyrido[3′,2′:5,6]thiopyrano[4,3-<i>d</i>]pyrimidine-Based Antiproliferative Multikinase Inhibitors
  作者：Silvia Salerno、Elisabetta Barresi、Aída Nelly García-Argáez、Sabrina Taliani、Francesca Simorini、Giorgio Amendola、Stefano Tomassi、Sandro Cosconati、Ettore Novellino、Federico Da Settimo、Anna Maria Marini、Lisa Dalla Via

  DOI：10.1021/acsmedchemlett.8b00499

  日期：2019.4.11

  Protein kinases dysregulation is extremely common in cancer cells, and the development of new agents able to simultaneously target multiple kinase pathways involved in angiogenesis and tumor growth may offer several advantages in the treatment of cancer. Herein we report the discovery of new pyridothiopyranopyrimidine derivatives (2-4) showing high potencies in VEGFR-2 KDR inhibition as well as antiproliferative effect on a panel of human tumor cell lines. Investigation on the selectivity profile of the representative 2-anilino-substituted compounds 3b, 3i, and 3j revealed a multiplicity of kinase targets that should account for the potent antiproliferative effect produced by these pyridothiopyranopyrimidine derivatives.
• Benzylguanidines and Other Galegine Analogues Inducing Weight Loss in Mice
  作者：Geoffrey D. Coxon、Brian L. Furman、Alan L. Harvey、John McTavish、Mark H. Mooney、Mahmoud Arastoo、Alan R. Kennedy、Justice M. Tettey、Roger D. Waigh

  DOI：10.1021/jm8011933

  日期：2009.6.11

  Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; +/- SEM) of -19.7 +/- 1.0, -11.0 +/- 0.7, and -7.3 +/- 0.8 in BALB/c, ob/ob, and DIO models, respectively.
• Direct Guanidinylation of Aryl and Heteroaryl Halides via Copper-Catalyzed Cross-Coupling Reaction
  作者：Hassan Hammoud、Martine Schmitt、Frédéric Bihel、Cyril Antheaume、Jean-Jacques Bourguignon

  DOI：10.1021/jo202018w

  日期：2012.1.6

  A modified Ullmann reaction using p-methoxybenzyl (PMB) guanidine as guanidinylation agent yielded various aryl and heteroaryl guanidines in good yields.