N′-((2-hydroxynaphthalen-1-yl)methylene)-5-methyl-1H-pyrazole-3-carbohydrazide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N′-((2-hydroxynaphthalen-1-yl)methylene)-5-methyl-1H-pyrazole-3-carbohydrazide
• 英文别名: N-[(2-hydroxynaphthalen-1-yl)methylideneamino]-5-methyl-1H-pyrazole-3-carboxamide
• 化学式: C₁₆H₁₄N₄O₂
• mdl: MFCD00408140
• 分子量: 294.313
• InChiKey: ZOQULRMFSBBJJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N′-((2-hydroxynaphthalen-1-yl)methylene)-5-methyl-1H-pyrazole-3-carbohydrazide 、 水 、 zinc(II) chloride 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以55%的产率得到
  参考文献：
  名称：

  Photophysical properties and biological evaluation of a Zinc(II)-5-methyl-1H-pyrazole Schiff base complex

  摘要：

  A new ZnL2 complex containing two molecules of a tridentate Schiff base derived from 5-methyl-1H-pyrazole (HL) is synthesized and characterized. The photophysical properties of HL and ZnL2 are disclosed and supported by CAMB3LYP DFT/TDDFT calculations. It is shown that there is keto-tautomer stabilization upon excitation with an energetically accessible triplet state in HL, not present in ZnL2, this explaining the differences found in the emissions of the compounds. The intrinsic fluorescence of ZnL2 is used as probe for a detailed study of its binding to human serum albumin. The protein-complex association is thermodynamically favourable and it is shown by fluorescence quenching and time-resolved analysis that the fluorescence quenching involves a mixed mechanism with prevalence of static quenching, which corroborates adduct formation at site I, close to the Trp214 residue. The ability of ZnL2 to bind DNA was also evaluated, as well as its cytotoxic activity against MCF7 (breast), PC3 (prostate) cancer cells and hamster V79 fibroblasts. ZnL2 is a moderate DNA intercalator (K-app = 3.9 x 10(4) M-1) and depicts a quite low IC50 value at 48 h against MCF7 cells (IC50 = 530 nM), but much higher for PC3 and V79 cells. The relevance of a more careful speciation evaluation of ZnL2 and other potential metal based drugs in incubation media used in in vitro tests is highlighted. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2018.06.028
• 作为产物：
  描述：

  1H-吡唑-5-碳酰肼 、 2-羟基-1-萘甲醛 在 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 N′-((2-hydroxynaphthalen-1-yl)methylene)-5-methyl-1H-pyrazole-3-carbohydrazide
  参考文献：
  名称：

  Photophysical properties and biological evaluation of a Zinc(II)-5-methyl-1H-pyrazole Schiff base complex

  摘要：

  A new ZnL2 complex containing two molecules of a tridentate Schiff base derived from 5-methyl-1H-pyrazole (HL) is synthesized and characterized. The photophysical properties of HL and ZnL2 are disclosed and supported by CAMB3LYP DFT/TDDFT calculations. It is shown that there is keto-tautomer stabilization upon excitation with an energetically accessible triplet state in HL, not present in ZnL2, this explaining the differences found in the emissions of the compounds. The intrinsic fluorescence of ZnL2 is used as probe for a detailed study of its binding to human serum albumin. The protein-complex association is thermodynamically favourable and it is shown by fluorescence quenching and time-resolved analysis that the fluorescence quenching involves a mixed mechanism with prevalence of static quenching, which corroborates adduct formation at site I, close to the Trp214 residue. The ability of ZnL2 to bind DNA was also evaluated, as well as its cytotoxic activity against MCF7 (breast), PC3 (prostate) cancer cells and hamster V79 fibroblasts. ZnL2 is a moderate DNA intercalator (K-app = 3.9 x 10(4) M-1) and depicts a quite low IC50 value at 48 h against MCF7 cells (IC50 = 530 nM), but much higher for PC3 and V79 cells. The relevance of a more careful speciation evaluation of ZnL2 and other potential metal based drugs in incubation media used in in vitro tests is highlighted. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2018.06.028

文献信息

• Photophysical properties and biological evaluation of a Zinc(II)-5-methyl-1H-pyrazole Schiff base complex
  作者：Nádia Ribeiro、Roberto E. Di Paolo、Adelino M. Galvão、Fernanda Marques、João Costa Pessoa、Isabel Correia

  DOI：10.1016/j.saa.2018.06.028

  日期：2018.11

  A new ZnL2 complex containing two molecules of a tridentate Schiff base derived from 5-methyl-1H-pyrazole (HL) is synthesized and characterized. The photophysical properties of HL and ZnL2 are disclosed and supported by CAMB3LYP DFT/TDDFT calculations. It is shown that there is keto-tautomer stabilization upon excitation with an energetically accessible triplet state in HL, not present in ZnL2, this explaining the differences found in the emissions of the compounds. The intrinsic fluorescence of ZnL2 is used as probe for a detailed study of its binding to human serum albumin. The protein-complex association is thermodynamically favourable and it is shown by fluorescence quenching and time-resolved analysis that the fluorescence quenching involves a mixed mechanism with prevalence of static quenching, which corroborates adduct formation at site I, close to the Trp214 residue. The ability of ZnL2 to bind DNA was also evaluated, as well as its cytotoxic activity against MCF7 (breast), PC3 (prostate) cancer cells and hamster V79 fibroblasts. ZnL2 is a moderate DNA intercalator (K-app = 3.9 x 10(4) M-1) and depicts a quite low IC50 value at 48 h against MCF7 cells (IC50 = 530 nM), but much higher for PC3 and V79 cells. The relevance of a more careful speciation evaluation of ZnL2 and other potential metal based drugs in incubation media used in in vitro tests is highlighted. (C) 2018 Elsevier B.V. All rights reserved.