(E)-1-(4'-fluoro[1,1'-biphenyl]-2-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one

• 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'-fluoro[1,1'-biphenyl]-2-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-5-(3-(4'-fluoro[1,1'-biphenyl]-2-yl)-3-oxoprop-1-en-1-yl)-2-methoxyphenol；(E)-1-[2-(4-fluorophenyl)phenyl]-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₂₂H₁₇FO₃
• 分子量: 348.374
• InChiKey: AHNXFULTPHTTDJ-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4'-fluoro[1,1'-biphenyl]-2-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one 在 三甲基溴硅烷 、 三乙胺 作用下， 以 甲醇 、 四氯化碳 、 二氯甲烷 、 氯仿 为溶剂， 反应 2.0h， 生成 (E)-(5-(3-(4'-fluoro[1,1'-biphenyl]-2-yl)-3-oxoprop-1-en-1-yl)-2-methoxyphenol)phosphate ester
  参考文献：
  名称：

  O-Phenyl Chalcone Compounds And Preparation Method And Use Thereof

  摘要：

  揭示了一种 o-苯基查尔酮化合物及其制备方法和用途。这些 o-苯基查尔酮化合物能够抑制肿瘤细胞微管的聚集，影响细胞的有丝分裂，并具有较高的抗肿瘤活性。这些化合物还在纳摩尔浓度下对各种肿瘤细胞的增殖具有抑制活性，如人卵巢癌细胞A2780、人结肠癌细胞HCT8、人乳腺癌细胞MCF7、人肺癌细胞A549、人结肠癌细胞SW480、人鼻咽癌细胞CNE2、人肝癌细胞HepG2等。

  公开号：

  US20160333033A1
• 作为产物：
  描述：

  2'-溴苯乙酮 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 0.5h， 生成 (E)-1-(4'-fluoro[1,1'-biphenyl]-2-yl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  O-Phenyl Chalcone Compounds And Preparation Method And Use Thereof

  摘要：

  揭示了一种 o-苯基查尔酮化合物及其制备方法和用途。这些 o-苯基查尔酮化合物能够抑制肿瘤细胞微管的聚集，影响细胞的有丝分裂，并具有较高的抗肿瘤活性。这些化合物还在纳摩尔浓度下对各种肿瘤细胞的增殖具有抑制活性，如人卵巢癌细胞A2780、人结肠癌细胞HCT8、人乳腺癌细胞MCF7、人肺癌细胞A549、人结肠癌细胞SW480、人鼻咽癌细胞CNE2、人肝癌细胞HepG2等。

  公开号：

  US20160333033A1

文献信息

• O-PHENYL CHALCONE COMPOUND AND PREPARATION METHOD AND USE THEREOF
  申请人：Neopanora Bio-Technology (Zhuhai) Ltd.

  公开号：EP3118204B1

  公开（公告）日：2022-04-20
• O-PHENYL CHALCONE COMPOUNDS AND USES THEREOF
  申请人：Sun Yat-Sen University

  公开号：US20170247398A1

  公开（公告）日：2017-08-31

  Disclosed are an o-phenyl chalcone compounds and preparation methods and uses thereof. The o-phenyl chalcone compounds are capable of inhibiting the aggregation of microtubules in tumor cells and influencing the mitosis of the cells, and has a high antitumor activity. The compounds also have inhibitory activity against proliferation on various tumor cells, such as a human ovary cancer cell A2780, a human colon cancer cell HCT8, a human breast cancer cell MCF7, a human lung cancer cell A549, a human colon cancer cell SW480, a human nasopharyngeal carcinoma cell CNE2, a human liver cancer cell HepG2 and the like at nanomole concentrations.
• US9663542B2
  申请人：——

  公开号：US9663542B2

  公开（公告）日：2017-05-30
• US9988405B2
  申请人：——

  公开号：US9988405B2

  公开（公告）日：2018-06-05
• Discovery of Potent Cytotoxic Ortho-Aryl Chalcones as New Scaffold Targeting Tubulin and Mitosis with Affinity-Based Fluorescence
  作者：Cuige Zhu、Yinglin Zuo、Ruimin Wang、Baoxia Liang、Xin Yue、Gesi Wen、Nana Shang、Lei Huang、Yu Chen、Jun Du、Xianzhang Bu

  DOI：10.1021/jm500024v

  日期：2014.8.14

  A series of new ortho-aryl chalcones have been designed and synthesized. Many of these compounds were found to exhibit significant antiproliferation activity toward a panel of cancer cell lines. Selected compounds show potent cytotoxicity against several drug resistant cell lines including paclitaxel (Taxol) resistant human ovarian carcinoma cells, vincristine resistant human ileocecum carcinoma cells, and doxorubicin resistant human breast carcinoma cells. Further investigation revealed that active analogues could inhibit the microtubule polymerization by binding to colchicine site and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. Furthermore, affinity-based fluorescence enhancement was observed during the binding of active compounds with tubulin, which greatly facilitated the determination of tubulin binding site of the compounds. Finally, selected compound 26 was found to exhibit obvious in vivo antitumor activity in A549 tumor xenografts model. Our systematic studies implied a new scaffold targeting tubulin and mitosis for novel antitumor drug discovery.