4-azido-N-(4-methylpyrimidin-2-yl)benzenesulfonamide | 88609-05-6

• 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-azido-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
• CAS: 88609-05-6
• 化学式: C₁₁H₁₀N₆O₂S
• 分子量: 290.305
• InChiKey: GTXMBVUMAJNIER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  94.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-azido-N-(4-methylpyrimidin-2-yl)benzenesulfonamide 、 2-propynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 以60%的产率得到4-{4-[(2’,3’,4’,6’-tetra-O-acetyl-β-D-galactopyranosyl)oxymethyl]-1H-1,2,3-triazol-1-yl}-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis andin vitroEvaluation of Novel Galactosyl-triazolo-benzenesulfonamides AgainstTrypanosoma cruzi

  摘要：

  The only drugs approved for the treatment of Chagas disease, nifurtimox and benznidazole, present toxic side effects and limited efficacy in the chronic stage of the disease, which highlight the need for new drugs. Amongst the different molecular drug targets discovered in the parasite, Trypanosoma cruzi trans-sialidase (TcTS) has been considered crucial in the recognition and invasion of host cells. Hence, we report the efficient synthesis and biological evaluation (TcTS inhibition and antitrypanosomal activities) of some galactose-containing triazol-arylsulfonamides via microwave-assisted Cu(I) 1,3-dipolar azide-alkyne cycloaddition (CuAAC) based on azide benzenesulfonamides and a galactose-derived alkyne as precursors. Most of the compounds tested against TcTS showed moderate to weak inhibition (40%-15%), except one of the compounds (81%). Regarding the antitrypanosomal assay, some compounds [(IC50 70.9 mu M) and (IC50 44.0 mu M)] exhibited the most significant activities, although not as active as benznidazole (IC50 1.4 mu M). Nevertheless, the cytotoxicity assessment showed that all compounds were not cytotoxic. In this preliminary work, we considered some compounds as lead scaffolds for further optimization.

  DOI：

  10.5935/0103-5053.20140158
• 作为产物：
  描述：

  磺胺甲基嘧啶 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 水 为溶剂， 反应 0.25h， 以80%的产率得到4-azido-N-(4-methylpyrimidin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  新型 1,4-二取代-1,2,3-三唑胸腺嘧啶衍生物的点击合成、分子对接、对乳腺癌的细胞毒性 (MDA-MB 231) 和抗 HIV 活性

  摘要：

  摘要 合成了一系列新的 1,4-二取代-1,2,3-三唑胸腺嘧啶衍生物 (VIa – e)，并通过光谱研究对其进行了表征。通过 MTT 测定评估所选化合物对人癌细胞系 (MDA-MB 231) 的体外细胞毒活性。4-叠氮基-N-取代的苯磺酰胺 (Vc – e ) 和 4,4'-(4,4'-((5-methyl-2,4-dioxopyrimidine-1,3(2 H ,4 H )-diyl )双(亚甲基))-双(1H-1,2,3-三唑-4,1-二基))-双(N-(4-甲基嘧啶-2-基)苯磺酰胺)(VIc)显示出显着的细胞毒活性，IC 50 值分别为 1.61、1.41、1.61 和 1.81 μM。4-叠氮基-N-(4,6-二甲基嘧啶-2-基)苯磺酰胺(Vd)和4,4'-(4,4'-((5-methyl-2,4-dioxopyrimidine-1))的分子对接研究,3(2 H ,4 H )-二基)双(亚甲基))-双(1

  DOI：

  10.1134/s1068162020030024

文献信息

• Binding of triazole-linked galactosyl arylsulfonamides to galectin-3 affects Trypanosoma cruzi cell invasion
  作者：Marcelo Fiori Marchiori、Thalita B. Riul、Leandro Oliveira Bortot、Peterson Andrade、Getúlio G. Junqueira、Giuseppina Foca、Nunzianna Doti、Menotti Ruvo、Marcelo Dias-Baruffi、Ivone Carvalho、Vanessa Leiria Campo

