5-[4-(4-Methoxyphenyl)triazol-1-yl]quinolin-8-ol | 1209000-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-[4-(4-Methoxyphenyl)triazol-1-yl]quinolin-8-ol
• CAS: 1209000-32-7
• 化学式: C₁₈H₁₄N₄O₂
• 分子量: 318.335
• InChiKey: HDPDKFZXOPMMMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  73.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[4-(4-Methoxyphenyl)triazol-1-yl]quinolin-8-ol 在 sodium chloride 、 sodium hydroxide 、 magnesium chloride 、 4-羟乙基哌嗪乙磺酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensors

  摘要：

  Protein phosphorylation is a ubiquitous post-translational modification, and protein kinases, the enzymes that catalyze the phosphoryl transfer, are involved in nearly every aspect of normal, as well as aberrant, cell function. Here we describe the synthesis of novel. red-shifted 8-hydroxyquinoline-based fluorophores and their incorporation into peptidyl kinase activity reporters. Replacement of the sulfonamide group of the sulfonamido-oxine (1, Sox) chromophore, which has been previously used In kinase sensing, by a 1,4-substituted triazole moiety prepared via click chemistry resulted in a significant bathochromic shift in the fluorescence excitation (15 nm) and emission (40 rim) maxima for the Mg2+ chelate. Furthermore, when a click derivative was incorporated into a chemosensor for MK2, the kinase accepted the new substrate as efficiently as the previously reported Sox-based sensor. Taken together, these results extend the utility range of kinase sensors that are based on chelation-enhanced fluorescence (CHEF).

  DOI：

  10.1021/jo901369k
• 作为产物：
  描述：

  8-羟基喹啉 在 吡啶 、 盐酸 、 copper(ll) sulfate pentahydrate 、 palladium on activated charcoal 、 硝酸 、 碳酸氢钠 、 potassium hydroxide 、 维生素 C 、 肼 、 sodium nitrite 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 32.75h， 生成 5-[4-(4-Methoxyphenyl)triazol-1-yl]quinolin-8-ol
  参考文献：
  名称：

  抗分枝杆菌 8-羟基喹啉衍生物作为结核分枝杆菌烯酰基载体蛋白还原酶体外酶抑制剂的鉴定

  摘要：

  耐药菌株的日益流行刺激了新候选药物的发现。其中包括具有抗菌特性的8-羟基喹啉（8HQ）衍生物。不幸的是，缺乏评估此类主要针对烯酰酰基载体蛋白还原酶（InhA）的可能靶标的数据，而InhA是该领域经过验证的靶标。因此，本研究的主要目的是鉴定对 InhA 有活性的 8HQ 衍生物。最初，针对微生物的小型抗菌文库及其与 InhA 抑制剂具有一定结构相似性的新衍生物的筛选确定了四种 7-取代-8HQ（系列 、 和 ）和四种 5-取代-8HQ 活性衍生物（系列 、 、和 ）。一般来说，7-取代的 8-HQ 更有效，并且在酶测定中能够在低微摩尔范围内抑制 InhA。然而，具有抗分枝杆菌活性的 5-取代-8-HQ 不能抑制 InhA。这些发现表明 8-HQ 衍生物的非混杂性质，并强调选择适当取代基以实现酶抑制的重要性。最后，7-取代-8HQ 系列是基于结构的药物设计和进一步开发的有前途的新衍生物。

  DOI：

  10.1016/j.bioorg.2024.107705

文献信息

• Synthesis of Red-Shifted 8-Hydroxyquinoline Derivatives Using Click Chemistry and Their Incorporation into Phosphorylation Chemosensors
  作者：Juan A. González-Vera、Elvedin Luković、Barbara Imperiali

  DOI：10.1021/jo901369k

  日期：2009.10.2

  Protein phosphorylation is a ubiquitous post-translational modification, and protein kinases, the enzymes that catalyze the phosphoryl transfer, are involved in nearly every aspect of normal, as well as aberrant, cell function. Here we describe the synthesis of novel. red-shifted 8-hydroxyquinoline-based fluorophores and their incorporation into peptidyl kinase activity reporters. Replacement of the sulfonamide group of the sulfonamido-oxine (1, Sox) chromophore, which has been previously used In kinase sensing, by a 1,4-substituted triazole moiety prepared via click chemistry resulted in a significant bathochromic shift in the fluorescence excitation (15 nm) and emission (40 rim) maxima for the Mg2+ chelate. Furthermore, when a click derivative was incorporated into a chemosensor for MK2, the kinase accepted the new substrate as efficiently as the previously reported Sox-based sensor. Taken together, these results extend the utility range of kinase sensors that are based on chelation-enhanced fluorescence (CHEF).
• 10.1016/j.bioorg.2024.107705
  作者：Joaquim, Angélica Rocha、Lopes, Marcela Silva、Fortes, Isadora Serraglio、de Bem Gentz, Caroline、de Matos Czeczot, Alexia、Perelló, Marcia Alberton、Roth, Candida Deves、Vainstein, Marilene Henning、Basso, Luiz Augusto、Bizarro, Cristiano Valim、Machado, Pablo、de Andrade, Saulo Fernandes

  DOI：10.1016/j.bioorg.2024.107705

  日期：——

  screening against the microorganism of a small antimicrobial library and its new derivatives that possess some structural similarity with InhA inhibitors identified four 7-substituted-8HQ (series , , and ) and four 5-substituted-8HQ active derivatives (series , , and ). In general, the 7-substituted 8-HQs were more potent and, in the enzymatic assay, were able to inhibit InhA at low micromolar range

  耐药菌株的日益流行刺激了新候选药物的发现。其中包括具有抗菌特性的8-羟基喹啉（8HQ）衍生物。不幸的是，缺乏评估此类主要针对烯酰酰基载体蛋白还原酶（InhA）的可能靶标的数据，而InhA是该领域经过验证的靶标。因此，本研究的主要目的是鉴定对 InhA 有活性的 8HQ 衍生物。最初，针对微生物的小型抗菌文库及其与 InhA 抑制剂具有一定结构相似性的新衍生物的筛选确定了四种 7-取代-8HQ（系列 、 和 ）和四种 5-取代-8HQ 活性衍生物（系列 、 、和 ）。一般来说，7-取代的 8-HQ 更有效，并且在酶测定中能够在低微摩尔范围内抑制 InhA。然而，具有抗分枝杆菌活性的 5-取代-8-HQ 不能抑制 InhA。这些发现表明 8-HQ 衍生物的非混杂性质，并强调选择适当取代基以实现酶抑制的重要性。最后，7-取代-8HQ 系列是基于结构的药物设计和进一步开发的有前途的新衍生物。