5-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1,3,4-oxadiazole-2-thiol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-[1-(3-fluoro-4-phenylphenyl)ethyl]-3H-1,3,4-oxadiazole-2-thione
• 化学式: C₁₆H₁₃FN₂OS
• 分子量: 300.356
• InChiKey: IGZRWTZGYRSNNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-3-羟基乙酰苯 、 5-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1,3,4-oxadiazole-2-thiol 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以60%的产率得到2-((5-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1,3,4-oxadiazol-2-yl)thio)-1-(3-hydroxyphenyl)ethan-1-one
  参考文献：
  名称：

  Flurbiprofen derivatives as novel α-amylase inhibitors: Biology-oriented drug synthesis (BIODS), in vitro, and in silico evaluation

  摘要：

  Novel derivatives of flurbiprofen 1-18 including flurbiprofen hydrazide 1, substituted aroyl hydrazides 2-9, 2-mercapto oxadiazole derivative 10, phenacyl substituted 2-mercapto oxadiazole derivatives 11-15, and benzyl substituted 2-mercapto oxadiazole derivatives 16-18 were synthesized and characterized by EI-MS, H-1 and C-13 NMR spectroscopic techniques. All derivatives 1-18 were screened for alpha-amylase inhibitory activity and demonstrated a varying degree of potential ranging from IC50 = 1.04 +/- 0.3 to 2.41 +/- 0.09 mu M as compared to the standard acarbose (IC50 = 0.9 +/- 0.04 mu M). Out of eighteen compounds, derivatives 2 (IC50 = 1.69 +/- 0.1 mu M), 3 (IC50 = 1.04 +/- 0.3 mu M), 9 (IC50 = 1.25 +/- 1.05 mu M), and 13 (IC50 = 1.6 +/- 0.18 mu M) found to be excellent inhibitors while rest of the compounds demonstrated comparable inhibition potential. A limited structure-activity relationship (SAR) was established by looking at the varying structural features of the library. In addition to that, in silico study was conducted to understand the binding interactions of the compounds (ligands) with the active she of alpha-amylase enzyme.

  DOI：

  10.1016/j.bioorg.2018.07.038
• 作为产物：
  描述：

  氟比洛芬 在 二硫化碳 、 hydrazine hydrate 、 硫酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 22.0h， 生成 5-(1-(2-fluoro-[1,1′-biphenyl]-4-yl)ethyl)-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  2,5-二取代-1,3,4-恶二唑衍生物的合成、计算研究、抗氧化和抗炎生物评价

  摘要：

  通过掺入氟比洛芬部分合成了 1,3,4-恶二唑衍生物 Ox-6a-f，旨在探索目标分子减少氧化应激的潜力。通过简单的反应制备了标题化合物Ox-6a-f，其中氟比洛芬-COOH基团在酸催化介质中用甲醇酯化，然后与肼反应得到相应的酰肼。然后通过在 KOH 存在下与 CS2 反应，将酰肼环化为 1,3,4-恶二唑-2-硫醇。标题化合物Ox-6a-f是通过-SH基团与各种烷基/芳基氯的反应合成的，其中涉及S-烷基化反应。通过光谱数据确定了合成的 Ox-6a-f 衍生物的结构。针对靶蛋白环加氧酶 2 COX-2 (PDBID 5KIR) 和环加氧酶 1 COX-1 (PDBID 6Y3C) 进行计算机分子对接，以确定合成化合物与这些结构的结合亲和力。据推测，与6Y3C相比，大多数合成的化合物与5KIR的活性结合位点结合良好，特别是化合物Ox-6f在所有合成的化合物Ox-6a-f中显示出优异的结合亲和力（7

  DOI：

  10.3390/ph16071045

文献信息

• Flurbiprofen derivatives as novel α-amylase inhibitors: Biology-oriented drug synthesis (BIODS), in vitro, and in silico evaluation
  作者：Momin Khan、Aftab Alam、Khalid Mohammed Khan、Uzma Salar、Sridevi Chigurupati、Abdul Wadood、Farman Ali、Jahidul Islam Mohammad、Muhammad Riaz、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.07.038

