| 1242983-32-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• CAS: 1242983-32-9
• 化学式: C₂₅H₂₉NO₇
• 分子量: 455.508
• InChiKey: DXAFPTLFKMMAQR-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.5h， 以59%的产率得到2-[5-(2,4-dimethoxy-phenyl)-1H-pyrazol-3-yl]-6-(2-hydroxymethyl-1-methyl-pyrrolidin-3-yl)-3,5-dimethoxy-phenol
  参考文献：
  名称：

  Synthesis of novel 3,5-diaryl pyrazole derivatives using combinatorial chemistry as inhibitors of tyrosinase as well as potent anticancer, anti-inflammatory agents

  摘要：

  In the present article, we have synthesized a combinatorial library of 3,5-diaryl pyrazole derivatives using 8-(2-(hydroxymethyl)-1-methylpyrrolidin-3-yl)-5,7-dimethoxy-2-phenyl-4H-chromen-4-one (1) and hydrazine hydrate in absolute ethyl alcohol under the refluxed conditions. The structures of the compounds were established by IR, (1)H NMR and mass spectral analysis. All the synthesized compounds were evaluated for their anticancer activity against five cell lines (breast cancer cell line, prostate cancer cell line, promyelocytic leukemia cell line, lung cancer cell line, colon cancer cell line) and anti-inflammatory activity against TNF-alpha and IL-6. Out of 15 compounds screened, 2a and 2d exhibited promising anticancer activity (61-73% at 10 mu M concentration) against all selected cell lines and IL-6 inhibition (47% and 42% at 10 mu M concentration) as in comparison to standard flavopiridol (72-87% inhibition at 0.5 mu M) and dexamethasone (85% inhibition at 1 mu M concentration), respectively. Cytotoxicity of the compounds checked using CCK-8 cell lines and found to be nontoxic to slightly toxic. Out of 15, four 3,5-diaryl pyrazole derivatives exhibiting potent inhibitory activities against both the monophenolase and diphenolase actions of tyrosinase. The IC(50) values of compounds (2a, 2d, 2h and 21) for monophenolase inhibition were determined to range between 1.5 and 30 mu M. Compounds 2a, 2d, 2h and 21 also inhibited diphenolase significantly with IC(50) values of 29.4, 21.5, 2.84 and 19.6 mu M, respectively. All four 3,5-diaryl pyrazole derivatives were active as tyrosinase inhibitors (2a, 2d, 2h and 21), and belonging to competitive inhibitors. Interestingly, they all manifested simple reversible slow-binding inhibition against diphenolase. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.06.046