5-amino-N1-(naphthalen-3-ylsulfonyl)-1,2,4-triazole | 1444154-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-amino-N1-(naphthalen-3-ylsulfonyl)-1,2,4-triazole
• 英文别名: anstrz
• CAS: 1444154-80-6
• 化学式: C₁₂H₁₀N₄O₂S
• 分子量: 274.303
• InChiKey: TVURVQLGQKPINA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.87
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-amino-N1-(naphthalen-3-ylsulfonyl)-1,2,4-triazole 、 copper(II) acetate monohydrate 在 氨 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 0.5h， 以60%的产率得到[Cu(3,5-diamino-N1-(naphthalen-3-ylsulfonyl)-1,2,4-triazole)(μ-acetate)₂]₂
  参考文献：
  名称：

  Two copper complexes from two novel naphthalene-sulfonyl-triazole ligands: Different nuclearity and different DNA binding and cleavage capabilities

  摘要：

  Two novel naphthalene-sulfonyl-triazole ligands, 5-amino-N1-(naphthalen-3-ylsulfony1)-1,2,4-triazole (anstrz) and 3,5-diamino-N1-(naphthalen-3-ylsulfony1)-1,2,4-triazole (danstrz), purposely designed to interact with DNA, have been prepared for the first time and then fully characterized by H-1, C-13 NMR and IR spectroscopy, mass spectrometry and elemental analysis. The crystal structures of two copper complexes of these derivatives, i.e. [Cu(anstrz)(4)(NO3)(2)]center dot 4CH(3)OH (1), mononuclear, and [Cu(danstrz)(mu-OAc)(2)](2)center dot 2(danstrz) (OAc = acetato) (2), dinuclear, have been determined by single-crystal X-ray diffraction. In both cases the ligand coordinates in a monodentate fashion via the N4 nitrogen atom of the triazole ring. Compound 2, an example of paddle wheel type copper acetate, presents a Cu - Cu' distance of 2.667(1) angstrom. As a result of strong stacking interactions and intense H-bonds, the structure of 2 constitutes a MOF (metal-organic framework). Besides, this dinuclear compound exhibits a very strong antiferromagnetic coupling (J = -324 cm(-1)) and a silent X-band EPR at room temperature. The affinity toward DNA of 1 and 2 has been examined by fluorescence emission spectroscopy, thermal denaturation and viscosimetry assays. The apparent binding constant (K-app) values of 2.2 x 10(7) M-1 for 1 and 2.6 x 10(7) M-1 for 2 suggest important DNA interaction. The dinuclear compound (2) intercalates and produces a high change in the T-m. Both compounds promote DNA scission in the presence of H2O2/ascorbate (1) or ascorbate (2) through oxidative mechanism. The possible reasons for the higher DNA affinity and the more efficient DNA cleavage displayed by compound 2 in relation to compound 1 are discussed. (c) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2013.04.007
• 作为产物：
  描述：

  2-萘磺酰氯 、 3-氨基-1,2,4-三氮唑 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以86%的产率得到5-amino-N1-(naphthalen-3-ylsulfonyl)-1,2,4-triazole
  参考文献：
  名称：

  Two copper complexes from two novel naphthalene-sulfonyl-triazole ligands: Different nuclearity and different DNA binding and cleavage capabilities

  摘要：

  Two novel naphthalene-sulfonyl-triazole ligands, 5-amino-N1-(naphthalen-3-ylsulfony1)-1,2,4-triazole (anstrz) and 3,5-diamino-N1-(naphthalen-3-ylsulfony1)-1,2,4-triazole (danstrz), purposely designed to interact with DNA, have been prepared for the first time and then fully characterized by H-1, C-13 NMR and IR spectroscopy, mass spectrometry and elemental analysis. The crystal structures of two copper complexes of these derivatives, i.e. [Cu(anstrz)(4)(NO3)(2)]center dot 4CH(3)OH (1), mononuclear, and [Cu(danstrz)(mu-OAc)(2)](2)center dot 2(danstrz) (OAc = acetato) (2), dinuclear, have been determined by single-crystal X-ray diffraction. In both cases the ligand coordinates in a monodentate fashion via the N4 nitrogen atom of the triazole ring. Compound 2, an example of paddle wheel type copper acetate, presents a Cu - Cu' distance of 2.667(1) angstrom. As a result of strong stacking interactions and intense H-bonds, the structure of 2 constitutes a MOF (metal-organic framework). Besides, this dinuclear compound exhibits a very strong antiferromagnetic coupling (J = -324 cm(-1)) and a silent X-band EPR at room temperature. The affinity toward DNA of 1 and 2 has been examined by fluorescence emission spectroscopy, thermal denaturation and viscosimetry assays. The apparent binding constant (K-app) values of 2.2 x 10(7) M-1 for 1 and 2.6 x 10(7) M-1 for 2 suggest important DNA interaction. The dinuclear compound (2) intercalates and produces a high change in the T-m. Both compounds promote DNA scission in the presence of H2O2/ascorbate (1) or ascorbate (2) through oxidative mechanism. The possible reasons for the higher DNA affinity and the more efficient DNA cleavage displayed by compound 2 in relation to compound 1 are discussed. (c) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2013.04.007