2-bromo-1-(3-nitro-4-fluorophenyl)ethan-1-one | 153398-67-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-1-(3-nitro-4-fluorophenyl)ethan-1-one
• 英文别名: 2-bromo-1-(4-fluoro-3-nitrophenyl)ethan-1-one；2-Bromo-1-(4-fluoro-3-nitrophenyl)ethanone
• CAS: 153398-67-5
• 化学式: C₈H₅BrFNO₃
• 分子量: 262.035
• InChiKey: MLXCTIXPBRLFAI-UHFFFAOYSA-N

物化性质

• 沸点：
  311.4±27.0 °C(Predicted)
• 密度：
  1.744±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo-1-(3-nitro-4-fluorophenyl)ethan-1-one 在 三氯氧磷 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 2-Chloro-6-(4-fluoro-3-nitrophenyl)imidazo[2,1-b][1,3]thiazole-5-carbaldehyde
  参考文献：
  名称：

  Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors

  摘要：

  The activity of a series of imidazo[2,1-b]thiazole guanylhydrazones as inhibitors of p90 ribosomal S6 kinase 2 (RSK2) is described. It was found that a small subset of compounds show both potent inhibition of RSK2 kinase activity and tumor cell growth in vitro. Detailed study of one of the most active compounds indicates a high degree of selectivity for inhibition of RSK2 compared to a spectrum of other related kinases. Selective inhibition of the MCF-7 breast tumor cell line compared to MCF-10A non-transformed cells, as well as selective inhibition of the biomarker GSK3 provides evidence that the compounds can affect the RSK2 target in cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.001
• 作为产物：
  描述：

  2-溴-4'-氟苯乙酮 在 硝酸 作用下， 反应 1.0h， 生成 2-bromo-1-(3-nitro-4-fluorophenyl)ethan-1-one
  参考文献：
  名称：

  Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors

  摘要：

  The activity of a series of imidazo[2,1-b]thiazole guanylhydrazones as inhibitors of p90 ribosomal S6 kinase 2 (RSK2) is described. It was found that a small subset of compounds show both potent inhibition of RSK2 kinase activity and tumor cell growth in vitro. Detailed study of one of the most active compounds indicates a high degree of selectivity for inhibition of RSK2 compared to a spectrum of other related kinases. Selective inhibition of the MCF-7 breast tumor cell line compared to MCF-10A non-transformed cells, as well as selective inhibition of the biomarker GSK3 provides evidence that the compounds can affect the RSK2 target in cells. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.001

文献信息

• [EN] 2-AMINOIMIDAZOLE-PHENYL DERIVATIVES USEFUL FOR CONTROLLING MICROBIAL GROWTH<br/>[FR] DÉRIVÉS DE 2-AMINOIMIDAZOLE-PHÉNYLE UTILES POUR LUTTER CONTRE LA CROISSANCE MICROBIENNE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2018169752A1

  公开（公告）日：2018-09-20

  Provided are 2-aminoimidazole-phenyl derivative compounds of Formula (I): which compounds are useful in methods of controlling microbial growth, such as by enhancing the effects of an antibiotic administered in combination with the compound. Compositions including these compounds, devices including these compounds, and methods of using the same are also provided.

  提供了公式（I）的2-氨基咪唑-苯衍生物化合物，这些化合物在控制微生物生长的方法中很有用，例如通过增强与该化合物联合给药的抗生素的效果。还提供了包括这些化合物的组合物、包括这些化合物的设备以及使用它们的方法。
• Scaffold-Hopping Strategy on a Series of Proteasome Inhibitors Led to a Preclinical Candidate for the Treatment of Visceral Leishmaniasis
  作者：Michael Thomas、Stephen Brand、Manu De Rycker、Fabio Zuccotto、Iva Lukac、Peter G. Dodd、Eun-Jung Ko、Sujatha Manthri、Kate McGonagle、Maria Osuna-Cabello、Jennifer Riley、Caterina Pont、Frederick Simeons、Laste Stojanovski、John Thomas、Stephen Thompson、Elisabet Viayna、Jose M. Fiandor、Julio Martin、Paul G. Wyatt、Timothy J. Miles、Kevin D. Read、Maria Marco、Ian H. Gilbert

  DOI：10.1021/acs.jmedchem.1c00047

  日期：2021.5.13

  a compound with in vivo efficacy, which was hampered by poor solubility and genotoxicity. The work on the original scaffold failed to lead to developable compounds, so an extensive scaffold-hopping exercise involving medicinal chemistry design, in silico profiling, and subsequent synthesis was utilized, leading to the preclinical candidate. The compound was shown to act via proteasome inhibition, and

