4-nitro-N-4-methyl-thiazol-2-yl-benzenesulfonamide | 103273-92-3

• 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-nitro-N-4-methyl-thiazol-2-yl-benzenesulfonamide
• 英文别名: 4-nitro-benzenesulfonic acid-(4-methyl-thiazol-2-ylamide)；4-Nitro-benzolsulfonsaeure-(4-methyl-thiazol-2-ylamid)；N-(4-methyl-1,3-thiazol-2-yl)-4-nitrobenzenesulfonamide
• CAS: 103273-92-3
• 化学式: C₁₀H₉N₃O₄S₂
• 分子量: 299.331
• InChiKey: AFYZOKKPCCRBSL-UHFFFAOYSA-N

物化性质

• 熔点：
  197-199 °C
• 沸点：
  503.4±52.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-nitro-N-4-methyl-thiazol-2-yl-benzenesulfonamide 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 20.0~50.0 ℃ 、5.0 MPa 条件下， 反应 18.0h， 生成 4-(2-hydroxy-3-methoxybenzylamino)-N-(4-methylthiazol-2-yl)benzenesulfonamide
  参考文献：
  名称：

  4-（（2-羟基-3-甲氧基苄基）氨基）苯磺酰胺衍生物作为 12-脂氧化酶的强效和选择性抑制剂的合成和构效关系研究

  摘要：

  人类脂肪氧化酶 (LOX) 是一类含铁酶，可催化多不饱和脂肪酸氧化以提供相应的生物活性羟基二十碳四烯酸 (HETE) 代谢物。这些类二十烷酸信号分子参与了许多生理反应，例如血小板聚集、炎症和细胞增殖。我们小组对血小板型 12-( S )-LOX (12-LOX)产生了特别的兴趣，因为它在皮肤病、糖尿病、血小板止血、血栓形成和癌症中发挥了重要作用。在此，我们报告了基于 4-（（2-羟基-3-甲氧基苄基）氨基）苯磺酰胺的支架的鉴定和药物化学优化。顶级化合物，以35和36为例, 显示对 12-LOX 的 nM 效力，对相关脂肪氧化酶和环氧化酶具有出色的选择性，并具有良好的 ADME 特性。此外，这两种化合物均抑制 PAR-4 诱导的人血小板聚集和钙动员，并减少 β 细胞中的 12-HETE。

  DOI：

  10.1021/jm4016476
• 作为产物：
  描述：

  4-nitro-benzenesulfenic acid-(4-methyl-thiazol-2-ylamide) 在 potassium permanganate 、 溶剂黄146 作用下， 生成 4-nitro-N-4-methyl-thiazol-2-yl-benzenesulfonamide
  参考文献：
  名称：

  DE902010

  摘要：

  公开号：

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.
• DE902010
  申请人：——

  公开号：——

  公开（公告）日：——
• Sulfanilamido Derivatives of Heterocyclic Amines
  作者：Russel J. Fosbinder、L. A. Walter

  DOI：10.1021/ja01877a024

  日期：1939.8
• Process for preparation of sulphonamide derivatives
  申请人：ZOLTEN FOLDI

  公开号：US02332906A1

  公开（公告）日：1943-10-26