3-amino-2-[(2,4-dinitrophenyl)thio]-6-phenylthieno[2,3-d]pyrimidin-4(3H)-one | 1144853-42-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-amino-2-[(2,4-dinitrophenyl)thio]-6-phenylthieno[2,3-d]pyrimidin-4(3H)-one
• 英文别名: 3-Amino-2-(2,4-dinitrophenyl)sulfanyl-6-phenylthieno[2,3-d]pyrimidin-4-one
• CAS: 1144853-42-8
• 化学式: C₁₈H₁₁N₅O₅S₂
• 分子量: 441.448
• InChiKey: DGJPGAWQJDNZBQ-UHFFFAOYSA-N

物化性质

• 熔点：
  213-215 °C (decomp)
• 沸点：
  701.1±70.0 °C(predicted)
• 密度：
  1.71±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  204
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,4-二硝基碘苯 、 3-amino-2,3-dihydro-6-phenyl-2-thioxothieno[2,3-d]pyrimidin-4(1H)-one sodium salt 在 铜 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以40%的产率得到3-amino-2-[(2,4-dinitrophenyl)thio]-6-phenylthieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Inhibition of iNOS and COX-2 in human whole blood ex vivo and monocyte-macrophage J774 cells by a new group of aminothiopyrimidone derivatives

  摘要：

  We tested a series of 11 new aminothiopyrimidones on the activity of inducible nitric oxide synthase (iNOS) and prostaglandin G/H synthase-1 and 2 (COX-1 and COX-2) in the whole human blood and monocyte-macrophage J774 cell line. To induce COX-2 and iNOS, blood samples and J774 cells were stimulated with bacterial lipopolysaccharide (LPS) in the absence or presence of the test compounds. After incubation, the plasma and the supernatants of culture media were collected for the measurement of TxB(2) and PGE(2) by a specific enzyme-immunoassay and determination of nitrite by a colorimetric assay. Several phenylthieno derivatives of substituted pyrimidone inhibited formation of both COX-2 and iNOS derived products with one of the compounds (compound 11, N-[2-[(2,4-dinitrophenyl)thio]-4-oxo-6-phenylthieno[2,3-d]pyrimidin-3(4H)-y]methanesulfonamide) showing a complete inhibition of LPS-stimulated formation of NO and PGE(2). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.029

文献信息

• Inhibition of iNOS and COX-2 in human whole blood ex vivo and monocyte-macrophage J774 cells by a new group of aminothiopyrimidone derivatives
  作者：Venera Cardile、Laura Lombardo、Giuseppe Granata、Antonio Perdicaro、Michael Balazy、Andrea Santagati

  DOI：10.1016/j.bmc.2009.01.029

  日期：2009.3

  We tested a series of 11 new aminothiopyrimidones on the activity of inducible nitric oxide synthase (iNOS) and prostaglandin G/H synthase-1 and 2 (COX-1 and COX-2) in the whole human blood and monocyte-macrophage J774 cell line. To induce COX-2 and iNOS, blood samples and J774 cells were stimulated with bacterial lipopolysaccharide (LPS) in the absence or presence of the test compounds. After incubation, the plasma and the supernatants of culture media were collected for the measurement of TxB(2) and PGE(2) by a specific enzyme-immunoassay and determination of nitrite by a colorimetric assay. Several phenylthieno derivatives of substituted pyrimidone inhibited formation of both COX-2 and iNOS derived products with one of the compounds (compound 11, N-[2-[(2,4-dinitrophenyl)thio]-4-oxo-6-phenylthieno[2,3-d]pyrimidin-3(4H)-y]methanesulfonamide) showing a complete inhibition of LPS-stimulated formation of NO and PGE(2). (C) 2009 Elsevier Ltd. All rights reserved.