2-[(3-Methyl-2-oxo-[1,2,4]triazino[2,3-c]quinazolin-6-yl)sulfanyl]acetic acid | 1147760-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-[(3-Methyl-2-oxo-[1,2,4]triazino[2,3-c]quinazolin-6-yl)sulfanyl]acetic acid
• CAS: 1147760-51-7
• 化学式: C₁₃H₁₀N₄O₃S
• 分子量: 302.313
• InChiKey: SGLPRYZKAOKAIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(3-Methyl-2-oxo-[1,2,4]triazino[2,3-c]quinazolin-6-yl)sulfanyl]acetic acid 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 N-phenyl-2-[(2-oxo-3-methyl-2H-[1,2,4]triazino[2,3-c]quinazolin-6-yl)thio]acetamide
  参考文献：
  名称：

  Novel N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides: synthesis, cytotoxicity, anticancer activity, COMPARE analysis and docking

  摘要：

  The series of novel N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides were obtained by aminolysis of activated acids 1a-1d and by alkylation of potassium salts 2a-2d by N -aryl-2-chloroacetamies. The structures of compounds were determined by IR, H-1, C-13 NMR, LC- and EI-MS analyses. The results of cytotoxicity evaluation by bioluminescence inhibition of bacterium Photobacterium leiognathi Sh1 showed that compounds reveal moderate cytotoxicity. Screening of anticancer activity in vitro yielded the most active compounds 3t, 4b, 4f, 4l and 4n in micromolar concentrations with the GI(50) level (logGI(50) is from -7.57 to -4.05 for different cell lines, and logGI(50) mean graph midpoint varied from -5.30 to -4.50). Moreover, compound 4b had a distinctive selectivity against renal cancer, 4f-colon cancer and melanoma and 4l-renal cancer. The highest sensitivity to compound 4b showed renal cancer cell lines A498 (logGI(50) = -7.57). SAR-analysis was discussed, COMPARE analysis and docking was studied.The novel synthesis methods of the N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides are proposed. Anticancer activity and Photobacterium leiognathi Sh1 bioluminescence inhibition of synthesized compounds are discussed. SAR-analysis was discussed, and COMPARE analysis and docking was studied.

  DOI：

  10.1007/s00044-012-0257-x
• 作为产物：
  描述：

  6-methyl-3-(2-aminophenyl)-[1,2,4]-triazin-5-one 在 potassium hydroxide 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 生成 2-[(3-Methyl-2-oxo-[1,2,4]triazino[2,3-c]quinazolin-6-yl)sulfanyl]acetic acid
  参考文献：
  名称：

  新型N-环烷基-（环烷基芳基）-2-[（3-R-2-oxo-2 H- [1,2,4]三嗪[2,3 - c ]喹唑啉-6-基）的合成及生物活性硫代]乙酰胺

  摘要：

  本文中的新型N-环烷基-（环烷基芳基）-2-[（3-R-2-oxo-2 H- [1,2,4]三嗪[2,3 - c ]喹唑啉-6-基）硫基通过亚硫酰氯或羰基二咪唑[[3-R-2-oxo-2 H- [1,2,4]三嗪基[2,3 - c ]喹唑啉-6-基）-硫代]乙酸活化的酰胺水解合成乙酰胺酸和3-R-6-硫代-6,7-二氢-2 H- [1,2,4]三嗪基[2,3 - c ]喹唑啉-2-酮钾盐与N-环烷基-（提出了环烷基芳基）-2-氯乙酰胺。化合物的结构通过1 H，13 C NMR，LC-MS和EI-MS分析确定。在体外揭示了合成化合物的抗癌，抗菌活性和Leiognathi Sh1细菌对生物发光的抑制作用。讨论了SAR结果。化合物4。发现10是最具抗癌活性的化合物，对非小细胞肺癌和中枢神经系统癌细胞系有选择性的影响，特别是对HOP-92（log GI 50  = -6.01）和U251（log GI

  DOI：

  10.1016/j.ejmech.2011.10.022