3-(hexyloxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(hexyloxy)-1-phenyl-1H-pyrazole-4-carbaldehyde
• 英文别名: 3-Hexoxy-1-phenylpyrazole-4-carbaldehyde；3-hexoxy-1-phenylpyrazole-4-carbaldehyde
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: BTYOLDCHYHHZBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(hexyloxy)-1-phenyl-1H-pyrazole-4-carbaldehyde 在 caesium carbonate 、 二甲基亚砜 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 4-ethynyl-3-(hexyloxy)-1-phenyl-1H-pyrazole
  参考文献：
  名称：

  [EN] PYRAZOLE-INDOLE CONJUGATES FOR PHOTODYNAMIC TREATMENT OF CANCER AND BACTERIAL INFECTIONS
  [FR] CONJUGUÉS PYRAZOLE-INDOLE POUR LE TRAITEMENT PHOTODYNAMIQUE DU CANCER ET D'INFECTIONS BACTÉRIENNES

  摘要：

  本发明涉及通过乙烯、丁烯-1,3或乙炔连接剂结合的新吡唑-吲哚衍生物，其中在通式I的R1、R2和R3位置含有取代基，可用于癌症或细菌感染的光动力疗法。该发明还包括含有结合的吡唑-吲哚衍生物的药物组合物。(I)

  公开号：

  WO2021164795A1

文献信息

• Synthesis and photodynamic properties of pyrazole-indole hybrids in the human skin melanoma cell line G361
  作者：Gabrielė Varvuolytė、Lukáš Malina、Aurimas Bieliauskas、Barbora Hošíková、Helena Simerská、Hana Kolářová、Neringa Kleizienė、Vladimír Kryštof、Algirdas Šačkus、Asta Žukauskaitė

  DOI：10.1016/j.dyepig.2020.108666

  日期：2020.12

  Three conjugated pyrazole-indole hybrids, 5, 7 and 10, were synthesized from easily accessible 3-(hexyloxy)-1-phenyl-1H-pyrazole-4-carbaldehyde 1 and 5-iodo-3,3-dimethyl-2-phenyl-3H-indole 4 employing olefination reactions (Wittig, Ramirez), Vilsmeier-Haack formylation and palladium-catalysed cross coupling reactions (ligand-free Heck, Sonogashira). The compounds displayed no cytotoxicity in the melanoma cell line G361 unless irradiated with visible blue light (414 nm), and the potency of the compounds increased with light intensity. Lead compound 7 displayed EC50 values of 3.08, 0.26 and 0.05 mu M in cells irradiated with 1, 10 and 50 J/cm(2), respectively. The following experiments revealed increased levels of reactive oxygen species in treated cells and a decrease in JC-1 polymer aggregation within the mitochondria, suggesting mitochondrial membrane depolarization. In addition, extensive DNA fragmentation was detected using the comet assay and by detection of phosphorylated histone H2A.X, the level of which increased with both increased compound concentration and irradiation energy. In control experiments, cells kept either in the dark or without compound 7 did not show any DNA damage. Overall, the results demonstrated that fluorescent pyrazole-indole hybrids may serve as an interesting source of photosensitizing compounds with anticancer activity.