| 1413919-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• CAS: 1413919-42-2
• 化学式: C₁₆H₁₄ClN₃O₂
• 分子量: 315.759
• InChiKey: YPWODKFTPALPSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  、 在 三乙胺 作用下， 以 乙腈 为溶剂， 以64%的产率得到3-(4-methoxyphenylamino)-2-(5-phenyl-2-(piperazin-1-yl)-thiazol-4-yl)quinazolinone
  参考文献：
  名称：

  Synthesis and screening of 2-(2-(4-substituted piperazine-1-yl)-5-phenylthiazol-4-yl)-3-aryl quinazolinone derivatives as anticancer agents

  摘要：

  Synthesis of novel quinazolinone derivatives was performed from the reaction of N-benzoyl substituted piperazine-1-carbothioamide with 2-chloromethyl quinazolinone derivatives and screened for their in vitro cytotoxic activity by MTT assay. The cell lines used were NCI (human lung cancer cell), MCF 7 (Breast cancer cell), and HEK 293 (Normal epidermal kidney cell). Result of screening on cell line showed moderate to good anticancer activity for all the compounds. Compound 3d (IC50 = 1.1 +/- A 0.03 mu M) was found to be the most active compared to standard methotrexate (IC50 = 2.20 +/- A 0.18 mu M) and 5-florouracil (IC50 = 2.30 +/- A 0.49 mu M). Structure activity relationship of synthesized analogs suggested that the presence of NH linker with aryl moiety at the third position of quinazolinone ring was important for potent anticancer activity. Electron donating group on phenyl ring at the third position of quinazolinone ring gave better anticancer activity then unsubstituted phenyl and electron withdrawing group. Activity by substituted piperazine at 2nd position of thiazole linked with quinazolinone scaffold gave better activity in the order of H > CH3 > CO-C6H5. Our findings may impart new direction to medicinal chemists and biochemists for further investigations of quinazolinone-thiazole containing anticancer agents.

  DOI：

  10.1007/s00044-012-0260-2
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 、 2-chloroacetamidobenzoic acid 在 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and screening of 2-(2-(4-substituted piperazine-1-yl)-5-phenylthiazol-4-yl)-3-aryl quinazolinone derivatives as anticancer agents

  摘要：

  Synthesis of novel quinazolinone derivatives was performed from the reaction of N-benzoyl substituted piperazine-1-carbothioamide with 2-chloromethyl quinazolinone derivatives and screened for their in vitro cytotoxic activity by MTT assay. The cell lines used were NCI (human lung cancer cell), MCF 7 (Breast cancer cell), and HEK 293 (Normal epidermal kidney cell). Result of screening on cell line showed moderate to good anticancer activity for all the compounds. Compound 3d (IC50 = 1.1 +/- A 0.03 mu M) was found to be the most active compared to standard methotrexate (IC50 = 2.20 +/- A 0.18 mu M) and 5-florouracil (IC50 = 2.30 +/- A 0.49 mu M). Structure activity relationship of synthesized analogs suggested that the presence of NH linker with aryl moiety at the third position of quinazolinone ring was important for potent anticancer activity. Electron donating group on phenyl ring at the third position of quinazolinone ring gave better anticancer activity then unsubstituted phenyl and electron withdrawing group. Activity by substituted piperazine at 2nd position of thiazole linked with quinazolinone scaffold gave better activity in the order of H > CH3 > CO-C6H5. Our findings may impart new direction to medicinal chemists and biochemists for further investigations of quinazolinone-thiazole containing anticancer agents.

  DOI：

  10.1007/s00044-012-0260-2