  DOI：10.1016/j.bmc.2017.09.042

  日期：2017.11

  The synthesis of the O-3 triazole-linked galactosyl arylsulfonamides 1–7 as potential inhibitors of Trypanosoma cruzi cell invasion is described. These target compounds were synthesized by Cu(I)-catalysed azide-alkyne cycloaddition reaction (‘click chemistry’) between different azide arylsulfonamides and the alkyne-based sugar 3-O-propynyl-βGalOMe. Inhibition assays of T. cruzi cell invasion with compounds

  的O-3三唑连接的半乳糖基芳基磺酰胺的合成1 - 7作为潜在抑制剂克氏锥虫细胞侵袭进行说明。这些目标化合物是通过Cu（I）催化的叠氮化物-芳基磺酰胺与炔烃基糖3-O-丙炔基-βGalOMe之间的叠氮化物-炔烃环加成反应（“点击化学”）合成的。用化合物1 – 7侵染克氏锥虫细胞的抑制试验表明，化合物3和5带有相应的5-甲基异恶唑和2,4-二甲氧基嘧啶基团，其感染指数降低（〜20），并且对化合物的结合亲和力更高。 galectin-3（EC50 17–18μM）在康宁Epic无标签测定中。与实验结果一致，理论化合物的结合的评估1 - 7由MM / PBSA方法半乳凝素3显示更高亲和性的化合物3（-9.7千卡/摩尔）和5（-11.1千卡/摩尔）。总体而言，这些成就突出了化合物3和5通过半乳糖凝集素3结合相关的机制作为潜在的克鲁氏酵母细胞入侵阻滞剂的作用，揭示了半乳糖凝集素3作为设计新型抗锥虫病药物的重要宿主靶标。
• Rational Design and Synthesis of New Selective COX-2 Inhibitors with In Vivo PGE2-Lowering Activity by Tethering Benzenesulfonamide and 1,2,3-Triazole Pharmacophores to Some NSAIDs
  作者：Nada H. El-Dershaby、Soad A. El-Hawash、Shaymaa E. Kassab、Hoda G. Daabees、Ahmed E. Abdel Moneim、Mostafa M. M. El-Miligy

  DOI：10.3390/ph15101165

  日期：——

  New selective COX-2 inhibitors were designed and synthesized by tethering 1,2,3-triazole and benzenesulfonamide pharmacophores to some NSAIDs. Compounds 6b and 6j showed higher in vitro COX-2 selectivity and inhibitory activity (IC50 = 0.04 µM and S.I. = 329 and 312, respectively) than celecoxib (IC50 = 0.05 µM and S.I. = 294). Compound 6e revealed equipotent in vitro COX-2 inhibitory activity to celecoxib

  通过将 1,2,3-三唑和苯磺酰胺药效团与一些 NSAID 结合，设计和合成了新的选择性 COX-2 抑制剂。化合物6b和6j显示出比塞来昔布更高的体外 COX-2 选择性和抑制活性（IC 50 = 0.04 µM 和 SI = 329 和 312）（IC 50 = 0.05 µM 和 SI = 294）。化合物6e对塞来昔布具有等效的体外 COX-2 抑制活性。此外，与塞来昔布相比， 6b和6j对角叉菜胶诱导的小鼠爪水肿厚度的缓解作用更有效，ED 50值分别为 11.74 µmol/kg 和 13.38 µmol/kg 对 16.24 µmol/kg。化合物图6b和6j分别以90.70%和86.34%的抑制PGE2产生的百分比抑制PGE2的产生，超过塞来昔布的百分比（78.62%）。此外，6b和6j显示出与塞来昔布相当的胃安全性特征。总之，化合物6b和6j作为比塞来昔布在体外和体内更有效和选择性更强的
• Brown, Thomas B.; Lowe, Philip R.; Schwalbe, Carl H., Journal of the Chemical Society. Perkin transactions I, 1983, # 10, p. 2485 - 2490
  作者：Brown, Thomas B.、Lowe, Philip R.、Schwalbe, Carl H.、Stevens, Malcolm F.G.

