4-nitroimidazole silver salt | 144330-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-nitroimidazole silver salt
• 英文别名: 4(5)-nitroimidazole silver salt；silver 5-nitro-1H-imidazole；silver;4-nitroimidazol-1-ide
• CAS: 144330-38-1
• 化学式: Ag*C₃H₂N₃O₂
• 分子量: 219.936
• InChiKey: DKGSMKLHPDPFMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-acetyl-β-D-ribofuranosyl bromide 、 4-nitroimidazole silver salt 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 5-Nitro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole
  参考文献：
  名称：

  氨基咪唑核苷酸形成厌氧 5-羟基苯并咪唑：硫胺素和维生素 B12 生物合成的意外交叉点

  摘要：

  细菌硫胺嘧啶合酶 (thiC) 的比较基因组学揭示了 thiC (bzaF) 的旁系同源物与厌氧维生素 B12 生物合成基因聚集在一起。在此，我们证明 BzaF 是一种自由基 S-腺苷甲硫氨酸酶，可催化氨基咪唑核苷酸 (AIR) 显着转化为 5-羟基苯并咪唑 (5-HBI)。我们确定了关键产物原子的起源并提出了反应机制。这些研究代表了解决厌氧维生素 B12 组装中长期存在的问题的第一步，并揭示了硫胺素和维生素 B12 生物合成的意外交叉。

  DOI：

  10.1021/jacs.5b03576
• 作为产物：
  描述：

  水杨酸银 、 4-硝基-3H-咪唑 以 乙醇 为溶剂， 以95%的产率得到4-nitroimidazole silver salt
  参考文献：
  名称：

  ‘Silver bullets’ in antimicrobial chemotherapy: Synthesis, characterisation and biological screening of some new Ag(I)-containing imidazole complexes

  摘要：

  Simple synthetic routes are given to the Ag(I) complexes, [Ag-2(imH)(4)](salH)(2) (imH = imidazole; salH(2) = salicylic acid), (Ag[MeNO(2)imH)(2)]ClO4 center dot nH(2)O (MeNO(2)imH = 2-methyl-5-nitroimidazole; n = 1, 3), [Ag(NO(2)im)] (NO(2)imH = 5-nitroimidazole) and [Ag-(apim)]ClO4 (apim =1-(3-aminopropyl)imidazole). X-ray crystal structures of [Ag-2(imH)(4)](salH)(2), [Ag(MeNO(2)imH)(2)]ClO4 center dot H2O and [Ag(apim)]ClO4 were obtained. The new Ag(I) complexes and related known Ag(I) imidazolates were screened for their growth inhibitory effects (in vitro) against the pathogenic bacteria methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli and also the fungal pathogen Candida albicans. [Ag-2(imH)(4)](salH)(2), in comparison to the prescription drug silver sulfadiazine, had significantly better anti-bacterial qualities, whilst against the fungus C albicans it was 47 times more potent than the marketed drug ketoconazole. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2005.11.021

文献信息

• Biosynthesis of the thiamin pyrimidine: the reconstitution of a remarkable rearrangement reaction
  作者：Brian G. Lawhorn、Ryan A. Mehl、Tadhg P. Begley

  DOI：10.1039/b405429f

  日期：——

  The conversion of 5-aminoimidazole ribonucleotide (AIR) into 4-amino-2-methyl-5-hydroxymethylpyrimidine (HMP) is a fascinating reaction on the thiamin biosynthetic pathway in bacteria and is probably the most complex unresolved rearrangement in primary metabolism. We have successfully reconstituted this reaction in a cell-free system. The E. coli thiC gene product and an additional unidentified E. coli protein are required for the reaction. In addition, SAM and nicotinamide cofactors are required for full activity. Labeling studies to determine the origin of most of the atoms in the pyrimidine are described. Based on these studies, a new mechanism for HMP formation is proposed.

  5-氨基咪唑核苷酸（AIR）转化为4-氨基-2-甲基-5-羟甲基嘧啶（HMP）的反应是细菌硫胺素生物合成途径中的一个迷人反应，可能是初级代谢中最复杂的未解决重排反应。我们已经成功地在无细胞系统中重构了这个反应。E. coli 的 thiC 基因产物以及一个额外的未鉴定的 E. coli 蛋白质是反应所必需的。此外，SAM 和烟酰胺辅因子也是完全活性所需的。我们描述了标记研究，以确定嘧啶中大多数原子的来源。基于这些研究，提出了一种 HMP 形成的新机制。
• A “Radical Dance” in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase
  作者：Abhishek Chatterjee、Amrita B. Hazra、Sameh Abdelwahed、David G. Hilmey、Tadhg P. Begley

  DOI：10.1002/anie.201003419

  日期：2010.11.8

  Tricky things with ThiC: Hydroxymethylpyrimidine phosphate (HMP‐P) synthase (ThiC) catalyzes one of the most complex rearrangement reactions in primary metabolism. Deuteration experiments show that under reducing conditions, in the presence of aminoimidazole ribonucleotide, the 5′‐deoxyadenosyl radical generated at the active site of ThiC reacts directly with the substrate and performs two iterative

  ThiC 的棘手问题：羟甲基嘧啶磷酸 (HMP-P) 合酶 (ThiC) 催化初级代谢中最复杂的重排反应之一。氘化实验表明，在还原条件下，在氨基咪唑核糖核苷酸的存在下，在 ThiC 活性位点产生的 5'-脱氧腺苷自由基直接与底物反应并进行两次迭代氢原子提取事件以催化这种重排（参见方案；SAM = S-腺苷甲硫氨酸）。
• Synthesis of Pyridine-stretched 2′-Deoxynucleosides
  作者：William Fraser、Christopher A. Ramsden、Russell Clayton、Michael L. Davis、Wei Li

  DOI：10.1055/s-2002-33505

  日期：——

  Synthesis of novel pyridine-stretched nucleoside (PSN) analogues of adenine (strA) (1), 2,6-diaminopurine (strD) (15) and hypoxanthine (strH) (17) from 4(5)-nitroimidazole has been achieved. Glycosylation of 4(5)-nitroimidazole was optimized to give consistently good yields (>70%) of the desired analytically pure 5-nitro-1′-β isomer 8 which on hydrogenation, C-addition of ethoxymethylene malononitrile

  已实现从 4(5)-硝基咪唑合成腺嘌呤 (strA) (1)、2,6-二氨基嘌呤 (strD) (15) 和次黄嘌呤 (strH) (17) 的新型吡啶拉伸核苷 (PSN) 类似物。对 4(5)-硝基咪唑的糖基化进行了优化，在氢化、乙氧基亚甲基丙二腈 (EMMN) 的 C-加成和环化过程中，始终获得良好的产率 (>70%) 所需的分析纯 5-硝基-1'-β 异构体 8为PSN合成提供关键中间体14。
• 10.3998/ark.5550190.p010.075
  作者：Clayton, Russell、Davis, Michael L.、Li, Wei、Fraser, William、Ramsden, Christopher A.

  DOI：10.3998/ark.5550190.p010.075

  日期：——
• Segalas, Isabelle; Beauchamp, Andre L., Canadian Journal of Chemistry, 1992, vol. 70, # 3, p. 943 - 951
  作者：Segalas, Isabelle、Beauchamp, Andre L.

  DOI：——

  日期：——