9-(4-aminobutyl)-9H-purin-6-amine | 182627-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(4-aminobutyl)-9H-purin-6-amine
• 英文别名: 9-(4-aminobutyl)adenine；9-(4-Amino-butyl)-6-amino-9H-purin；9-(4-amino-butyl)-9H-purin-6-ylamine；4-(6-amino-9H-purin-9-yl)-butylamine；9-(4-aminobutyl)purin-6-amine
• CAS: 182627-49-2
• 化学式: C₉H₁₄N₆
• 分子量: 206.25
• InChiKey: YEZGDZJDOXMCME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(4-aminobutyl)-9H-purin-6-amine 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 1-[4-(6-Amino-purin-9-yl)-butyl]-7-chloro-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  On the binding site of quinolone antibacterials. An attempt to probe the shen model

  摘要：

  Quinolone-nucleic acid base hybrids were synthesized in an effort to probe a mechanistic model and a proposed mode of antibacterial action where stacked pairs of quinolones interact with DNA through H-bonding. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00430-1
• 作为产物：
  描述：

  9-(4-氯丁基)嘌呤-6-胺 在 Ra-Ni sodium azide 、 四丁基溴化铵 、 氢气 作用下， 以 乙腈 为溶剂， 生成 9-(4-aminobutyl)-9H-purin-6-amine
  参考文献：
  名称：

  On the binding site of quinolone antibacterials. An attempt to probe the shen model

  摘要：

  Quinolone-nucleic acid base hybrids were synthesized in an effort to probe a mechanistic model and a proposed mode of antibacterial action where stacked pairs of quinolones interact with DNA through H-bonding. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00430-1

文献信息

• Antibacterial Agents
  申请人：Das Biswajit

  公开号：US20080318878A1

  公开（公告）日：2008-12-25

  The present invention provides acylide derivatives, which can be used as antibacterial agents. Compounds disclosed herein can be used for treating or preventing conditions caused by or contributed to by Gram-positive, Gram-negative or anaerobic bacteria, more particularly against, for example, Staphylococci, Streptococci, Enterococci, Haemophilus, Moraxalla spp., Chlamydia spp., Mycoplasm, Legionella spp., Mycobacterium, Helicobacter, Clostridium, Bacteroides, Corynebacterium, Bacillus, Enterobactericeae or any combination thereof. Also provided are processes for preparing compounds disclosed herein, pharmaceutical compositions thereof, and method of treating bacterial infections.

  本发明提供了酰亚胺衍生物，可用作抗菌剂。本文披露的化合物可用于治疗或预防由革兰氏阳性、革兰氏阴性或厌氧细菌引起或促成的疾病，更具体地针对例如葡萄球菌、链球菌、肠球菌、流感嗜血杆菌、嗜盐杆菌、沙眼衣原体、支原体、军团菌、分枝杆菌、幽门螺杆菌、梭菌、拟杆菌、棒状杆菌、肠杆菌科细菌或其任意组合。还提供了制备本文披露的化合物的方法、其药物组合物以及治疗细菌感染的方法。
• [EN] NOVEL ANTIBIOTIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS ANTIBIOTIQUES
  申请人：UNIV ADELAIDE

  公开号：WO2020087122A1

  公开（公告）日：2020-05-07

  Novel antimicrobial inhibitors of Biotin Protein Ligase (BPL), which incorporate biotin, are described. The inhibitors have a structure that inhibit the essential metabolic enzyme BPL of pathogens and have been shown to be stable in whole blood and effective at reducing BPL activity in acceptable concentrations. The described compounds have shown to be effective against, for example, Staphylococcus aureus and compare favourably against erythromycin

  描述了一种新型抗微生物生物素蛋白连接酶（BPL）抑制剂，其中包含生物素。这些抑制剂具有一种结构，可以抑制病原体的关键代谢酶BPL，并且已经证明在全血中稳定，并且在可接受的浓度下能有效降低BPL活性。所描述的化合物已被证明对金黄色葡萄球菌等病原体有效，并且与红霉素相比具有较好的效果。
• Dynamic Covalent Template-Guided Screen for Nucleic Acid-Targeting Agents
  作者：Sarah B. Krueger、Steven C. Zimmerman

  DOI：10.1021/acs.jmedchem.2c01086

  日期：2022.9.22

  Trinucleotide repeat diseases such as myotonic dystrophy type 1 (DM1) and Huntington’s disease (HD) are caused by expanded DNA repeats that can be used as templates to synthesize their own inhibitors. Because it would be particularly advantageous to reversibly assemble multivalent nucleic acid-targeting agents in situ, we sought to develop a target-guided screen that uses dynamic covalent chemistry

  三核苷酸重复疾病如 1 型强直性营养不良 (DM1) 和亨廷顿病 (HD) 是由扩增的 DNA 重复引起的，这些重复可用作合成它们自己的抑制剂的模板。因为原位可逆组装多价核酸靶向剂将是特别有利的，我们试图开发一种使用动态共价化学来识别多靶点抑制剂的靶点引导筛选。我们报告了含胺或醛的片段库的合成。这些片段的组装导致了一组多样化的命中组合，这些组合在存在 DM1 和 HD 重复序列的情况下通过基质辅助激光解吸/电离质谱 (MALDI-MS) 得到证实。对这两种疾病感兴趣的是，由此产生的命中组合在体外以合作方式选择性地抑制转录，抑制浓度 (IC 50 ) 值在微摩尔范围内。这种动态共价文库和筛选方法可用于鉴定可逆地组装在其他核酸靶标上的化合物。
• Design, synthesis and evaluation of progesterone–adenine hybrids as bivalent inhibitors of P-glycoprotein-mediated multidrug efflux
  作者：Waël Zeinyeh、Ghina Alameh、Sylvie Radix、Catherine Grenot、Charles Dumontet、Nadia Walchshofer

  DOI：10.1016/j.bmcl.2010.03.085

  日期：2010.5

  Steroidal bivalent ligands were designed on the basis of the described closer proximity of the ATP-site and the putative steroid-binding site of P-glycoprotein (ABCB1). The syntheses of seven progesterone-adenine hybrids were described. Their abilities to inhibit P-glycoprotein-mediated daunorubicin efflux in K562/R7 human leukemic cells overexpressing P-glycoprotein were evaluated versus progesterone. (C) 2010 Elsevier Ltd. All rights reserved.
• Progesterone–adenine hybrids as bivalent inhibitors of P-glycoprotein-mediated multidrug efflux: Design, synthesis, characterization and biological evaluation
  作者：Waël Zeinyeh、Zahia Mahiout、Sylvie Radix、Thierry Lomberget、Axel Dumoulin、Roland Barret、Catherine Grenot、Luc Rocheblave、Eva-Laure Matera、Charles Dumontet、Nadia Walchshofer

  DOI：10.1016/j.steroids.2012.07.010

  日期：2012.10

  Bivalent ligands were designed on the basis of the described close proximity of the ATP-site and the putative steroid-binding site of P-glycoprotein (ABCB1). The syntheses of 19 progesterone-adenine hybrids are described. Their abilities to inhibit P-glycoprotein-mediated daunorubicin efflux in K562/R7 human leukemic cells overexpressing P-glycoprotein were evaluated versus progesterone. The hybrid with a hexamethylene linker chain showed the best inhibitory potency. The efficiency of these progesterone-adenine hybrids depends on two main factors: (i) the nature of the linker and (ii) its attachment point on the steroid skeleton. (C) 2012 Elsevier Inc. All rights reserved.