Citation: MAO Xinjie, LIU Xiangrong, ZHAO Shunsheng, YANG Zaiwen, YAN Sen. Synthesis, Crystal Structures and Calf Thymus DNA Binding of Acylhydrazone Bearing Pyrrole Ring[J]. Chinese Journal of Applied Chemistry, ;2016, 33(8): 923-931. doi: 10.11944/j.issn.1000-0518.2016.08.150398 shu

Synthesis, Crystal Structures and Calf Thymus DNA Binding of Acylhydrazone Bearing Pyrrole Ring

1.
College of Chemistry and Chemical Engineering, Xi'an University of Science and Technology, Xi'an 710054, China

Corresponding author: LIU Xiangrong,
Received Date: 13 November 2015
Available Online: 24 February 2016
Fund Project:

Two hydrazone componds(E)-N'-(2,4-dihydroxybenzylidene)-pyrrole-2-carbohydrazide C₁₂H₁₁N₃O₃(Ⅰ) and (E)-N'-(2-hydroxy-3-methoxybenzylidene)-pyrrole-2-carbohydrazide C₁₃H₁₄N₃O₄(Ⅱ) have been synthesized from 2,4-dihydroxybenzaldehyde and 2-hydroxy-3-methoxybenzaldehyde with pyrrole-2-carbohydrazide, respectively. The compounds have been characterized by IR spectroscopy, elemental analysis, ¹H NMR spectroscopy, single-crystal X-ray diffraction and thermogravimetric analysis. The crystal of compound Ⅰ belonged to monoclinic crystal lattice, space group P2₁/c, Z=4, with unit cell parameters a=1.2586(4) nm, b=0.8050(3) nm, c=1.1914(4) nm, and compound Ⅱ crystallized in the orthorhombic system, space group P2₁2₁2₁, Z=4, with unit cell parameters a=0.4756(2) nm, b=1.2491(6) nm, c=2.2145(11) nm. The TG-DTG result shows that the compounds Ⅰ and Ⅱ display good thermal stability, the maximum decomposition peaks are at the temperature of 267.59 ℃ and 284.79 ℃, and their apparent activation energy values are 176.6 kJ/mol and 122.9 kJ/mol, respectively. The thermogenic curves of the compounds Ⅰ and Ⅱ reacting with calf thymus DNA(CT-DNA) measured by viscosity and microcalorimetry, indicate that the interactions of compounds Ⅰ and Ⅱ with CT-DNA belong to the intercalation mode, and the interacting processes are all endothermic, their enthalpies are ΔH(Ⅰ)=4.67 kJ/mol and ΔH(Ⅱ)=4.40 kJ/mol, respectively.
- hydrazone,
- crystal structures,
- thermal stability,
- calf thymus DNA
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沈阳化工大学材料科学与工程学院沈阳 110142