3-(5-mercapto-1,3,4-oxadiazol-2-yl)naphthalen-2-ol | 332377-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(5-mercapto-1,3,4-oxadiazol-2-yl)naphthalen-2-ol
• 英文别名: 5-(3-Hydroxy-naphthalen-2-yl)-3H-[1,3,4]oxadiazole-2-thione；5-(3-hydroxynaphthalen-2-yl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 332377-26-1
• 化学式: C₁₂H₈N₂O₂S
• 分子量: 244.274
• InChiKey: NSJJMAAZIZVAPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 3-(5-mercapto-1,3,4-oxadiazol-2-yl)naphthalen-2-ol 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 生成 4-(5-(3-hydroxynaphthalen-2-yl)-1,3,4-oxadiazol-2-ylthio)-but-2-ynyl 4-fluorobenzoate
  参考文献：
  名称：

  Discovery of Potent and Selective Inhibitors of Human Reticulocyte 15-Lipoxygenase-1

  摘要：

  There are a variety of lipoxygenases in the human body (hLO), each having a distinct role in cellular biology. Human reticulocyte 15-lipoxygenase-1 (15-hLO-1), which catalyzes the dioxygenation of 1,4-cis,cis-pentadiene-containing polyunsaturated fatty acids, is implicated in a number of diseases including cancer, atherosclerosis, and neurodegenerative conditions. Despite the potential therapeutic relevance of this target, few inhibitors have been reported that are both potent and selective. To this end, we have employed a quantitative high-throughput (qHTS) screen against similar to 74000 small molecules in search of reticulocyte 15-hLO-1 selective inhibitors. This screen led to the discovery of a novel chemotype for 15-hLO-1 inhibition, which displays nM potency and is > 7500-fold selective against the related isozymes, 5-hLO, platelet 12-hLO, epithelial 15-hLO-2, ovine cyclooxygenase-1, and human cyclooxygenase-2. In addition, kinetic experiments were performed which indicate that this class of inhibitor is tight binding, reversible, and appears not to reduce the active-site ferric ion.

  DOI：

  10.1021/jm1008852
• 作为产物：
  描述：

  二硫化碳 、 3-羟基-2-萘酸肼 在 N,N-二甲基甲酰胺 作用下， 反应 25.0h， 以85%的产率得到3-(5-mercapto-1,3,4-oxadiazol-2-yl)naphthalen-2-ol
  参考文献：
  名称：

  超声辅助、低溶剂和无酸/碱合成 5-取代的 1,3,4-oxadiazole-2-硫醇作为有效的抗菌剂和抗氧化剂。

  摘要：

  摘要 绿色化学的目标之一是使用环保溶剂或去除和减少有害废溶剂的体积。在这项研究中，提出了一种通过芳基酰肼与 CS 2的超声辅助反应合成 5-取代的 1,3,4-恶二唑-2-硫醇衍生物的新工艺。（1:1 摩尔比）在没有碱性或酸性催化剂的情况下加入几滴 DMF。它们在易于处理和纯化的条件下以良好至极好的产率生产。为了证明所制备化合物的有效性，通过DPPH自由基清除、连续双重微量稀释和划线板法筛选了它们的抗氧化、抗菌和抗真菌潜力。用合成的杂环观察到可接受的显着抑制活性。结果表明，5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol ( 3c ) 是一种广谱抗菌剂。其中许多显示出与标准对照（抗坏血酸和α-生育酚）。合成的 1,3,4-恶二唑也是治疗癌症、帕金森、炎症​​和糖尿病疾病的有效候选药物。 图形摘要 通过一种新的、高效的绿色工艺制备了 18 种 5-取代的

  DOI：

  10.1007/s11030-020-10125-y

文献信息

• Discovery of Potent and Selective Inhibitors of Human Reticulocyte 15-Lipoxygenase-1
  作者：Ganesha Rai、Victor Kenyon、Ajit Jadhav、Lena Schultz、Michelle Armstrong、J. Brian Jameson、Eric Hoobler、William Leister、Anton Simeonov、Theodore R. Holman、David J. Maloney

  DOI：10.1021/jm1008852

  日期：2010.10.28

  There are a variety of lipoxygenases in the human body (hLO), each having a distinct role in cellular biology. Human reticulocyte 15-lipoxygenase-1 (15-hLO-1), which catalyzes the dioxygenation of 1,4-cis,cis-pentadiene-containing polyunsaturated fatty acids, is implicated in a number of diseases including cancer, atherosclerosis, and neurodegenerative conditions. Despite the potential therapeutic relevance of this target, few inhibitors have been reported that are both potent and selective. To this end, we have employed a quantitative high-throughput (qHTS) screen against similar to 74000 small molecules in search of reticulocyte 15-hLO-1 selective inhibitors. This screen led to the discovery of a novel chemotype for 15-hLO-1 inhibition, which displays nM potency and is > 7500-fold selective against the related isozymes, 5-hLO, platelet 12-hLO, epithelial 15-hLO-2, ovine cyclooxygenase-1, and human cyclooxygenase-2. In addition, kinetic experiments were performed which indicate that this class of inhibitor is tight binding, reversible, and appears not to reduce the active-site ferric ion.
• Ultrasound-assisted, low-solvent and acid/base-free synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols as potent antimicrobial and antioxidant agents
  作者：Elahe Yarmohammadi、Hamid Beyzaei、Reza Aryan、Ashraf Moradi

  DOI：10.1007/s11030-020-10125-y

  日期：2021.11

  broad-spectrum antimicrobial agent. Many of them displayed remarkable antioxidant properties comparable to standard controls (ascorbic acid and α-tocopherol). Synthesized 1,3,4-oxadiazoles are also potent candidates to treat cancer, Parkinson, inflammatory, and diabetes diseases. Graphic Abstract Eighteen 5-substituted 1,3,4-oxadiazole-2-thiol derivatives as potent antimicrobial and antioxidant agents were prepared

  摘要 绿色化学的目标之一是使用环保溶剂或去除和减少有害废溶剂的体积。在这项研究中，提出了一种通过芳基酰肼与 CS 2的超声辅助反应合成 5-取代的 1,3,4-恶二唑-2-硫醇衍生物的新工艺。（1:1 摩尔比）在没有碱性或酸性催化剂的情况下加入几滴 DMF。它们在易于处理和纯化的条件下以良好至极好的产率生产。为了证明所制备化合物的有效性，通过DPPH自由基清除、连续双重微量稀释和划线板法筛选了它们的抗氧化、抗菌和抗真菌潜力。用合成的杂环观察到可接受的显着抑制活性。结果表明，5-(4-fluorophenyl)-1,3,4-oxadiazole-2-thiol ( 3c ) 是一种广谱抗菌剂。其中许多显示出与标准对照（抗坏血酸和α-生育酚）。合成的 1,3,4-恶二唑也是治疗癌症、帕金森、炎症​​和糖尿病疾病的有效候选药物。 图形摘要 通过一种新的、高效的绿色工艺制备了 18 种 5-取代的