3-[3-[2-(trifluoromethyl)phenyl]prop-2-enoyl]chromen-2-one | 1575622-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-[3-[2-(trifluoromethyl)phenyl]prop-2-enoyl]chromen-2-one
• CAS: 1575622-48-8
• 化学式: C₁₉H₁₁F₃O₃
• 分子量: 344.29
• InChiKey: AQKAQCIQIVGXSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[3-[2-(trifluoromethyl)phenyl]prop-2-enoyl]chromen-2-one 在 potassium hydrogencarbonate 、 一水合肼 、 potassium iodide 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 3-(1-(2-(4-nitrophenylthio)acetyl)-5-(2-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Novel coumarin-dihydropyrazole thio-ethanone derivatives: Design, synthesis and anticancer activity

  摘要：

  A series novel 1-(3-substituted-5-pheny1-4,5-dihydropyrazol-1-y1)-2-thio-ethanone derivatives as potential telomerase inhibitors were designed and synthesized. The bioassays demonstrated that compounds 4a, 4f, 4j and 7b, 7d occupied high antiproliferative activity against SGC-7901, MGC-803, Bcap-37 and HEPG-2 cell lines. By a modified TRAP assay, some title compounds were tested against telomerase, and compound 4f showed the most potent inhibitory activity with IC50 value at 0.92 +/- 0.09 mu M. The mechanism of antitumor action indicated that title compounds 4f and 7b could suppress cell proliferation through inducing cell cycle arrest in G0/G1 phase. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.014
• 作为产物：
  描述：

  水杨醛 在 哌啶 、 哌嗪 作用下， 以 正丁醇 为溶剂， 反应 14.33h， 生成 3-[3-[2-(trifluoromethyl)phenyl]prop-2-enoyl]chromen-2-one
  参考文献：
  名称：

  Novel 2H-chromen derivatives: design, synthesis and anticancer activity

  摘要：

  我们设计并合成了一系列与 2H-chromen 连接的新型二氢吡唑衍生物。所有化合物都对 MGC-803、Bcap-37、SGC-7901 和 HepG2 细胞系进行了体外抗增殖活性筛选。结果表明，化合物 4a 和 10a 对 HepG2 细胞具有很强的抑制活性，对 GES-1 和 L-02 细胞株无明显毒性。对一些标题化合物进行了端粒酶测试，结果表明化合物 10a 的抑制活性最强，IC50 值为 0.98 ± 0.11 μM，能很好地与 TERT 的活性位点相匹配。研究还进一步探讨了其抗细胞增殖的分子机制，结果表明化合物 10a 可抑制 hTERT 的表达和 Wnt/β-catenin 信号转导。

  DOI：

  10.1039/c3ra47252c

文献信息

• New arylpyrazoline-coumarins: Synthesis and anti-inflammatory activity
  作者：Liu Zeng Chen、Wei Wei Sun、Li Bo、Jie Quan Wang、Cheng Xiu、Wen Jian Tang、Jing Bo Shi、Hai Pin Zhou、Xin Hua Liu

  DOI：10.1016/j.ejmech.2017.06.044

  日期：2017.9

  the highest anti-inflammatory activity with inhibiting IL-6, TNF-α and nitric oxide (NO) production lipopolysaccharide (LPS)-stimulated. The further study showed that title compound 4m could significantly suppress expressions of nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) and the productions of IL-6, TNF-α, NO through NF-κB/MAPK signaling pathway. The anti-inflammatory activity of compound

  开发具有改善的药物型材新抗炎剂，一系列新的苯基吡唑啉香豆素衍生物的（图4a〜4米）设计并合成。通过X射线晶体学测定化合物4a和4b。已经通过评估其对LPS诱导的IL-6释放的抑制作用来筛选所有化合物的抗炎活性。其中，化合物4m表现出最高的抗炎活性，具有抑制IL-6，TNF-α和一氧化氮（NO）产生的脂多糖（LPS）刺激的作用。进一步的研究表明标题化合物4m通过NF-κB/ MAPK信号通路可以显着抑制一氧化氮合酶（iNOS），环氧合酶-2（COX-2）的表达以及IL-6，TNF-α，NO的产生。化合物4m的抗炎活性由角叉菜胶诱导的爪水肿确定。此外，体内评估结果表明，化合物4m可以抑制AA诱导的大鼠踝关节。
• Dihydropyrazole derivatives as telomerase inhibitors: Structure-based design, synthesis, SAR and anticancer evaluation in vitro and in vivo
  作者：Yang Wang、Fei Xiong Cheng、Xiao Long Yuan、Wen Jian Tang、Jing Bo Shi、Chen Zhong Liao、Xin Hua Liu

  DOI：10.1016/j.ejmech.2016.02.009

  日期：2016.4

  It is of our interest to generate and identify novel compounds with regulation telomerase for cancer therapy. In order to carry out more rational design, based on structure-based drug design, several series of N-substituted-dihydropyrazole derivatives, totally 78 compounds as potential human telomerase inhibitors were designed and synthesized. The results demonstrated that some compounds had potent anticancer activity against four tumor cell lines, and showed good selectivity on tumor cells over somatic cells. By the modified TRAP assay, compound 13i exhibited the most potent inhibitory activity against telomerase with an IC50 value of 0.98 mu M. In vivo evaluation results indicated that compound 13i could inhibit growth of S180 and HepG2 tumor-bearing mice, and it also significantly enhanced the survival rate of EAC tumor-bearing mice. The further results in vivo confirmed that it could significantly improve pathological changes of N,N-diethylnitrosamine (DEN)-induced rat hepatic tumor. These data support further studies to assess rational design of more efficient telomerase inhibitors in the future. (C) 2016 Elsevier Masson SAS. All rights reserved.