4-{[(4-methyl-6-oxo-1,6-dihydro-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide | 1376685-61-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-{[(4-methyl-6-oxo-1,6-dihydro-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide
• 英文别名: 4-{[(4-Methyl-6-Oxo-1,6-Dihydropyrimidin-2-Yl)sulfanyl]acetyl}benzenesulfonamide；4-[2-[(4-methyl-6-oxo-1H-pyrimidin-2-yl)sulfanyl]acetyl]benzenesulfonamide
• CAS: 1376685-61-8
• 化学式: C₁₃H₁₃N₃O₄S₂
• 分子量: 339.396
• InChiKey: UZGWPPSMIYIVBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲基硫脲嘧啶 、 4-(2-bromoacetyl)benzenesulfonamide 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以75%的产率得到4-{[(4-methyl-6-oxo-1,6-dihydro-2-pyrimidinyl)sulfanyl]acetyl}benzenesulfonamide
  参考文献：
  名称：

  Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases

  摘要：

  A series of [(2-pyrimidinylthio)acetyl]benzenesulfonamides were designed and synthesized. Their binding affinities as inhibitors of several recombinant human carbonic anhydrase (CA) isozymes were determined by isothermal titration calorimetry (ITC) and thermal shift assay (TSA). A group of compounds containing a chlorine atom in the benzenesulfonamide ring were found to exhibit higher selectivity but lower binding affinity toward tested CAs. The crystal structures of selected compounds in complex with CA II were determined to atomic resolution. Docking studies were performed to compare the binding modes of experimentally determined crystallographic structures with computational prediction of the pyrimidine derivative binding to CA II. Several compounds bound to select CAs with single-digit nanomolar affinities and could be used as leads for inhibitor development toward a select CA isozyme. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.050

文献信息

• Design of [(2-pyrimidinylthio)acetyl]benzenesulfonamides as inhibitors of human carbonic anhydrases
  作者：Edita Čapkauskaitė、Asta Zubrienė、Lina Baranauskienė、Giedrė Tamulaitienė、Elena Manakova、Visvaldas Kairys、Saulius Gražulis、Sigitas Tumkevičius、Daumantas Matulis

  DOI：10.1016/j.ejmech.2012.02.050

  日期：2012.5

  A series of [(2-pyrimidinylthio)acetyl]benzenesulfonamides were designed and synthesized. Their binding affinities as inhibitors of several recombinant human carbonic anhydrase (CA) isozymes were determined by isothermal titration calorimetry (ITC) and thermal shift assay (TSA). A group of compounds containing a chlorine atom in the benzenesulfonamide ring were found to exhibit higher selectivity but lower binding affinity toward tested CAs. The crystal structures of selected compounds in complex with CA II were determined to atomic resolution. Docking studies were performed to compare the binding modes of experimentally determined crystallographic structures with computational prediction of the pyrimidine derivative binding to CA II. Several compounds bound to select CAs with single-digit nanomolar affinities and could be used as leads for inhibitor development toward a select CA isozyme. (C) 2012 Elsevier Masson SAS. All rights reserved.