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Citation: ZHANG Jin-Yan, XIAO Xiao-Ming, TAN Nian-Yuan, XU Sha-Sha, OUYANG Ze-Ying. Synthesis of 2,6-Di(2'-imidazoline-2'-yl)Pyridine under Microwave Irradiation and Interaction with DNA[J]. Chinese Journal of Applied Chemistry, ;2010, 27(6): 658-663. doi: 10.3724/SP.J.1095.2010.90532 shu

Synthesis of 2,6-Di(2'-imidazoline-2'-yl)Pyridine under Microwave Irradiation and Interaction with DNA

a. College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081;
b. College of Chemistry and Chemical Engineering, Hunan Institute of Engineering, Xiangtan

Received Date: 13 August 2009
Revised Date: 27 October 2009

2,6-Di(2'-imidazoline-2'-yl)pyridine,even though it is not fully aromatic,has the same distribution of heteroatoms as 2,6-di(2'-benzimidazol-2'-yl)pyridine and has been synthesized from pyridine 2,6-dicarboxylic acid and ethylenediamine under microwave irradiation and without catalyst. The composition and structure of the product were identified and characterized by IR,mass spectrometry,¹H NMR,¹³C NMR and melting point determination. The ratio of products and by-product was found to be different under different experimental conditions(solvents,proportion of reacting mass,power of microwave irradiation). Among them,solvents have very obvious effects on the ratio of product and by-product. The experimental results indicate that the best solvent is ethylene glycol. The optimal reaction condition are follows:molar ratio of raw materials 1:2.7,microwave power 450 W,irradiation time 65 min,irradiation temperature 130℃ and the overall yield 71.2%.The binding of this compound with calf thymus DNA was investigated by UV and viscosity measurements.The binding constant K_b is meaused to be(9.60±0.05)×10⁴ L/mol,which is lower than those observed for typical classical intercalators.The results of viscosity measurement reveal that the presence of 2,6-di(2'-imidazoline-2'-yl)pyridine has no obvious effect on the relative viscosity of DNA.It may bind to DNA by hydrogen bonding and groove-face binding.
- di(imidazolineyl)pyridine,
- ethylenediamine,
- microwave irradiation,
- synthesis,
- DNA
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