6-bromo-3-(1,1-dioxido-3,4-dihydro-2H-1,2,4-benzothiadiazin-3-yl)-4H-chromen-4-one | 1263482-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 6-bromo-3-(1,1-dioxido-3,4-dihydro-2H-1,2,4-benzothiadiazin-3-yl)-4H-chromen-4-one
• 英文别名: 6-bromo-3-(1,1-dioxo-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazin-3-yl)chromen-4-one；6-bromo-3-(1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazin-3-yl)chromen-4-one
• CAS: 1263482-49-0
• 化学式: C₁₆H₁₁BrN₂O₄S
• 分子量: 407.244
• InChiKey: HIXBINVVCDSEHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-溴-3-甲酰色酮 、 邻氨基苯磺酰胺 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 以77%的产率得到6-bromo-3-(1,1-dioxido-3,4-dihydro-2H-1,2,4-benzothiadiazin-3-yl)-4H-chromen-4-one
  参考文献：
  名称：

  Identification of novel chromone based sulfonamides as highly potent and selective inhibitors of alkaline phosphatases

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.06.015

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.