8-methoxy-5,5-dioxo-6,6a-dihydrodipyrido[2,1-c:4',3'-e][1,2,4]thiadiazin-7-yl sulfonamide | 1335122-23-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 8-methoxy-5,5-dioxo-6,6a-dihydrodipyrido[2,1-c:4',3'-e][1,2,4]thiadiazin-7-yl sulfonamide
• 英文别名: 3-Methoxy-4a,6-dioxopyrido[1',2':4,3]pyrido[4,3-e][1,2,4]thiadiazine-4-sulfonamide；12-methoxy-8,8-dioxo-8λ6-thia-1,5,9-triazatricyclo[8.4.0.02,7]tetradeca-2(7),3,5,11,13-pentaene-11-sulfonamide
• CAS: 1335122-23-0
• 化学式: C₁₁H₁₂N₄O₅S₂
• 分子量: 344.372
• InChiKey: ZTDXINULRDONTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  甲醇 、 4-氯吡啶-3-磺酰胺 在 尿素 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以66%的产率得到8-methoxy-5,5-dioxo-6,6a-dihydrodipyrido[2,1-c:4',3'-e][1,2,4]thiadiazin-7-yl sulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Synthesis, molecular structures, and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with novel 3-pyridinesulfonamide derivatives

  摘要：

  A series of novel 3-pyridinesulfonamide derivatives (2-5, 9-11 and 13-15) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is, the cytosolic ubiquitous CA I and II, and isozymes CA IX and XII (cancer-associated), and XIV. Against the human isozyme hCA I the new compounds showed K(I)s in the range of 0.089-251 mu M, whereas toward hCA II, K(I)s = 50.5-487 nM. Isozyme hCA IX was inhibited with K(I)s in the range of 5.2-18.3 nM, while hCA XII with K(I)s = 6.0-16.4 nM, and hCA XIV with K(I)s = 76.4-152.0 nM. All of the new compounds 2-5,9-11 and 13-15 showed excellent hCA IX inhibitory efficacy, with Kis = 5.2-18.3 nM, being much more effective as compared to the clinically used AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.011

文献信息

• Carbonic anhydrase inhibitors. Synthesis, molecular structures, and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with novel 3-pyridinesulfonamide derivatives
  作者：Zdzisław Brzozowski、Jarosław Sławiński、Maria Gdaniec、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2011.07.011

  日期：2011.9

  A series of novel 3-pyridinesulfonamide derivatives (2-5, 9-11 and 13-15) have been synthesized and investigated as inhibitors of five isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), that is, the cytosolic ubiquitous CA I and II, and isozymes CA IX and XII (cancer-associated), and XIV. Against the human isozyme hCA I the new compounds showed K(I)s in the range of 0.089-251 mu M, whereas toward hCA II, K(I)s = 50.5-487 nM. Isozyme hCA IX was inhibited with K(I)s in the range of 5.2-18.3 nM, while hCA XII with K(I)s = 6.0-16.4 nM, and hCA XIV with K(I)s = 76.4-152.0 nM. All of the new compounds 2-5,9-11 and 13-15 showed excellent hCA IX inhibitory efficacy, with Kis = 5.2-18.3 nM, being much more effective as compared to the clinically used AAZ, MZA, EZA, DCP and IND (K(I)s = 24-50 nM). (C) 2011 Elsevier Masson SAS. All rights reserved.