1-(oxo-2H-chromene-3-carbonyl)-3-(3-aminosulfonylphenyl)thiourea | 1606167-42-3

• 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: 1-(oxo-2H-chromene-3-carbonyl)-3-(3-aminosulfonylphenyl)thiourea
• 英文别名: 2-oxo-N-[(3-sulfamoylphenyl)carbamothioyl]chromene-3-carboxamide
• CAS: 1606167-42-3
• 化学式: C₁₇H₁₃N₃O₅S₂
• 分子量: 403.439
• InChiKey: OVKWYKQJPMYNJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  香豆素-3-甲酰氯 以 乙腈 为溶剂， 反应 0.5h， 生成 1-(oxo-2H-chromene-3-carbonyl)-3-(3-aminosulfonylphenyl)thiourea
  参考文献：
  名称：

  New aminobenzenesulfonamide–thiourea conjugates: Synthesis and carbonic anhydrase inhibition and docking studies

  摘要：

  A variety of 1-substituted-3-(3-aminosulfonylphenyl)thioureas (3a-k) and two new 1-aroyl-3-(4-aminosulfonylphenyl)thiourea derivatives (5a and 5b) were synthesized by reaction of 3-aminobenzenesulfonamide and 4-aminobenzenesulfonamide respectively with freshly prepared aroyl/heteroaryl isothiocyanates in dry acetonitrile. FTIR, H-1 NMR, C-13 NMR, GC-MS and elemental analyses data confirmed the assigned structures to the synthesized compounds. Further structure of compound (3g) was also confirmed by single crystal XRD analysis. The compounds were investigated as inhibitors of the bovine erythrocyte carbonic anhydrase isoform II (bCA II). The inhibition constants of these compounds against bCA II were in the range 0.011-17.1 mu M. Among the evaluated compounds, 1-substituted -3-(3-aminosulfonylphenyl)thiourea derivatives 3h and 5a were the most potent inhibitors with IC50 of 0.052 and 0.011 mu M, respectively. In silico docking and molecular dynamics simulation studies were performed against bCA II and human CA II enzymes to rationalize the inhibitory properties of these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.023

文献信息

• New aminobenzenesulfonamide–thiourea conjugates: Synthesis and carbonic anhydrase inhibition and docking studies
  作者：Sumera Zaib、Aamer Saeed、Karin Stolte、Ulrich Flörke、Mohammad Shahid、Jamshed Iqbal

  DOI：10.1016/j.ejmech.2014.03.023

  日期：2014.5

  A variety of 1-substituted-3-(3-aminosulfonylphenyl)thioureas (3a-k) and two new 1-aroyl-3-(4-aminosulfonylphenyl)thiourea derivatives (5a and 5b) were synthesized by reaction of 3-aminobenzenesulfonamide and 4-aminobenzenesulfonamide respectively with freshly prepared aroyl/heteroaryl isothiocyanates in dry acetonitrile. FTIR, H-1 NMR, C-13 NMR, GC-MS and elemental analyses data confirmed the assigned structures to the synthesized compounds. Further structure of compound (3g) was also confirmed by single crystal XRD analysis. The compounds were investigated as inhibitors of the bovine erythrocyte carbonic anhydrase isoform II (bCA II). The inhibition constants of these compounds against bCA II were in the range 0.011-17.1 mu M. Among the evaluated compounds, 1-substituted -3-(3-aminosulfonylphenyl)thiourea derivatives 3h and 5a were the most potent inhibitors with IC50 of 0.052 and 0.011 mu M, respectively. In silico docking and molecular dynamics simulation studies were performed against bCA II and human CA II enzymes to rationalize the inhibitory properties of these compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.