3,4-difluoro-N-(2-hydroxyethoxy)-benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4-difluoro-N-(2-hydroxyethoxy)-benzene
• 英文别名: (S)-(3,4-difluorophenyl)ethylene glycol；(3,4-difluorophenyl)ethylene glycol；2-(3,4-difluorophenoxy)ethanol
• 化学式: C₈H₈F₂O₂
• 分子量: 174.147
• InChiKey: AEFHUHARYNZQOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-difluoro-N-(2-hydroxyethoxy)-benzene 在 sodium hydride 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 22.5h， 生成 4-[(3S)-1-[2-(3,4-difluorophenoxy)ethyl]-5-oxopyrrolidin-3-yl]-4-methyl-1λ⁶-thiane-1,1-dione
  参考文献：
  名称：

  Fragment-Based Approach to the Development of an Orally Bioavailable Lactam Inhibitor of Lipoprotein-Associated Phospholipase A2 (Lp-PLA₂)

  摘要：

  Lp-PLA(2) has been explored as a target for a number of inflammation associated diseases, including cardiovascular disease and dementia. This article describes the discovery of a new fragment derived chemotype that interacts with the active site of Lp-PLA(2). The starting fragment hit was discovered through an X-ray fragment screen and showed no activity in the bioassay (IC50 > 1 mM). The fragment hit was optimized using a variety of structure-based drug design techniques, including virtual screening, fragment merging, and improvement of shape complementarity. A novel series of Lp-PLA(2) inhibitors was generated with low lipophilicity and a promising pharmacokinetic profile.

  DOI：

  10.1021/acs.jmedchem.6b01427
• 作为产物：
  描述：

  碳酸乙烯酯 、 3,4-二氟苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3,4-difluoro-N-(2-hydroxyethoxy)-benzene
  参考文献：
  名称：

  Fragment-Based Approach to the Development of an Orally Bioavailable Lactam Inhibitor of Lipoprotein-Associated Phospholipase A2 (Lp-PLA₂)

  摘要：

  Lp-PLA(2) has been explored as a target for a number of inflammation associated diseases, including cardiovascular disease and dementia. This article describes the discovery of a new fragment derived chemotype that interacts with the active site of Lp-PLA(2). The starting fragment hit was discovered through an X-ray fragment screen and showed no activity in the bioassay (IC50 > 1 mM). The fragment hit was optimized using a variety of structure-based drug design techniques, including virtual screening, fragment merging, and improvement of shape complementarity. A novel series of Lp-PLA(2) inhibitors was generated with low lipophilicity and a promising pharmacokinetic profile.

  DOI：

  10.1021/acs.jmedchem.6b01427

文献信息

• Discovery of New Anti-MRSA Agents Based on Phenoxyethanol and Its Mechanism
  作者：Jinxin Xie、Lijuan Wang、Xiaoyong Zhang、Yiyang Li、Xin Liao、Caixin Yang、Ri-Yuan Tang

  DOI：10.1021/acsinfecdis.2c00365

  日期：2022.11.11

  Methicillin-resistant Staphylococcus aureus (MRSA) poses a severe threat to public health and safety. The discovery and development of novel anti-MRSA drugs with a new mode of action are a challenge. In this study, a class of novel aryloxyethyl propiolates and their homologues as anti-MRSA agents have been designed and synthesized based on phenoxyethanol, of which compound II-39 showed high inhibitory

  耐甲氧西林金黄色葡萄球菌(MRSA) 对公众健康和安全构成严重威胁。发现和开发具有新作用模式的新型抗 MRSA 药物是一项挑战。本研究基于苯氧乙醇设计合成了一类新型芳氧乙基丙炔酸酯及其同系物作为抗 MRSA 药物，其中化合物II-39对 MRSA 具有较高的抑制活性，MIC 为 0.78 μg/mL，MBC 3.13 μg/mL，优于万古霉素。化合物II-39可以破坏细胞壁和细胞膜，抑制生物膜的形成，通过静电和沟槽相互作用与MRSA的DNA结合。蛋白质组学和代谢组学研究表明，化合物II-39影响 MRSA 的多种细胞内代谢途径。值得注意的是，化合物II-39可有效抑制 CrtPQMN 蛋白的表达并阻断毒力因子（葡萄黄素）的生物合成。因此，芳氧乙基丙炔酸酯及其同系物是有前途的多靶点抗 MRSA 药物。
• (Meth)acrylate compound, additive for optical resin, optical element, and optical device
  申请人：NIKON CORPORATION

  公开号：US11142636B2

  公开（公告）日：2021-10-12

  Provided is an additive for an optical resin including a (meth)acrylate compound represented by general formula (1) below: [in general formula (1), each X independently represents a fluorine atom or a methyl group in which at least one hydrogen atom is substituted with a fluorine atom; m represents an integer of 0 to 5; R1 represents an alkylene group or an oxyalkylene group having a carbon number of 1 to 8; and R2 represents a hydrogen atom or a methyl group].

  本发明提供了一种光学树脂添加剂，其中包括如下通式 (1) 所代表的（甲基）丙烯酸酯化合物： [在通式（1）中，每个 X 独立地代表氟原子或甲基，其中至少有一个氢原子被氟原子取代；m 代表 0 至 5 的整数；R1 代表碳原子数为 1 至 8 的亚烷基或氧亚烷基；R2 代表氢原子或甲基]。
• (METH)ACRYLATE COMPOUND, ADDITIVE FOR OPTICAL RESIN, OPTICAL ELEMENT, AND OPTICAL DEVICE
  申请人：NIKON CORPORATION

  公开号：US20190322857A1

  公开（公告）日：2019-10-24

  Provided is an additive for an optical resin including a (meth)acrylate compound represented by general formula (1) below: [in general formula (1), each X independently represents a fluorine atom or a methyl group in which at least one hydrogen atom is substituted with a fluorine atom; m represents an integer of 0 to 5; R 1 represents an alkylene group or an oxyalkylene group having a carbon number of 1 to 8; and R 2 represents a hydrogen atom or a methyl group].