  日期：2018.12

  Novel derivatives of flurbiprofen 1-18 including flurbiprofen hydrazide 1, substituted aroyl hydrazides 2-9, 2-mercapto oxadiazole derivative 10, phenacyl substituted 2-mercapto oxadiazole derivatives 11-15, and benzyl substituted 2-mercapto oxadiazole derivatives 16-18 were synthesized and characterized by EI-MS, H-1 and C-13 NMR spectroscopic techniques. All derivatives 1-18 were screened for alpha-amylase inhibitory activity and demonstrated a varying degree of potential ranging from IC50 = 1.04 +/- 0.3 to 2.41 +/- 0.09 mu M as compared to the standard acarbose (IC50 = 0.9 +/- 0.04 mu M). Out of eighteen compounds, derivatives 2 (IC50 = 1.69 +/- 0.1 mu M), 3 (IC50 = 1.04 +/- 0.3 mu M), 9 (IC50 = 1.25 +/- 1.05 mu M), and 13 (IC50 = 1.6 +/- 0.18 mu M) found to be excellent inhibitors while rest of the compounds demonstrated comparable inhibition potential. A limited structure-activity relationship (SAR) was established by looking at the varying structural features of the library. In addition to that, in silico study was conducted to understand the binding interactions of the compounds (ligands) with the active she of alpha-amylase enzyme.
• Amir, Mohammad; Kumar, Pharmazie, 2005, vol. 60, # 3, p. 175 - 180
  作者：Amir, Mohammad、Kumar

  DOI：——

  日期：——
• Synthesis, Computational Studies, Antioxidant and Anti-Inflammatory Bio-Evaluation of 2,5-Disubstituted-1,3,4-Oxadiazole Derivatives
  作者：Sibghat Mansoor Rana、Muhammad Islam、Hamid Saeed、Hummera Rafique、Muhammad Majid、Muhammad Tahir Aqeel、Fariha Imtiaz、Zaman Ashraf

  DOI：10.3390/ph16071045

  日期：——

  fluctuation was observed in case of Ox-6f, which forms the most stable complex with COX-2. The comprehensive antioxidant potential of the synthesized compounds has been evaluated by determining their free radical scavenging activity, including DPPH, OH, nitric oxide (NO), and iron chelation assay. The derivative Ox-6f showed promising results with 80.23% radical scavenging potential at a dose of 100 µg/mL while

  通过掺入氟比洛芬部分合成了 1,3,4-恶二唑衍生物 Ox-6a-f，旨在探索目标分子减少氧化应激的潜力。通过简单的反应制备了标题化合物Ox-6a-f，其中氟比洛芬-COOH基团在酸催化介质中用甲醇酯化，然后与肼反应得到相应的酰肼。然后通过在 KOH 存在下与 CS2 反应，将酰肼环化为 1,3,4-恶二唑-2-硫醇。标题化合物Ox-6a-f是通过-SH基团与各种烷基/芳基氯的反应合成的，其中涉及S-烷基化反应。通过光谱数据确定了合成的 Ox-6a-f 衍生物的结构。针对靶蛋白环加氧酶 2 COX-2 (PDBID 5KIR) 和环加氧酶 1 COX-1 (PDBID 6Y3C) 进行计算机分子对接，以确定合成化合物与这些结构的结合亲和力。据推测，与6Y3C相比，大多数合成的化合物与5KIR的活性结合位点结合良好，特别是化合物Ox-6f在所有合成的化合物Ox-6a-f中显示出优异的结合亲和力（7
• Flurbiprofen Derivatives as Potential DPPH and ABTS Radical Scavengers
  作者：M. Khan、A. Alam、U. Salar、S. Chigurupati、F. Saleem、S. Hameed、M. Taha、Kh. M. Khan

  DOI：10.1134/s1070428023090154

  日期：2023.9