  内脏利什曼病 (VL) 是一种严重影响东非、亚洲和南美洲大片地区的寄生虫感染，迫切需要新的治疗方法。我们之前报道了 GSK3494245/DDD01305143 ( 1 ) 作为 VL 的临床前候选者的发现，并且在本文中，我们报告了导致其鉴定的药物化学程序。对表型筛选的命中进行了优化，以提供具有体内功效的化合物，但由于溶解度差和遗传毒性而受到阻碍。原始支架上的工作未能产生可开发的化合物，因此在计算机上进行了涉及药物化学设计的广泛支架跳跃练习分析和随后的合成被利用，导致临床前候选人。该化合物被证明通过蛋白酶体抑制起作用，我们报告了将不同支架建模成冷冻电镜结构以及这对我们理解该系列的结构-活性关系的影响。
• COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF PARASITIC DISEASES
  申请人：VIDAL Agnes

  公开号：US20160045505A1

  公开（公告）日：2016-02-18

  The present invention provides compounds of formula (I): (Formula (I)) or a pharmaceutically acceptable salt, tautomer, or stereoisomer, thereof, wherein the variables are as defined herein. The present invention further provides pharmaceutical compositions comprising such compounds and methods of using such compounds for treating, preventing, inhibiting, ameliorating, or eradicating the pathology and/or symptomology of a disease caused by a parasite, such as Leishmaniasis, Human African Trypanosomiasis and Chagas disease.

  本发明提供了公式（I）的化合物：（公式（I）），或其药学上可接受的盐，互变异构体或立体异构体，其中变量如定义所述。本发明还提供了包括这种化合物的制药组合物和使用这种化合物治疗、预防、抑制、改善或根除由寄生虫引起的疾病的方法，例如利什曼病、非洲人类锥虫病和恰加斯病。
• Dimeric 2-aminoimidazoles are highly active adjuvants for gram-positive selective antibiotics against Acinetobacter baumannii
  作者：Santiana A. Marrujo、Veronica B. Hubble、Jingdong Yang、Man Wang、Ansley M. Nemeth、Samantha L. Barlock、Dane Juarez、Richard D. Smith、Roberta J. Melander、Robert K. Ernst、Mayland Chang、Christian Melander

  DOI：10.1016/j.ejmech.2023.115329

  日期：2023.3

  Previously, we reported aryl 2-aminoimidazole (2-AI) adjuvants that potentiate macrolide antibiotics against A. baumannii. Macrolide antibiotics are typically used to treat infections caused by gram-positive bacteria, but are ineffective against most gram-negative bacteria. We describe a new class of dimeric 2-AIs that are highly active macrolide adjuvants, with lead compounds lowering minimum inhibitory

  美国疾病控制与预防中心 (CDC) 报告称，自 2019 年以来，医院获得性感染增加了 65%。主要致病菌之一是革兰氏阴性菌鲍曼不动杆菌。此前，我们报道了芳基 2-氨基咪唑 (2-AI) 佐剂可增强大环内酯类抗生素对抗鲍曼不动杆菌的作用。大环内酯类抗生素通常用于治疗革兰氏阳性菌引起的感染，但对大多数革兰氏阴性菌无效。我们描述了一类新型二聚体 2-AI，它们是高活性大环内酯佐剂，其先导化合物可将针对鲍曼不动杆菌的最低抑制浓度 (MIC) 降低至或低于革兰氏阳性断点水平。母体二聚体将克拉霉素 (CLR) 对鲍曼不动杆菌5075 的 MIC 从 32 μg/mL 降低至 7.5 μM (3.4 μg/mL) 的 1 μg/mL，随后的结构活性关系 (SAR) 研究发现了几种化合物活动。该先导化合物在 1.5 μM (0.72 μg/mL) 时将 CLR MIC 降低至 2 μg/mL，远远超过母体二聚体和之前的先导芳基
• 2-AMINOIMIDAZOLE-PHENYL DERIVATIVES USEFUL FOR CONTROLLING MICROBIAL GROWTH
  申请人：NORTH CAROLINA STATE UNIVERSITY

  公开号：US20220000118A1

  公开（公告）日：2022-01-06

  Provided are 2-aminoimidazole-phenyl derivative compounds of Formula (I): which compounds are useful in methods of controlling microbial growth, such as by enhancing the effects of an antibiotic administered in combination with the compound. Compositions including these compounds, devices including these compounds, and methods of using the same are also provided.