3-methyl-1-(4-nitrobenzenesulfonyl)piperidine | 321970-50-7

• 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: 3-methyl-1-(4-nitrobenzenesulfonyl)piperidine
• 英文别名: 3-Methyl-1-(4-nitrophenyl)sulfonylpiperidine
• CAS: 321970-50-7
• 化学式: C₁₂H₁₆N₂O₄S
• 分子量: 284.336
• InChiKey: TVUDMFVXAQIEEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-1-(4-nitrobenzenesulfonyl)piperidine 在 铁粉 、 氯化铵 作用下， 以 水 、 甲苯 为溶剂， 生成 4-[(3-Methylpiperidin-1-yl)sulfonyl]aniline
  参考文献：
  名称：

  苯磺酰胺衍生物作为有效TRPV4抑制剂治疗急性肺损伤的探索及构效关系研究

  摘要：

  RN-9893 是 Renovis Inc. 鉴定的一种 TRPV4 拮抗剂，表现出对 TRPV4 通道的显着抑制作用。这项研究涉及合成和评估三个系列的 RN-9893 类似物的 TRPV4 抑制功效。值得注意的是，与 RN-9893 (IC = 2.07 ± 0.90 μM) 相比，化合物和对 TRPV4 的抑制效力增加了 2.9 至 4.5 倍 (IC = 0.71 ± 0.21 μM 和 0.46 ± 0.08 μM)。两种化合物的 TRPV4 当前抑制率也显着优于 RN-9893（10 μM 时为 87.6 % 和 83.2 %，而 RN-9893 为 49.4 %）。首次在小鼠模型中对这些 RN-9893 类似物进行了分析，腹腔注射 10 mg/kg 或 10 mg/kg 可显着减轻脂多糖 (LPS) 诱导的急性肺损伤症状。这些结果表明化合物和化合物是治疗急性肺损伤的有希望的候选者。

  DOI：

  10.1016/j.bioorg.2024.107396
• 作为产物：
  描述：

  对硝基苯磺酰氯 、 3-甲基哌啶 在 吡啶 作用下， 反应 2.0h， 以81%的产率得到3-methyl-1-(4-nitrobenzenesulfonyl)piperidine
  参考文献：
  名称：

  In Vitro and in Vivo Antileishmanial and Trypanocidal Studies of New N-Benzene- and N-Naphthalenesulfonamide Derivatives

  摘要：

  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.

  DOI：

  10.1021/jm4006127

文献信息

• 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.
• Exploration and structure–activity relationship research of benzenesulfonamide derivatives as potent TRPV4 inhibitors for treating acute lung injury
  作者：Mengyuan Wang、Yuehao Zhang、Xu Cai、Shangze Yang、Shiyang Sun、Sheng Zhou、Weizhen Lv、Na Du、Yan Li、Chao Ma、Kexin Ren、Mingliang Liu、Bowen Tang、Apeng Wang、Xingjuan Chen、Pengyun Li、Kai Lv、Zhibing Zheng

  DOI：10.1016/j.bioorg.2024.107396

  日期：2024.4

  RN-9893 in TRPV4 current inhibition rates (87.6 % and 83.2 % at 10 μM, against RN-9893′s 49.4 %). For the first time, these RN-9893 analogues were profiled in an mouse model, where intraperitoneal injections of or at 10 mg/kg notably mitigated symptoms of acute lung injury induced by lipopolysaccharide (LPS). These outcomes indicate that compounds and are promising candidates for acute lung injury treatment

  RN-9893 是 Renovis Inc. 鉴定的一种 TRPV4 拮抗剂，表现出对 TRPV4 通道的显着抑制作用。这项研究涉及合成和评估三个系列的 RN-9893 类似物的 TRPV4 抑制功效。值得注意的是，与 RN-9893 (IC = 2.07 ± 0.90 μM) 相比，化合物和对 TRPV4 的抑制效力增加了 2.9 至 4.5 倍 (IC = 0.71 ± 0.21 μM 和 0.46 ± 0.08 μM)。两种化合物的 TRPV4 当前抑制率也显着优于 RN-9893（10 μM 时为 87.6 % 和 83.2 %，而 RN-9893 为 49.4 %）。首次在小鼠模型中对这些 RN-9893 类似物进行了分析，腹腔注射 10 mg/kg 或 10 mg/kg 可显着减轻脂多糖 (LPS) 诱导的急性肺损伤症状。这些结果表明化合物和化合物是治疗急性肺损伤的有希望的候选者。