5’-fluoro-2’,2-dihydroxychalcone | 607-84-1

• 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: 5’-fluoro-2’,2-dihydroxychalcone
• 英文别名: 1-(5-Fluor-2-hydroxy-phenyl)-3-(2-hydroxy-phenyl)-prop-2-enon；1-(5-Fluoro-2-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one；1-(5-fluoro-2-hydroxyphenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 607-84-1
• 化学式: C₁₅H₁₁FO₃
• 分子量: 258.249
• InChiKey: BNPQTSKBDWWVKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5’-fluoro-2’,2-dihydroxychalcone 在 双氧水 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 生成 11-fluoro-6H-benzo[7,8][1,4]dioxocino[6,5-b]chromen-9(7H)-one
  参考文献：
  名称：

  包含类黄酮骨架和中型氧杂环的新型四环支架的合成，抗菌活性和分子对接

  摘要：

  描述了一种方便的方法，用于合成新型四环支架，该支架结合了类黄酮骨架和具有中等大小的杂环（八元，九元，十元和十一元环），其中杂环含有来自黄酮醇的烷基，使用不同的二溴代烷烃进行烷基化反应。根据光谱数据和6c的X射线晶体结构建立了合成的化合物。评价合成的化合物的体外抗菌活性。对活性最高的两种化合物6f和6i进行了对接研究。

  DOI：

  10.1016/j.bmcl.2014.12.066
• 作为产物：
  描述：

  5'-fluoro-2'-hydroxy-2-(methoxymethoxy)chalcone 在 硫酸 、 溶剂黄146 作用下， 以66%的产率得到5’-fluoro-2’,2-dihydroxychalcone
  参考文献：
  名称：

  5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer

  摘要：

  Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2'-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum anti-proliferative activity at 5-10 mu M against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.08.069

文献信息

• 一种类黄酮化合物及其制备方法、制剂与应用
  申请人：昆药集团股份有限公司

  公开号：CN107011307B

  公开（公告）日：2019-05-07

  本发明公开了一种类黄酮化合物及其制备方法、制剂与应用。所述的类黄酮化合物的结构如下：其中：X为卤素，R为其他化合物残基。制备方法：所述的类黄酮化合物的合成通式为：所示的查尔酮溶于有机溶剂中，在催化剂作用下，于温度130~140℃下搅拌反应0.3~0.8h，得到目标物类黄酮化合物。制剂为所述的类黄酮化合物中加入药学上可接受的辅料制备。应用为所述的类黄酮化合物在制备抗肿瘤药物中的应用。本发明所述化合物是全新结构的化合物，具有明显的抗肿瘤作用，可用于作为潜在的先导化合物。
• 一种具有抗癌活性的查尔酮化合物及其制备方法、制剂与应用
  申请人：昆药集团股份有限公司

  公开号：CN106831376A

  公开（公告）日：2017-06-13

  本发明公开了一种具有抗癌活性的查尔酮化合物及其制备方法、制剂与应用。所述的具有抗癌活性的查尔酮化合物的结构如下：其中：X为卤素，R为其他化合物残基。制备方法：所述的具有抗癌活性的查尔酮化合物的合成通式为：所示的芳香醛和所示的芳香酮溶于有机溶剂中，在催化剂作用下，回流反应3~8h，反应液用稀盐酸调节pH值至2~6，纯化，干燥得到目标物具有抗癌活性的查尔酮化合物。制剂为所述的具有抗癌活性的查尔酮化合物中加入药学上可接受的辅料制备。应用为所述的具有抗癌活性的查尔酮化合物在制备抗肿瘤药物中的应用。本发明所述化合物是全新结构的化合物，具有明显的抗肿瘤作用，可用于作为潜在的先导化合物。
• 5′-Chloro-2,2′-dihydroxychalcone and related flavanoids as treatments for prostate cancer
  作者：Yohei Saito、Atsushi Mizokami、Hiroyuki Tsurimoto、Kouji Izumi、Masuo Goto、Kyoko Nakagawa-Goto

  DOI：10.1016/j.ejmech.2018.08.069

  日期：2018.9

  Several flavonoids and their biosynthetic precursor chalcones were designed and synthesized to improve the biological effects of the lead compound 2'-hydroxyflavonone against androgen receptor (AR)-dependent transcriptional stimulation. Newly synthesized chalcones 19 and 26 suppressed AR dependent transcription as well as DHT-dependent growth stimulation at a low micromolar level. These compounds were also effective against ligand-independent constitutively active mutant AR derived from castration-resistant PCa (CRPC). Compounds 19 and 26 showed broad spectrum anti-proliferative activity at 5-10 mu M against multiple tumor cell lines including androgen-independent and taxane-resistant prostate cancer as well as a multidrug-resistant subline. Mode of action studies suggested that 19 induced sub-G1 accumulation in PC-3 cells by disrupting the microtubule network without affecting cell cycle progression. Furthermore, the in vivo effectiveness of chalcone 19 was confirmed in a xenograft model antitumor assay. Thus, chalcone 19 has the potential to be a bifunctional lead for treatment of AR-dependent PCa at lower doses as well as AR-independent PCa, including CRPC, at higher doses. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Synthesis, antimicrobial activity and molecular docking of novel tetracyclic scaffolds incorporating a flavonoid framework with medium sized oxygen heterocycles
  作者：Ashok Dongamanti、Vikas Kumar Aamate、Mohan Gandhi Devulapally、Srinivas Gundu、Meena Kumari Kotni、Vijjulatha Manga、Sridhar Balasubramanian、Prasad Ernala

  DOI：10.1016/j.bmcl.2014.12.066

  日期：2015.2

  approach for the synthesis of novel tetracyclic scaffolds incorporating a flavonoid framework with medium sized heterocyclic rings (eight-, nine-, ten- and eleven-membered rings) containing two oxygen atoms from flavonols through alkylation using different dibromoalkanes was described. The synthesized compounds were established based on the spectral data and X-ray crystal structure for 6c. The synthesized

  描述了一种方便的方法，用于合成新型四环支架，该支架结合了类黄酮骨架和具有中等大小的杂环（八元，九元，十元和十一元环），其中杂环含有来自黄酮醇的烷基，使用不同的二溴代烷烃进行烷基化反应。根据光谱数据和6c的X射线晶体结构建立了合成的化合物。评价合成的化合物的体外抗菌活性。对活性最高的两种化合物6f和6i进行了对接研究。