4-(4,6-bis(3-aminopropylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide | 1571074-20-8

• 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: 4-(4,6-bis(3-aminopropylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide
• 英文别名: 4-[[4,6-Bis(3-aminopropylamino)-1,3,5-triazin-2-yl]amino]benzenesulfonamide；4-[[4,6-bis(3-aminopropylamino)-1,3,5-triazin-2-yl]amino]benzenesulfonamide
• CAS: 1571074-20-8
• 化学式: C₁₅H₂₅N₉O₂S
• 分子量: 395.489
• InChiKey: HJIJLILNIAUPQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  195
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  磺胺 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 生成 4-(4,6-bis(3-aminopropylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide
  参考文献：
  名称：

  Substituted benzene sulfonamides incorporating 1,3,5-triazinyl moieties potently inhibit human carbonic anhydrases II, IX and XII

  摘要：

  A series of benzene sulfonamides incorporating 1,3,5-triazinyl moieties were synthesized using cyanuric chloride as starting material. Inhibition studies against human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II (cytosolic) and IX, XII (transmembrane, tumor-associated) isoforms were performed with the new compounds. hCA I was modestly inhibited (K(I)s in the range of 87 nM-4.35 mu M), hCA II was moderately inhibited by most of the new compounds (K(I)s in the range of 12.5-130 nM), whereas the tumor associated isoforms were potently inhibited, with K(I)s in the range of 1.2-34.1 nM against hCA IX and of 2.1-33.9 against hCA XII, respectively. Docking studies of some of the new compounds showed an effective binding mode within the enzyme active site, as demonstrated earlier by X-ray crystallography for structurally-related sulfonamides incorporating 1,3,5-triazinyl functionalities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.048

文献信息

• Substituted benzene sulfonamides incorporating 1,3,5-triazinyl moieties potently inhibit human carbonic anhydrases II, IX and XII
  作者：Amrita K. Saluja、Meena Tiwari、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2014.01.048

  日期：2014.3

  A series of benzene sulfonamides incorporating 1,3,5-triazinyl moieties were synthesized using cyanuric chloride as starting material. Inhibition studies against human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II (cytosolic) and IX, XII (transmembrane, tumor-associated) isoforms were performed with the new compounds. hCA I was modestly inhibited (K(I)s in the range of 87 nM-4.35 mu M), hCA II was moderately inhibited by most of the new compounds (K(I)s in the range of 12.5-130 nM), whereas the tumor associated isoforms were potently inhibited, with K(I)s in the range of 1.2-34.1 nM against hCA IX and of 2.1-33.9 against hCA XII, respectively. Docking studies of some of the new compounds showed an effective binding mode within the enzyme active site, as demonstrated earlier by X-ray crystallography for structurally-related sulfonamides incorporating 1,3,5-triazinyl functionalities. (C) 2014 Elsevier Ltd. All rights reserved.