bis(5- f luorobenzo[d]oxazol -2-yl )methane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: bis(5- f luorobenzo[d]oxazol -2-yl )methane
• 英文别名: Bis(5-fluorobenzo[d]oxazol-2-yl)methane；5-fluoro-2-[(5-fluoro-1,3-benzoxazol-2-yl)methyl]-1,3-benzoxazole
• 化学式: C₁₅H₈F₂N₂O₂
• 分子量: 286.238
• InChiKey: ZAVDXPMMEBQAGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙二酸 、 2-氨基-4-氟苯酚 在 polyphosphoric acid 作用下， 以48%的产率得到bis(5- f luorobenzo[d]oxazol -2-yl )methane
  参考文献：
  名称：

  Symmetric bis-benzoxazole-based chemicals exerted anti-inflammatory effect on danger signal LPS-stimulated macrophages

  摘要：

  Inflammatory responses are generated against the danger molecules under normal conditions but excessive or chronic inflammation leads to tissue degeneration and loss of function. To prevent the disease symptoms associated with the inflammatory disorders or the growth of tumor types that require inflammatory environment, generation of immunomodulatory drugs with suppressive functions have great potentials. In this study, we synthesized new generation of anti-proliferative bis-benzoxazole derivatives and tested their anti-inflammatory and anti-cancer potencies. For this purpose, we used a well-characterized mouse macrophage cell line (RAW 264.7). Furthermore, anti-cancer activity of these compounds were tested using MTT assay on prostate (DU145) and breast (MCF7) cancer cells. The screening results revealed that all compounds possessed a high-level anti-inflammatory potential by reducing the expression of inflammatory cytokines in LPS-stimulated macrophages. There were significant and substantial reductions in the secreted TNF alpha, IL6, and IL1 beta levels by chemically treated LPS-induced macrophages compared to non-treated induced ones. Our compounds exerted their anti-inflammatory effect in a dose-dependent manner and they were biologically active even in low nanomolar range concentrations. Bis-benzoxazole derivatives had anti-proliferative effect on MCF-7 and DU-145 cancer cells. Together, our results present a series of new bis-benzoxazole-based compounds with potential therapeutic effects in inflammatory diseases and on tumor cells.

  DOI：

  10.1007/s00706-019-02398-3

文献信息

• Copper‐Catalyzed Oxygenative Skeletal Rearrangement of Tetrahydro‐<i>β</i>‐carbolines Using H₂O and O₂ as Oxygen Sources
  作者：Yu‐Sheng Peng、Wei Wang、Jun Shi、Wei Wu、Jun‐Rong Song、Wei‐Dong Pan、Ge‐Fei Hao、Hai Ren

  DOI：10.1002/anie.202313687

  日期：2023.12.18

  An unprecedented oxygenative skeletal rearrangement reaction of tetrahydro-β-carbolines (THβCs) was developed under mild conditions enabled by copper-catalyzed single-electron transfer oxidation, in which H2O and O2 act as oxygen sources to generate a unique 2-hydroxyl-3-peroxide indoline intermediate. The process involves a multistep sequence to enable the transformation of THβCs to donaxanine-type

  在铜催化单电子转移氧化的温和条件下，开发了前所未有的四氢-β-咔啉（TH β Cs）含氧骨架重排反应，其中H 2 O和O 2作为氧源生成独特的2 -羟基-3-过氧化物二氢吲哚中间体。该过程涉及多步骤序列，以便能够以有效的方式将 TH β Cs 转化为多纳沙宁型杂环。
• US3985763A
  申请人：——

  公开号：US3985763A

  公开（公告）日：1976-10-12
• US4256896A
  申请人：——

  公开号：US4256896A

  公开（公告）日：1981-03-17
• US4260770A
  申请人：——

  公开号：US4260770A

  公开（公告）日：1981-04-07
• Symmetric bis-benzoxazole-based chemicals exerted anti-inflammatory effect on danger signal LPS-stimulated macrophages
  作者：Furkan Ayaz、Ronak Haj Ersan、Oztekin Algul

  DOI：10.1007/s00706-019-02398-3

  日期：2019.6

  Inflammatory responses are generated against the danger molecules under normal conditions but excessive or chronic inflammation leads to tissue degeneration and loss of function. To prevent the disease symptoms associated with the inflammatory disorders or the growth of tumor types that require inflammatory environment, generation of immunomodulatory drugs with suppressive functions have great potentials. In this study, we synthesized new generation of anti-proliferative bis-benzoxazole derivatives and tested their anti-inflammatory and anti-cancer potencies. For this purpose, we used a well-characterized mouse macrophage cell line (RAW 264.7). Furthermore, anti-cancer activity of these compounds were tested using MTT assay on prostate (DU145) and breast (MCF7) cancer cells. The screening results revealed that all compounds possessed a high-level anti-inflammatory potential by reducing the expression of inflammatory cytokines in LPS-stimulated macrophages. There were significant and substantial reductions in the secreted TNF alpha, IL6, and IL1 beta levels by chemically treated LPS-induced macrophages compared to non-treated induced ones. Our compounds exerted their anti-inflammatory effect in a dose-dependent manner and they were biologically active even in low nanomolar range concentrations. Bis-benzoxazole derivatives had anti-proliferative effect on MCF-7 and DU-145 cancer cells. Together, our results present a series of new bis-benzoxazole-based compounds with potential therapeutic effects in inflammatory diseases and on tumor cells.