2-{[(6-ethyl-2-ethoxy-4-oxo-2H-chromen-3(4H)-ylidene)methyl]amino}benzenesulfonamide | 1449215-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-{[(6-ethyl-2-ethoxy-4-oxo-2H-chromen-3(4H)-ylidene)methyl]amino}benzenesulfonamide
• CAS: 1449215-84-2
• 化学式: C₂₀H₂₂N₂O₅S
• 分子量: 402.471
• InChiKey: ZLJRMTWDBIMQHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  107.72
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  6-乙基-3-甲酰基色酮 、 乙醇 、 邻氨基苯磺酰胺 反应 3.0h， 生成 2-{[(6-ethyl-2-ethoxy-4-oxo-2H-chromen-3(4H)-ylidene)methyl]amino}benzenesulfonamide
  参考文献：
  名称：

  2-烷氧基-3-（磺酰基芳基氨基亚甲基）-苯并吡喃-4-酮类是外切核苷酸酶的强效和选择性抑制剂

  摘要：

  已经开发了一种用于调节3-甲酰基色酮烯胺的2-烷氧基侧链的简便方法来合成一系列2-烷氧基-3-（磺酰基芳基氨基亚甲基）-苯并吡喃-4-酮。通过简单地将醇反应介质从甲醇更改为乙醇，异丙醇和正丁醇，同时使各种3-甲酰基色酮与氨基苯磺酰胺反应，即可实现这种调节。醇具有足够的亲核性，可加入3-甲酰基色酮的C2-C3烯烃键中，而不会引起环裂解。发现所得的2-烷氧基-3-（磺酰基芳基氨基亚甲基）-苯并吡喃-4-酮是有效的和选择性的ecto-5′-核苷酸酶和碱性磷酸酶抑制剂（TNAP和IAP）。详细的酶动力学研究表明，对碱性磷酸酶具有竞争性抑制作用，而对大鼠和人ecto-5'-核苷酸酶则具有非竞争性抑制作用。最具活性的TNAP抑制剂23（K i  = 0.078±0.001μM），对TNAP的选择性是IAP（K i  = 2.18± 0.12μM）的28倍。化合物9是最具活性的IAP抑制剂（K i  =

  DOI：

  10.1016/j.ejmech.2016.02.073

文献信息

• Identification of novel chromone based sulfonamides as highly potent and selective inhibitors of alkaline phosphatases
  作者：Mariya al-Rashida、Rabia Raza、Ghulam Abbas、Muhammad Shakil Shah、George E. Kostakis、Joanna Lecka、Jean Sévigny、Muhammad Muddassar、Constantina Papatriantafyllopoulou、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2013.06.015

  日期：2013.8

  A new series of structurally diverse chromone containing sulfonamides has been developed. Crystal structures of three representative compounds (2a, 3a and 4a) in the series are reported. All compounds were screened for their inhibitory potential against alkaline phosphatases (ALPs). Two main classes of ALP isozymes were selected for this study, the tissue non-specific alkaline phosphatase (TNALP) from bovine and porcine source and the tissue-specific intestinal alkaline phosphatases (IALPs) from bovine source. All sulfonamide compounds had a marked preference for IALP (K-i, up to 0.01 +/- 0.001 mu M) over TNALPs. Kinetics studies of the compounds showed competitive mode of inhibition. Molecular docking studies were carried out in order to characterize the selective inhibition of the compounds. An additional interesting aspect of these chromone sulfonamides is their inhibitory activity against ecto-5'-nucleotidase enzyme. (C) 2013 Elsevier Masson SAS. All rights reserved.