(E)-1-(4-methoxyphenyl)-3-(quinolin-6-yl)prop-2-en-1-one | 130520-46-6

• 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: (E)-1-(4-methoxyphenyl)-3-(quinolin-6-yl)prop-2-en-1-one
• 英文别名: (2E)-1-(4-methoxyphenyl)-3-(6-quinolinyl)-2-propen-1-one；(E)-1-(4-methoxyphenyl)-3-quinolin-6-ylprop-2-en-1-one
• CAS: 130520-46-6
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: JRUSCYIWTRRNBN-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-methoxyphenyl)-3-(quinolin-6-yl)prop-2-en-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到(2E)-1-(4-methoxyphenyl)-3-(1-oxo-6-quinolinyl)-2-propen-1-one
  参考文献：
  名称：

  Quinolinyl and quinolinyl N-oxide chalcones: Synthesis, antifungal and cytotoxic activities

  摘要：

  A series of new 6-quinolinyl and quinolinyl N-oxide chalcones were efficiently prepared. All chalcones were tested by minimal inhibitory concentration (MIC) against three species of Candida, Cryptococcus gattii and Paracoccidioides brasiliensis. The effect of these compounds was also tested on the survival and growth of the human cancer cell lines UACC-62 (melanoma), MCF-7 (breast), TK-10 (renal) and leukemic cells, Jurkat and HL60. The compounds tested presented strong activity against P. brasiliensis, most importantly compound 4e. C gattii also presented interesting susceptibility for compounds 5b and 5f. The cytotoxic activity showed that compounds 3c and 4e, presented the best activity against MCF-7 and TK-10. For leukemic cells the compounds 4f, 3g, 4g and 5g have shown the best activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.019
• 作为产物：
  描述：

  6-甲基喹啉 在 selenium(IV) oxide 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 (E)-1-(4-methoxyphenyl)-3-(quinolin-6-yl)prop-2-en-1-one
  参考文献：
  名称：

  Quinolinyl and quinolinyl N-oxide chalcones: Synthesis, antifungal and cytotoxic activities

  摘要：

  A series of new 6-quinolinyl and quinolinyl N-oxide chalcones were efficiently prepared. All chalcones were tested by minimal inhibitory concentration (MIC) against three species of Candida, Cryptococcus gattii and Paracoccidioides brasiliensis. The effect of these compounds was also tested on the survival and growth of the human cancer cell lines UACC-62 (melanoma), MCF-7 (breast), TK-10 (renal) and leukemic cells, Jurkat and HL60. The compounds tested presented strong activity against P. brasiliensis, most importantly compound 4e. C gattii also presented interesting susceptibility for compounds 5b and 5f. The cytotoxic activity showed that compounds 3c and 4e, presented the best activity against MCF-7 and TK-10. For leukemic cells the compounds 4f, 3g, 4g and 5g have shown the best activity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.019

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