4-(2-bromoethyl)-1H-imidazole hydrochloride | 791634-10-1

• 英文名称: 4-(2-bromoethyl)-1H-imidazole hydrochloride
• 英文别名: 4(5)-(2-bromoethyl)imidazole hydrochloride；4-(2-bromoethyl)imidazole hydrochloride
• CAS: 791634-10-1
• 化学式: C₅H₇BrN₂*ClH
• 分子量: 211.489
• InChiKey: BNMWPFVTDXQWEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  28.68
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(苄氧基)氨基甲酸叔丁酯 、 4-(2-bromoethyl)-1H-imidazole hydrochloride 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.0h， 以47%的产率得到tert-butyl (2-(1H-imidazol-4-yl)ethyl)(benzyloxy)carbamate
  参考文献：
  名称：

  A Latent Oxazoline Electrophile for N−O−C Bond Formation in Pseudomonine Biosynthesis

  摘要：

  Nitrogen-heteroatom bonds figure prominently in the structural, chemical, and functional diversity of natural products. In the case of Pseudomonas siderophore pseudomonine, an N-O hydroxamate linkage is found uncommonly configured in an isoxazolidinone ring. In an effort to understand the biogenesis of this heterocycle, we have characterized the pseudomonine synthetase in vitro and reconstituted the complete biosynthetic pathway. Our results indicate that the isoxazolidinone of pseudomonine arises from spontaneous rearrangement of an oxazoline precursor. To the best of our knowledge, this is a previously uncharacterized mode of post-assembly line heterocyclization. Our results establish the oxygen of the ubiquitous siderophore hydroxamate functionality as a nucleophile and may be indicative of general strategy for N-O-C bond formation in nature.

  DOI：

  10.1021/ja804499r
• 作为产物：
  描述：

  histamine dichloride 在 硫酸 、 potassium bromide 、 sodium nitrite 作用下， 以90%的产率得到4-(2-bromoethyl)-1H-imidazole hydrochloride
  参考文献：
  名称：

  鲑鱼气单胞菌亚种中铁-不动杆菌素外膜受体的鉴定 沙门氏菌与合成不动杆菌类似物的构效关系

  摘要：

  鲑气单胞菌亚种。沙门氏菌是几种鱼类中糠un菌病的病原体，会产生不动杆菌素和阿莫那丁作为铁载体。在先前的研究中，我们对这些铁载体进行了化学表征，并提出了基于遗传分析的生物合成途径。但是，铁-乙酰细菌素和铁-氨苄菌素的内在化机制仍然是未知的。在本研究中，我们证明外膜蛋白FSTB是三价铁acinetobactin受体A.鲑因为一个FSTB有缺陷的突变体不能在铁限制下生长，并且不使用不动杆菌素作为铁源。为了研究不动杆菌素的结构变化对其铁载体活性的影响，合成了一系列不动杆菌素基类似物，包括其对映异构体和四个脱甲基衍生物。与fstB（-）菌株相比，这些类似物对fstB（+）菌株的生物活性可阐明结构-活性关系。我们发现缺乏对映体偏好的不动杆菌素对沙门氏菌的铁载体活性或对FstB蛋白受体的分子识别。另外，观察到鲑鱼曲霉当结构中不存在咪唑或类似的杂环时，不能使用不动杆菌素类似物。出人意料的是，除去异恶唑烷酮

  DOI：

  10.1021/acschembio.6b00805

文献信息

• Rigid Oxazole Acinetobactin Analog Blocks Siderophore Cycling in <i>Acinetobacter baumannii</i>
  作者：Tabbetha J. Bohac、Justin A. Shapiro、Timothy A. Wencewicz

  DOI：10.1021/acsinfecdis.7b00146

  日期：2017.11.10

  The emergence of multidrug resistant (MDR) Gram-negative bacterial pathogens has raised global concern. Nontraditional therapeutic strategies, including antivirulence approaches, are gaining traction as a means of applying less selective pressure for resistance in vivo. Here, we show that rigidifying the structure of the siderophore preacinetobactin from MDR Acinetobacter baumannii via oxidation of

  多药耐药（MDR）革兰氏阴性细菌病原体的出现引起了全球关注。非传统的治疗策略，包括抗病毒方法，正逐渐受到人们的关注，这是一种为体内抗药性施加较小选择性压力的方法。在这里，我们表明，通过将酚盐-恶唑啉部分氧化为酚盐-恶唑，使耐多药鲍曼不动杆菌中的铁载体前葡萄球菌素的结构刚性化，将产生有效的铁载体抑制剂，并在类似感染的低微摩尔浓度下产生抑菌作用。条件。
• Triggering DNAzymes with Light:  A Photoactive C8 Thioether-Linked Adenosine
  作者：Richard Ting、Leonard Lermer、David M. Perrin

  DOI：10.1021/ja046964y

  日期：2004.10.1

  Herein we report evidence for a light-inducible DNAzyme. In so doing, we also disclose the synthesis and photochemical properties of a novel nucleoside: 8-(2-(4-imidazolyl)ethyl-1-thio)-2'-deoxyriboadenosine (d1). The light sensitivity of (d1) was evaluated via an examination of the photoinduced reactivation of DNAzyme 8-17E from an inactive form that contained a single nucleotide (d1) modification. Restoration of DNAzyme activity results from a photoinduced reversion of (d1) to unmodified deoxyadenosine. Deuterium studies indicate that water is the source of hydrogen in the C8-H product and not the alkylthio group, suggesting that reversion of (1) to adenosine is not a consequence of simple homolysis of the C8-S bond but of an unprecedented photochemical conversion. This adenosine, which affords significant control of catalytic reactivation of a DNAzyme, may find general use in photodecaging other biological systems.
• Design and synthesis of 3-isoxazolidone derivatives as new Chlamydia trachomatis inhibitors
  作者：S. Abdelsayed、N.T. Ha Duong、J. Hai、M. Hémadi、J.M. El Hage Chahine、P. Verbeke、N. Serradji

  DOI：10.1016/j.bmcl.2014.06.056

  日期：2014.8

  Chlamydia trachomatis (Ct) is a bacterial human pathogen responsible for the development of trachoma, the worldwide infection leading to blindness, and is also a major cause of sexually transmitted diseases. As iron is an essential metabolite for this bacterium, iron depletion presents a promising strategy to limit Ct proliferation. The aim of this study is to synthesize 3-isoxazolidone derivatives bearing known chelating moieties in an attempt to develop new bactericidal anti-Chlamydiaceae molecules. We have investigated the paths by which these new compounds affect Ct serovar L2 development in HeLa cells, in the presence or absence of exogenously added iron. The iron-chelating properties of these molecules were also determined. Our data reveal important bactericidal effects which are distinguishable from those due to iron chelation.
• [EN] SMALL-MOLECULE AGENTS WITH ANTIVIRAL ACTIVITY AGAINST RNA VIRUSES<br/>[FR] AGENTS À PETITES MOLÉCULES AYANT UNE ACTIVITÉ ANTIVIRALE CONTRE DES VIRUS À ARN
  申请人：[en]FUNDACIÓN UNIVERSIDAD CATÓLICA DE VALENCIA SAN VICENTE MÁRTIR

  公开号：WO2022175384A1

  公开（公告）日：2022-08-25

  The present invention relates to the use of small organic compounds, or a salt or solvate thereof, for the treatment and/or prevention of viral infections by RNA-viruses, preferably from the familyCoronaviridae, Orthomyxoviridae, Filoviridae, Flaviviridae, Retroviridae and Togaviridae, such as SARS-CoV-2.