(2E)-1-phenyl-3-(quinoxalin-6-yl)-2-propen-1-one | 1357063-34-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-phenyl-3-(quinoxalin-6-yl)-2-propen-1-one
• 英文别名: Phenyl-3-(quinoxalin-6-yl)prop-2-en-1-one；(E)-1-phenyl-3-quinoxalin-6-ylprop-2-en-1-one
• CAS: 1357063-34-3
• 化学式: C₁₇H₁₂N₂O
• 分子量: 260.295
• InChiKey: MLZGULNJUUZRRX-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-1-phenyl-3-(quinoxalin-6-yl)-2-propen-1-one 在 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 36.0h， 生成 4-Oxo-4-(3-phenyl-5-quinoxalin-6-yl-4,5-dihydro-pyrazol-1-yl)-butyric acid
  参考文献：
  名称：

  METHANOGEN INHIBITORS

  摘要：

  The present invention relates to a new class of methanogen inhibitors for ruminants. The invention also extends to the use of such compounds in ruminants to reduce methane production in the rumen and/or to enhance productivity in the ruminant.

  公开号：

  WO2024039250A1
• 作为产物：
  描述：

  (喹噁啉-6-基)甲醇 在 pyridinium chlorochromate 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2E)-1-phenyl-3-(quinoxalin-6-yl)-2-propen-1-one
  参考文献：
  名称：

  Activity of novel quinoxaline-derived chalcones on in vitro glioma cell proliferation

  摘要：

  Gliomas are the most common and devastating tumors of the central nervous system (CNS). Many pieces of evidence point out the relevance of natural compounds for cancer therapy and prevention, including chalcones. In the present study, eight synthetic quinoxaline-derived chalcones, structurally based on the selective PI3K gamma inhibitor AS605240, were evaluated for anti-proliferative activity and viability inhibition using glioma cell lines from human and rat origin (U-138 MG and C6, respectively), at different time-periods of incubation and concentrations. The results revealed that four chalcones (compounds 1, 6, 7 and 8), which present methoxy groups at A-ring, displayed higher efficacies and potencies, being able to inhibit either cell proliferation or viability, in a time- and concentration-dependent manner, with an efficacy that was greater than that seen for the positive control compound AS605240. Flow cytometry analysis demonstrated that incubation of C6 cells with compound 6 led to Cl phase arrest, likely indicating an interference with apoptosis. Furthermore, compound 6 was able to visibly inhibit ART activation, allied to the stimulation of ERR MAP-kinase. The chalcones tested herein, especially those displaying a methoxy substituent, might well represent promising molecules for the adjuvant treatment of glioma progression. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.023

文献信息

• Design, synthesis and biological evaluation of chalcone derivatives as potent and orally active hCYP3A4 inhibitors
  作者：Shiwei Lu、Feng Zhang、Jiahao Gong、Jian Huang、Guanghao Zhu、Yitian Zhao、Qi Jia、Yiming Li、Bo Li、Kaixian Chen、Weiliang Zhu、Guangbo Ge

  DOI：10.1016/j.bmcl.2023.129435

  日期：2023.10

  metabolic clearance of ∼50% therapeutic drugs. CYP3A4 inhibitors have been used for improving the in vivo efficacy of hCYP3A4-substrate drugs. However, most of existing hCYP3A4 inhibitors may trigger serious adverse effects or undesirable effects on endogenous metabolism. This study aimed to discover potent and orally active hCYP3A4 inhibitors from chalcone derivatives and to test their anti-hCYP3A4

  人细胞色素 P450 3A4 (hCYP3A4) 是最重要的药物代谢酶之一，催化约50% 治疗药物的代谢清除。CYP3A4抑制剂已被用于提高hCYP3A4底物药物的体内功效。然而，大多数现有的hCYP3A4抑制剂可能会引发严重的副作用或对内源代谢产生不良影响。本研究旨在从查耳酮衍生物中发现有效的口服活性 hCYP3A4 抑制剂，并在体外和体内测试其抗 hCYP3A4 作用。经过三轮筛选和结构优化，发现异喹啉查尔酮类化合物具有优异的抗hCYP3A4作用。SAR 研究表明，在 A 环上引入异喹啉环可显着增强抗 CYP3A4 作用，产生A10 (IC 50  = 102.10 nM) 作为一种有前途的先导化合物。第二轮SAR研究表明，在B环羰基对位引入取代基可显着提高抗CYP3A4效果。结果，C6被确定为人肝微粒体 (HLM) 中最有效的 hCYP3A4 抑制剂 (IC 50  = 43.93