N-(2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-7-yl)-4-nitrobenzamide | 20899-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-7-yl)-4-nitrobenzamide
• CAS: 20899-04-1
• 化学式: C₁₉H₁₀N₂O₆
• 分子量: 362.298
• InChiKey: DZFDNNYKMKLGKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-amino-naphthalene-1,8-dicarboxylic acid-anhydride 、 4-硝基苯甲酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 以68%的产率得到N-(2,4-dioxo-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-7-yl)-4-nitrobenzamide
  参考文献：
  名称：

  Ligand-based discovery of N-(1,3-dioxo-1H,3H-benzo[de]isochromen-5-yl)-carboxamide and sulfonamide derivatives as thymidylate synthase A inhibitors

  摘要：

  Phenolnaphthalein derivatives show potential for pharmacological activity as inhibitors of thymidylate synthase (TS) but difficulties in their synthesis and derivatization hinder their development. A deconstruction approach aimed at identifying a suitable new scaffold was proposed. A new scaffold was identified and two compound libraries based on this scaffold were designed. The carboxamide library ( Library B) showed specific inhibition activity against Escherichia coli TS, whereas the sulfonamide library ( Library C) showed a non-specific inhibition profile against hTS. N-(1,3-Dioxo-1H,3H-benzo[de] isochromen-5-yl)-sulfonamide derivatives, 1C and 9C, showed one order of magnitude improvement in inhibition constant against hTS with respect to the starting lead and represent potential compounds for further lead development. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.117

文献信息

• Ligand-based discovery of N-(1,3-dioxo-1H,3H-benzo[de]isochromen-5-yl)-carboxamide and sulfonamide derivatives as thymidylate synthase A inhibitors
  作者：Stefania Ferrari、Marco Ingrami、Fabrizia Soragni、Rebecca C. Wade、M. Paola Costi

  DOI：10.1016/j.bmcl.2012.11.117

  日期：2013.2

  Phenolnaphthalein derivatives show potential for pharmacological activity as inhibitors of thymidylate synthase (TS) but difficulties in their synthesis and derivatization hinder their development. A deconstruction approach aimed at identifying a suitable new scaffold was proposed. A new scaffold was identified and two compound libraries based on this scaffold were designed. The carboxamide library ( Library B) showed specific inhibition activity against Escherichia coli TS, whereas the sulfonamide library ( Library C) showed a non-specific inhibition profile against hTS. N-(1,3-Dioxo-1H,3H-benzo[de] isochromen-5-yl)-sulfonamide derivatives, 1C and 9C, showed one order of magnitude improvement in inhibition constant against hTS with respect to the starting lead and represent potential compounds for further lead development. (c) 2012 Elsevier Ltd. All rights reserved.