4-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide | 1456736-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide
• 英文别名: 4-[4-(naphthalen-1-yloxymethyl)triazol-1-yl]-N-(2-phenylethyl)benzenesulfonamide
• CAS: 1456736-79-0
• 化学式: C₂₇H₂₄N₄O₃S
• 分子量: 484.579
• InChiKey: JWDAIZNHIQKFOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-氨基-N-(2-苯基乙基)苯磺酰胺 在 盐酸 、 Vitamin C 、 copper(II) sulfate pentahydrate 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.75h， 生成 4-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamides

  摘要：

  A new series of 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide derivatives 5 were synthesized through the Click approach and evaluated for their cytotoxic activity against four cancer cell lines (HuCCA-1, HepG2, A549, and MOLT-3). Most of the synthesized triazoles 5 displayed cytotoxicity against MOLT-3 cell line, except for analogs 5a-c and 5e. Significantly, 4-phenyltriazoles (5a and 5n), 4-(naphthalen-2-yloxy)methyltriazole 5d, as well as 4-((2-oxo-2H-chromen-7-yl)oxy)methyltriazole 5l showed higher cytotoxic activity against HepG2 cells than the reference drug, etoposide. Interestingly, the 4-phenyltriazole 5a was the most potent and promising compound with IC50 value of 9.07 mu M against HepG2 cell line. The analog 5a also exerted the highest cytotoxic activity against HuCCA-1 cells. This finding provides the novel lead molecules for further development.

  DOI：

  10.1007/s00044-013-0777-z

文献信息

• Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamides
  作者：Ratchanok Pingaew、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1007/s00044-013-0777-z

  日期：2014.4

  A new series of 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide derivatives 5 were synthesized through the Click approach and evaluated for their cytotoxic activity against four cancer cell lines (HuCCA-1, HepG2, A549, and MOLT-3). Most of the synthesized triazoles 5 displayed cytotoxicity against MOLT-3 cell line, except for analogs 5a-c and 5e. Significantly, 4-phenyltriazoles (5a and 5n), 4-(naphthalen-2-yloxy)methyltriazole 5d, as well as 4-((2-oxo-2H-chromen-7-yl)oxy)methyltriazole 5l showed higher cytotoxic activity against HepG2 cells than the reference drug, etoposide. Interestingly, the 4-phenyltriazole 5a was the most potent and promising compound with IC50 value of 9.07 mu M against HepG2 cell line. The analog 5a also exerted the highest cytotoxic activity against HuCCA-1 cells. This finding provides the novel lead molecules for further development.
• Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors
  作者：Ratchanok Pingaew、Veda Prachayasittikul、Prasit Mandi、Chanin Nantasenamat、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1016/j.bmc.2015.04.036

  日期：2015.7

  A series of 1,4-disubstituted-1,2,3-triazoles (13-35) containing sulfonamide moiety were synthesized and evaluated for their aromatase inhibitory effects. Most triazoles with open-chain sulfonamide showed significant aromatase inhibitory activity (IC50 = 1.3-9.4 mu M). Interestingly, the meta analog of triazole-benzene-sulfonamide (34) bearing 6,7-dimethoxy substituents on the isoquinoline ring displayed the most potent aromatase inhibitory activity (IC50 = 0.2 mu M) without affecting normal cell. Molecular docking of these triazoles against aromatase revealed that the compounds could snugly occupy the active site of the enzyme through hydrophobic, pi-pi stacking, and hydrogen bonding interactions. The potent compound 34 was able to form hydrogen bonds with Met374 and Ser478 which were suggested to be the essential residues for the promising inhibition. The study provides compound 34 as a potential lead molecule of anti-aromatase agent for further development. (C) 2015 Elsevier Ltd. All rights reserved.