| 1044499-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• CAS: 1044499-45-7
• 化学式: C₁₄H₁₁N₃O₃
• 分子量: 269.26
• InChiKey: SDSIKDONWSBZOF-CYBMUJFWSA-N

反应信息

• 作为产物：
  描述：

  在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 甲酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以78%的产率得到
  参考文献：
  名称：

  Asymmetric Synthesis of 2,3-Dihydro-2-arylquinazolin-4-ones: Methodology and Application to a Potent Fluorescent Tubulin Inhibitor with Anticancer Activity

  摘要：

  For several decades the 2,3-dihydroquinazolinone (DHQZ) heterocycle has been known to possess a variety of important biological and medicinal properties. Despite the many interesting facets of these molecules, synthetic access to nonracemic DHQZ analogues has remained elusive. Herein, we disclose a synthetic route that allows access to either enantiomer of a variety of DHQZ derivatives. We illustrate the utility of this chemistry with the asymmetric preparation and biological evaluation of a new chiral fluorescent tubulin binding agent with extremely potent antiproliferative properties against human cancer cells. A computational rationale for the increased potency of the (S)-enantiomer over the (R)-enantiomer is given, based on the crystal structure of alpha,beta-tubulin complexed with colchicine. Taking advantage of the inherent fluorescence of these molecules, confocal images of GMC-5-193 (compound 7) in the cytoplasm of human melanoma cells (MDA-MB-435) cells are presented.

  DOI：

  10.1021/jm800271c