  DOI：——

  日期：——
• A Click Synthesis, Molecular Docking, Cytotoxicity on Breast Cancer (MDA-MB 231) and Anti-HIV Activities of New 1,4-Disubstituted-1,2,3-Triazole Thymine Derivatives
  作者：Faeza Abdul Kareem Almashal、Hamsa Hussein Al-Hujaj、Ahmed Majeed Jassem、Najim Aboud Al-Masoudi

  DOI：10.1134/s1068162020030024

  日期：2020.5

  Molecular docking study of 4‑azido- N -(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide ( Vd ) and 4,4'-(4,4'-((5-methyl-2,4-dioxopyrimidine-1,3(2 H ,4 H )-diyl)bis(methylene))-bis(1 H -1,2,3-triazole-4,1-diyl))-bis ( N -(4-methyl pyrimidin-2-yl)benzenesulfonamide) ( VIc ) showed hydrogen bonding with the amino acid residues of the receptors 1X7R and 1A53, respectively. These derivatives are useful as starting

  摘要 合成了一系列新的 1,4-二取代-1,2,3-三唑胸腺嘧啶衍生物 (VIa – e)，并通过光谱研究对其进行了表征。通过 MTT 测定评估所选化合物对人癌细胞系 (MDA-MB 231) 的体外细胞毒活性。4-叠氮基-N-取代的苯磺酰胺 (Vc – e ) 和 4,4'-(4,4'-((5-methyl-2,4-dioxopyrimidine-1,3(2 H ,4 H )-diyl )双(亚甲基))-双(1H-1,2,3-三唑-4,1-二基))-双(N-(4-甲基嘧啶-2-基)苯磺酰胺)(VIc)显示出显着的细胞毒活性，IC 50 值分别为 1.61、1.41、1.61 和 1.81 μM。4-叠氮基-N-(4,6-二甲基嘧啶-2-基)苯磺酰胺(Vd)和4,4'-(4,4'-((5-methyl-2,4-dioxopyrimidine-1))的分子对接研究,3(2 H ,4 H )-二基)双(亚甲基))-双(1
• Synthesis and<i>in vitro</i>Evaluation of Novel Galactosyl-triazolo-benzenesulfonamides Against<i>Trypanosoma cruzi</i>
  作者：Getúlio G. Junqueira、Marcelo R. Carvalho、Peterson de Andrade、Carla D. Lopes、Zumira A. Carneiro、Renata Sesti-Costa、João S. Silva、Ivone Carvalho

  DOI：10.5935/0103-5053.20140158

  日期：——

  The only drugs approved for the treatment of Chagas disease, nifurtimox and benznidazole, present toxic side effects and limited efficacy in the chronic stage of the disease, which highlight the need for new drugs. Amongst the different molecular drug targets discovered in the parasite, Trypanosoma cruzi trans-sialidase (TcTS) has been considered crucial in the recognition and invasion of host cells. Hence, we report the efficient synthesis and biological evaluation (TcTS inhibition and antitrypanosomal activities) of some galactose-containing triazol-arylsulfonamides via microwave-assisted Cu(I) 1,3-dipolar azide-alkyne cycloaddition (CuAAC) based on azide benzenesulfonamides and a galactose-derived alkyne as precursors. Most of the compounds tested against TcTS showed moderate to weak inhibition (40%-15%), except one of the compounds (81%). Regarding the antitrypanosomal assay, some compounds [(IC50 70.9 mu M) and (IC50 44.0 mu M)] exhibited the most significant activities, although not as active as benznidazole (IC50 1.4 mu M). Nevertheless, the cytotoxicity assessment showed that all compounds were not cytotoxic. In this preliminary work, we considered some compounds as lead scaffolds for further optimization.