1-(4-chlorobenzoyl)-3-(3-aminosulfonylphenyl)thiourea | 1402241-13-7

• 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-(4-chlorobenzoyl)-3-(3-aminosulfonylphenyl)thiourea
• 英文别名: 4-chloro-N-[(3-sulfamoylphenyl)carbamothioyl]benzamide
• CAS: 1402241-13-7
• 化学式: C₁₄H₁₂ClN₃O₃S₂
• 分子量: 369.853
• InChiKey: DVJVCYXKDBNYTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 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：
  142
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰氯 以 丙酮 为溶剂， 反应 1.5h， 生成 1-(4-chlorobenzoyl)-3-(3-aminosulfonylphenyl)thiourea
  参考文献：
  名称：

  掺入酰基硫脲部分的3-氨基苯磺酰胺比脱靶同工型I，II和IV选择性抑制与肿瘤相关的碳酸酐酶同工型IX

  摘要：

  我们描述了一系列新型的1-芳酰基/酰基-3-（3-氨基磺酰基苯基）硫脲（4a-k）的合成，它们充当人类碳酸酐酶（hCA，EC 4.2.1.1）的抑制剂。烷基/芳基异硫氰酸酯与3-氨基苯磺酰胺的反应提供了一系列标题化合物，其结合了各种短的和高度亲脂的长尾巴。针对4种生理相关的CA同工型（hCA I，II，IV和IX）评估了新合成的磺酰胺。几种化合物表现出令人感兴趣的抑制活性。肿瘤相关的hCA IX是抑制这些化合物的最敏感同工型，K Is在21.5-44.0 nM范围内，对主要胞质亚型hCA II的选择性比在3.35-37.3范围内。结合了苯基乙酰基硫脲基和十五烷酰基硫脲基的磺酰胺是这项工作中检测到​​的最多的hCA IX选择性抑制剂，因此值得进一步研究。

  DOI：

  10.1016/j.bioorg.2018.10.006

文献信息

• Novel benzoyl thioureido benzene sulfonamides as highly potent and selective inhibitors of carbonic anhydrase IX: optimization and bioactive studies
  作者：Li Liu、Wanqi Wang、Jin Huang、Zhenjiang Zhao、Honglin Li、Yufang Xu

  DOI：10.1039/c8md00392k

  日期：——

  development of new anticancer agents. In this study, a series of sulfonamide derivatives were designed and synthesized as potential CA IX inhibitors from a lead compound (benzoyl thioureido benzene sulfonamide) discovered by virtual screening. The bioassay demonstrated that some of the synthesized compounds exhibited potent inhibitory activity against CA IX in the subnanomolar range and high selectivity over

  CA IX 作为开发新型抗癌药物的有前景的靶点而备受关注。在本研究中，通过虚拟筛选发现的先导化合物（苯甲酰基硫脲基苯磺酰胺）设计并合成了一系列磺酰胺衍生物作为潜在的 CA IX 抑制剂。生物测定表明，一些合成的化合物对亚纳摩尔范围内的 CA IX 表现出有效的抑制活性，并且对同工酶 CA I 和 CA II 具有高选择性。其中，化合物6a对CA IX表现出抑制活性，IC 50值为0.48 nM，选择性是CA II的约1500倍。还通过分子对接分析了新磺酰胺衍生物的构效关系和CA IX选择性。
• 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.
• 3-Aminobenzenesulfonamides incorporating acylthiourea moieties selectively inhibit the tumor-associated carbonic anhydrase isoform IX over the off-target isoforms I, II and IV
  作者：Tanzeela Abdul Fattah、Silvia Bua、Aamer Saeed、Ghulam Shabir、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2018.10.006

  日期：2019.2

  We describe the synthesis of a series of novel 1-aroyl/acyl-3-(3-aminosulfonylphenyl) thioureas (4a–k) acting as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. Reaction of alkyl/aryl isothiocyanates with 3-aminobenzenesulfonamide afforded a series of the title compounds incorporating a variety of short as well as highly lipophilic long tails. The newly synthesized sulfonamides were evaluated

  我们描述了一系列新型的1-芳酰基/酰基-3-（3-氨基磺酰基苯基）硫脲（4a-k）的合成，它们充当人类碳酸酐酶（hCA，EC 4.2.1.1）的抑制剂。烷基/芳基异硫氰酸酯与3-氨基苯磺酰胺的反应提供了一系列标题化合物，其结合了各种短的和高度亲脂的长尾巴。针对4种生理相关的CA同工型（hCA I，II，IV和IX）评估了新合成的磺酰胺。几种化合物表现出令人感兴趣的抑制活性。肿瘤相关的hCA IX是抑制这些化合物的最敏感同工型，K Is在21.5-44.0 nM范围内，对主要胞质亚型hCA II的选择性比在3.35-37.3范围内。结合了苯基乙酰基硫脲基和十五烷酰基硫脲基的磺酰胺是这项工作中检测到​​的最多的hCA IX选择性抑制剂，因此值得进一步研究。