2-({3-[(methylsulfonyl)amino]-4-oxo-6-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl}thio)benzoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-({3-[(methylsulfonyl)amino]-4-oxo-6-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl}thio)benzoic acid
• 英文别名: 2-[3-(Methanesulfonamido)-4-oxo-6-phenylthieno[2,3-d]pyrimidin-2-yl]sulfanylbenzoic acid
• 化学式: C₂₀H₁₅N₃O₅S₃
• 分子量: 473.554
• InChiKey: CWSHIEMMFHSFMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  178
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氨基-5-苯基噻吩-3-甲酸乙酯 在 sodium hydroxide 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 11.33h， 生成 2-({3-[(methylsulfonyl)amino]-4-oxo-6-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl}thio)benzoic acid
  参考文献：
  名称：

  由2-异硫氰酸根基-5-苯基-3-噻吩羧酸乙酯衍生的潜在选择性cox-2酶抑制剂的合成

  摘要：

  从2-异硫氰酸根合-5-苯基-3-噻吩羧酸的乙酯开始制备含有噻吩并[2,3 - d ]嘧啶-4-酮系统的衍生物，潜在的选择性COX-2抑制剂（2）；他们的结构阐明也有报道。

  DOI：

  10.1002/jhet.5570400519

文献信息

• Sulfonilamidothiopyrimidone and thiopyrimidone derivatives as selective COX-2 inhibitors: Synthesis, biological evaluation, and docking studies
  作者：Livia Basile、Susana Álvarez、Almudena Blanco、Andrea Santagati、Giuseppe Granata、Patrizia Di Pietro、Salvatore Guccione、Mª Ángeles Muñoz-Fernández

  DOI：10.1016/j.ejmech.2012.09.005

  日期：2012.11

  Newly synthesized sulfonilamidothiopyrimidone derivatives and a subset of 14 sulfonilamidothiopyrimidones and thiopyrimidones selected by an MTT assays cell viability guided selection from an in house collection were evaluated to determine the inhibitory effect on the PGE(2) formation in human peripheral blood lymphocytes (PBLs) using commercial ELISA. The newly synthesized sulfonilamidothiopyrimidone derivatives showed interesting pharmacological activities. Preliminary in vitro assays showed that compounds 2-5 are endowed with very high activity. Compound 2 was the most active as hCOX-2 inhibitor. The observed effects were not due to an inhibition of cell proliferation as proved by the BrdU assay. Western blot of COX-2 confirmed the inhibition on the PGE(2) secretion. Further evidence on the inhibitory potential and selectivity as COX-2 inhibitors of the selected compounds came from the in vitro screening. In order to better rationalize the action and the binding mode of these compounds, docking studies were carried out. These studies were in agreement with the biological data. Compounds 2-5 were able to fit into the active site of COX-2 with highest scores and interaction energies. Furthermore, compound 2, which showed an inhibition of around 50% on PGE(2) production, was the best scored in all the docking calculations carried out. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of potential selective cox-2 enzyme inhibitors derived from ethyl ester of 2-isothiocyanato-5-phenyl-3-thiophenecarboxylic acid
  作者：Andrea Santagati、Agostino Marrazzo、Giuseppe Granata

  DOI：10.1002/jhet.5570400519

  日期：2003.9

  Derivatives containing the thieno[2,3-d]pyrimidin-4-one system, potential selective COX-2 inhibitors, were prepared starting from ethyl ester of 2-isothiocyanato-5-phenyl-3-thiophenecarboxylic acid (2); their structural elucidation is also reported.

  从2-异硫氰酸根合-5-苯基-3-噻吩羧酸的乙酯开始制备含有噻吩并[2,3 - d ]嘧啶-4-酮系统的衍生物，潜在的选择性COX-2抑制剂（2）；他们的结构阐明也有报道。