1-(2-thienylcarbonyl)-3-(4-aminosulfonylphenyl)thiourea | 443747-41-9

• 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-(2-thienylcarbonyl)-3-(4-aminosulfonylphenyl)thiourea
• 英文别名: N-((4-sulfamoylphenyl)carbamothioyl)thiophene-2-carboxamide；N-[4-sulfonamidephenyl]-N'-[2-thiophenoyl]thiourea；4-(Thiophene-2-carbonylcarbamothioylamino)benzenesulfonimidic acid；4-(thiophene-2-carbonylcarbamothioylamino)benzenesulfonimidic acid
• CAS: 443747-41-9
• 化学式: C₁₂H₁₁N₃O₃S₃
• 分子量: 341.436
• InChiKey: TVJDNPNVZCZHNV-UHFFFAOYSA-N

物化性质

• 密度：
  1.573±0.06 g/cm3(Predicted)
• 溶解度：
  6.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  170
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-噻吩甲酰氯 在 硫氰酸铵 作用下， 以 丙酮 为溶剂， 反应 2.25h， 生成 1-(2-thienylcarbonyl)-3-(4-aminosulfonylphenyl)thiourea
  参考文献：
  名称：

  Synthesis, Spectroscopic Characterization, Crystal structure, Antimicrobial and In Vitro Hemolytic Studies of Some Novel Substituted Thiourea Derivatives

  摘要：

  一系列 N,N′-二取代的硫脲类化合物，[R-CONHCSNH-R′] 其中（R = 噻吩基、呋喃基、苯基和 R′ = ；对 4-磺酰胺基苯基、嘧啶-2-基、噻唑-2-基、3-硝基苯基、2-硝基-4-氯苯基、2-氯-4-硝基苯基、2-甲氧基-4-硝基苯基和 6-苯基-1,3,5-三嗪基进行了合成、表征和抗菌活性筛选。通过元素分析和光谱技术（傅立叶变换红外光谱、1H NMR 和 13C NMR）确定了合成化合物的结构。对化合物 1a 和 1c 进行了单晶研究。化合物 1a 在单斜空间群 Cc 中结晶，a = 15.2974(5) 埃，b = 11.7766(4) 埃，c = 8.1059(3) 埃，α = 90°，β = 106.31(3)°，γ = 90°，Z = 每个单位晶胞有 4 个分子，而化合物 1c 在正方空间群 Pbca 中结晶，a = 7。6307(6) 埃，b = 11.3895(9) 埃，c = 24.121(2) 埃，α = β = γ = 90°，Z = 每单位晶胞 8 个分子。测试了所有化合物对四种人类病原菌和三种真菌菌株的抑制活性。筛选数据显示，五个化合物显示出中等至良好的活性，而其中一个化合物 1k 显示出极佳的活性。这些化合物的体外溶血活性表明它们是无毒的。通过元素分析、光谱技术（傅立叶变换红外光谱、1H NMR 和 13C NMR）和对其中两个化合物的单晶研究，合成了 11 个二取代的硫脲化合物，并对其进行了表征，以了解化合物的适当结构特征。对所有化合物都进行了抗菌活性筛选，其中两种化合物对所用细菌和真菌具有良好的抗菌活性。

  DOI：

  10.1007/s10870-013-0468-0

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.
• Synthesis, biological evaluation and docking study of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors
  作者：Mohammad Mahdavi、Maryam Shahzad Shirazi、Raana Taherkhani、Mina Saeedi、Eskandar Alipour、Farshad Homayouni Moghadam、Alireza Moradi、Hamid Nadri、Saeed Emami、Loghman Firoozpour、Abbas Shafiee、Alireza Foroumadi

  DOI：10.1016/j.ejmech.2014.05.054

  日期：2014.7

  A series of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives containing sulfonamide moiety were designed and synthesized as 15-lipoxygenase (15-LOX) inhibitors. Most synthesized compounds showed potent activity against soybean 15-LOX with IC50 values less than 25 mu M. The most potent compound 4c (3-methylbenzoyl derivative) with IC50 value of 1.8 mu M was 10-fold more potent than quercetin. Interestingly, compound 4c also showed the highest antioxidant activity, as determined by ferric reducing antioxidant power (FRAP) assay. Its capacity for reducing ferric ion was more than ascorbic acid. The viability assay of the selected compound 4c against oxidative stress-induced cell death in differentiated PC12 cells revealed that compound 4c significantly protected neurons against cell death in low concentrations. (C) 2014 Elsevier Masson SAS. All rights reserved.