N-(1H-indazol-5-yl)-4-nitro-benzenesulfonamide | 1198747-63-5

• 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: N-(1H-indazol-5-yl)-4-nitro-benzenesulfonamide
• 英文别名: N-(1H-indazol-5-yl)-4-nitrobenzenesulfonamide
• CAS: 1198747-63-5
• 化学式: C₁₃H₁₀N₄O₄S
• 分子量: 318.313
• InChiKey: ALZQGHRYVMAIDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 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：
  129
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氨基吲唑 、 对硝基苯磺酰氯 在 吡啶 作用下， 反应 2.0h， 以73%的产率得到N-(1H-indazol-5-yl)-4-nitro-benzenesulfonamide
  参考文献：
  名称：

  N-（2-甲基-吲哚-1H-5-基）-1-萘磺酰胺：一种新型可逆的抗有丝分裂剂，可抑制癌细胞的运动

  摘要：

  合成了一系列含有磺酰胺骨架的化合物，并筛选了它们对人癌细胞系代表细胞的体外抗癌活性，从而鉴定出N-（2-甲基-1H-吲哚-5-基）-1 -萘磺酸酰胺（8e）作为化合物在整个面板上均显示出显着的活性，IC50值在纳摩尔至低微摩尔范围内。细胞周期分布分析显示8e促进了严重的G2 / M阻滞，随后在8e处理的细胞中检测到与衰老相关的β-半乳糖苷酶（SA-β-gal），表明细胞发生了衰老。延长的8e治疗还导致凋亡的发生，与Caspase 3/7活性增加的检测有关。尽管γ-H2A.X水平升高，但DNA双链断裂的公认读数，用8e进行的体外DNA结合研究不支持与DNA的相互作用。与此相符，8e无法激活细胞DNA损伤检查点。重要的是，微管蛋白染色显示8e促进了微管的严重混乱，并且在8e处理的细胞中未检测到有丝分裂纺锤体的形成。因此，8e在体外以剂量依赖的方式抑制微管蛋白的聚合，并且还能够强有力地抑制癌细胞

  DOI：

  10.1016/j.bcp.2016.06.016

文献信息

• In vivo and in vitro anti-leishmanial activities of 4-nitro-N-pyrimidin- and N-pyrazin-2-ylbenzenesulfonamides, and N2-(4-nitrophenyl)-N1-propylglycinamide
  作者：M. Auxiliadora Dea-Ayuela、Encarna Castillo、Marta Gonzalez-Alvarez、Celeste Vega、Miriam Rolón、Francisco Bolás-Fernández、Joaquín Borrás、M. Eugenia González-Rosende

  DOI：10.1016/j.bmc.2009.09.030

  日期：2009.11

  A series of compounds containing the nitrobenzene and sulfonamido moieties were synthesized and their leishmanicidal effect was assessed in vitro against Leishmania infantum promastigotes. Among the compounds evaluated, the p-nitrobenzenesulfonamides 4Aa and 4Ba, and the p-nitroaniline 5 showed significant activity with a good selectivity index. In a Balb/c mice model of L. Infantum, administration of compounds 4Aa, 4Ba or 5 (5 mg/kg/day for 10 days, injected ip route) led to a clear-cut parasite burden reduction (ca. 99%). In an attempt to elucidate their mechanism of action, the DNA interaction of 4Aa and 5 was investigated by means of viscosity studies, thermal denaturation and nuclease activity assay. Both compounds showed nuclease activity in the presence of copper salt. The results suggest that compounds 4Aa, 4Ba and 5 represent possible candidates for drug development in the therapeutic control of leishmaniasis. (C) 2009 Elsevier Ltd. All rights reserved.
• In Vitro and in Vivo Antileishmanial and Trypanocidal Studies of New <i>N</i>-Benzene- and <i>N</i>-Naphthalenesulfonamide Derivatives
  作者：Cristina Galiana-Roselló、Pablo Bilbao-Ramos、M. Auxiliadora Dea-Ayuela、Miriam Rolón、Celeste Vega、Francisco Bolás-Fernández、Enrique García-España、Jorge Alfonso、Cathia Coronel、M. Eugenia González-Rosende

  DOI：10.1021/jm4006127

  日期：2013.11.27

  We report in vivo and in vitro antileishmanial and trypanocidal activities of a new series of N-substituted benzene and naphthalenesulfonamides 1-15. Compounds 1-15 were screened in vitro against Leishmania infantum, Leishmania braziliensis, Leishmania guyanensis, Leishmania amazonensis, and Trypanosoma cruzi. Sulfonamides 6e, 10b, and 10d displayed remarkable activity and selectivity toward T. cruzi epimastigotes and amastigotes. 6e showed significant trypanocidal activity on parasitemia in a murine model of acute Chagas disease. Moreover, 6e, 8c, 9c, 12c, and 14d displayed interesting IC50 values against Leishmania spp promastigotes as well as L. amazonensis and L. infantum amastigotes. 9c showed excellent in vivo activity (up to 97% inhibition of the parasite growth) in a short-term treatment murine model for acute infection by L. infantum. In addition, the effect of compounds 9c and 14d on tubulin as potential target was assessed by confocal microscopy analysis applied to L. infantum promastigotes.
• N-(2-methyl-indol-1H-5-yl)-1-naphthalenesulfonamide: A novel reversible antimitotic agent inhibiting cancer cell motility
  作者：Clara Aceves-Luquero、Cristina Galiana-Roselló、Guillem Ramis、Ruth Villalonga-Planells、Enrique García-España、Silvia Fernández de Mattos、Rafael Peláez、José M. Llinares、M. Eugenia González-Rosende、Priam Villalonga

  DOI：10.1016/j.bcp.2016.06.016

  日期：2016.9

  8e-treated cells. Accordingly, 8e inhibited tubulin polymerization in vitro in a dose-dependent manner and was also able to robustly inhibit cancer cell motility. Docking analysis revealed a compatible interaction with the colchicine-binding site of tubulin. Remarkably, these cellular effects were reversible since disruption of treatment resulted in the reorganization of microtubules, cell cycle re-entry

  合成了一系列含有磺酰胺骨架的化合物，并筛选了它们对人癌细胞系代表细胞的体外抗癌活性，从而鉴定出N-（2-甲基-1H-吲哚-5-基）-1 -萘磺酸酰胺（8e）作为化合物在整个面板上均显示出显着的活性，IC50值在纳摩尔至低微摩尔范围内。细胞周期分布分析显示8e促进了严重的G2 / M阻滞，随后在8e处理的细胞中检测到与衰老相关的β-半乳糖苷酶（SA-β-gal），表明细胞发生了衰老。延长的8e治疗还导致凋亡的发生，与Caspase 3/7活性增加的检测有关。尽管γ-H2A.X水平升高，但DNA双链断裂的公认读数，用8e进行的体外DNA结合研究不支持与DNA的相互作用。与此相符，8e无法激活细胞DNA损伤检查点。重要的是，微管蛋白染色显示8e促进了微管的严重混乱，并且在8e处理的细胞中未检测到有丝分裂纺锤体的形成。因此，8e在体外以剂量依赖的方式抑制微管蛋白的聚合，并且还能够强有力地抑制癌细胞