3,3'-[（3,4,5-三氟苯基）亚甲基]双[4-羟基-2H-1-苯并吡喃-2-酮]“，'分子量'：'466.37 | 1210283-33-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3,3'-[（3,4,5-三氟苯基）亚甲基]双[4-羟基-2H-1-苯并吡喃-2-酮]“，'分子量'：'466.37
• 英文名称: 3,3'-(3,4,5-trifluorobenzylidene)-bis-(4-hydroxycoumarin)
• 英文别名: 3,3'-((3,4,5-trifluorophenyl)methylene)bis(4-hydroxy-2H-chromen-2-one)；3,3'-(3,4,5-Trifluorobenzylidene)bis(4-hydroxy-2H-1-benzopyran-2-one)；4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)-(3,4,5-trifluorophenyl)methyl]chromen-2-one
• CAS: 1210283-33-2
• 化学式: C₂₅H₁₃F₃O₆
• 分子量: 466.37
• InChiKey: XNLZNNUNTQKWPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 3,4,5-三氟苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以57%的产率得到3,3'-[（3,4,5-三氟苯基）亚甲基]双[4-羟基-2H-1-苯并吡喃-2-酮]“，'分子量'：'466.37
  参考文献：
  名称：

  Antibacterial and Antitumor Activities of Biscoumarin and Dihydropyran Derivatives

  摘要：

  通过一锅多组分缩合反应合成了一系列新型双香豆素（1-4）和二氢吡喃（5-13）衍生物，并对其抗菌和抗肿瘤活性进行了体外评估。四个代表性化合物 3、7、9 和 11 的 X 射线晶体结构分析证实了这些化合物的结构。在总共 13 种衍生物中，化合物 1-4 的抗肿瘤活性最强；尤其是化合物 1 和 2，它们也是具有较好抗菌活性的抗菌成员。此外，密度泛函理论（DFT）结果表明，与化合物 3 和 4 相比，双香豆素 1 和 2 的分子内氢键（HB）能量较低。

  DOI：

  10.3390/molecules200917614

文献信息

• COUMARIN-BASED COMPOUNDS FOR THE TREATMENT OF ALZHEIMER'S DISEASE AND CANCER
  申请人：Zhu Lei

  公开号：US20110306605A1

  公开（公告）日：2011-12-15

  Compounds including those of the Formula I where X, R 1 , R 2 and subscript t are as defined herein, useful as γ-secretase inhibitors, are provided, as are compositions comprising the compounds, as well as methods for use of the compounds for treating or preventing neurodegenerative diseases, such as, for instance, Alzheimer's disease.

  提供包括公式I中的化合物，其中X，R1，R2和下标t的定义如本文所述，这些化合物作为γ-分泌酶抑制剂有用，提供了包括这些化合物的组合物，以及使用这些化合物治疗或预防神经退行性疾病的方法，例如阿尔茨海默病。
• [EN] COUMARIN-BASED COMPOUNDS FOR THE TREATMENT OF ALZHEIMER'S DISEASE AND CANCER<br/>[FR] COMPOSÉS À BASE DE COUMARINE
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2010075280A3

  公开（公告）日：2010-08-19
• [EN] COUMARIN-BASED COMPOUNDS<br/>[FR] COMPOSÉS À BASE DE COUMARINE
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2010075280A2

  公开（公告）日：2010-07-01

  Compounds including those of the Formula I where X, R1, R2 and subscript t are as defined herein, useful as γ-secretase inhibitors, are provided, as are compositions comprising the compounds, as well as methods for use of the compounds for treating or preventing neurodegenerative diseases, such as, for instance, Alzheimer's disease.
• 3,3’-((3,4,5-trifluoropHenyl)methylene)bis(4-hydroxy-2H-chromen-2-one) inhibit lung cancer cell proliferation and migration
  作者：Wenhui Luo、Guoxin Chang、Dingmei Lin、Hongyi Xie、Huilong Sun、Zhibin Li、Shirong Mo、Ruixue Wang、Yan Wang、Zhaoguang Zheng

  DOI：10.1371/journal.pone.0303186

  日期：——

  Lung cancer is a major public health challenge and, despite therapeutic improvements, is the first leading cause of cancer worldwide. The current cure rate from advanced cancer treatment is excessively low. Therefore, it is of great importance to identify novel, potent and less toxic anticancer agents for the treatment of lung cancer. The aim of our research is to synthesize a new biscoumarin 3,3’-((3,4,5-trifluorop -phenyl)methylene)bis(4-hydroxy-2H-chromen-2-one) (C35) as an anticancer agent. C35 was simply prepared by 4-hydroxycoumarin and 3,4,5-trifluorobenzaldehyde under ethanol and its structure was analyzed by spectroscopic analyses. The anti-proliferation effect of C35 was detected using CCK-8 assay. Migration abilities were measured by Transwell assay. The expression of correlated proteins was determined by Western blot. The results showed that C35 displayed strong cytostatic effects on lung cancer cell proliferation. In addition, C35 possessed a significant inhibition of migration by reducing the expression of matrix metalloproteinases-2 (MMP-2) and MMP-9 in lung cancer cells. Furthermore, C35 treatment suppressed the phosphorylation of p38 in lung cancer cells. Moreover, in vivo experiments were carried out, in which we treated Lewis tumor-bearing C57 mice via intraperitoneal injection of C35. Results showed that C35 inhibited tumor growth in vivo. In conclusion, our study demonstrated the anticancer activity of C35 via suppression of lung cancer cell proliferation and migration, which is possibly involved with the inhibition of the p38 pathway.