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以2-吡咯甲酰肼与2,4-二羟基苯甲醛和2-羟基-3-甲氧基苯甲醛经缩合反应合成2,4-二羟基苯甲醛-2-吡咯甲酰腙C12H11N3O3(Ⅰ)和2-羟基-3-甲氧基苯甲醛-2-吡咯甲酰腙C13H15N3O4(Ⅱ),并利用红外光谱、元素分析、1H NMR、X射线单晶衍射和热重分析进行表征,结果表明晶体Ⅰ属单斜晶系,空间群为P21/c,Z=4,晶胞参数为a=1.2586(4)nm,b=0.8050(3)nm,c=1.1914(4)nm;晶体Ⅱ为正交晶系,空间群为P212121Z=4,晶胞参数为a=0.4756(2)nm,b=1.2491(6)nm,c=2.2145(11)nm。热重结果显示,化合物Ⅰ和Ⅱ最大热分解峰分别出现在267.59和284.79 ℃,表观活化能分别为176.6和122.9 kJ/mol,表明化合物Ⅰ和Ⅱ具有较高的热稳定性。利用粘度实验和微量热实验研究了化合物Ⅰ和Ⅱ与CT-DNA的相互作用,均显示两种化合物均与CT-DNA发生了插入作用,且相互作用过程放热,焓变值分别为ΔH(Ⅰ)=4.67 kJ/mol和ΔH(Ⅱ)=4.40 kJ/mol。

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.

参考文献

[1] Singh R N,Kumar A,Tiwari R K,et al. Synthesis, Multiple Interactions and Spectroscopy Analysis of Ethyl-4-[(benzoyl)-hydrazonomethyl]-3,5-dimethyl-1H-pyrrole-2-carboxylate:Through Experimental and Quantum Chemical Approaches[J]. J Mol Struct,2013,1035(5):295-306.
[2] Guessan N,Boko P,Akogbebo A,et al. Chlorfenapyr:A Pyrrole Insecticide for the Control of Pyrethroid or DDT Resistant Anopheles Gambiae(Diptera:Culicidea) Mosquitos[J]. Acta Trop,2007,102(1):69-78.
[3] Narule M N,Gaidhane M K,Gaidhane P K. Synthesis, Characterization, Biologically and Antioxidant Active of Some 2-Substitued 3,5-Dimethyl-4-ethoxy carbonyl Pyrrole Derivatives[J]. J Pharm Res,2013,6(6):626-632.
[4] Bandyopadhyay D,Mukherjee S,Granados J C,et al. Ultrasound-assisted Bismuth Nitrate-induced Green Synthesis of Novel Pyrrole Derivatives and Their Biological Evaluation as Anticancer Agents[J]. Eur J Med Chem,2012,50:209-215.
[5] LI Yanzhong,ZHAO Ping,ZHAN Xiaoping,et al. Synthesis and Cytotoxic Activities of Novel Amino Acid-Conjugates of Pyrrole Derivatives[J]. Chinese J Org Chem,2015,35(1):167-174(in Chinese).
李衍忠,赵萍,詹小平,等. 新型吡咯类氨基酸缀合物的合成与抗肿瘤活性测定[J]. 有机化学,2015,35(1):167-174.
[6] LIU Dongmei,ZHENG Songzhi,An Shengji,et al. Structure, Synthesis and Application of Calixpyrrole and Hetero-calixpyrrole[J]. Chinese J Org Chem,2008,28(3):398-406(in Chinese).
刘冬美,郑松志,安胜姬,等. 杯吡咯和杂环吡咯的结构、合成及应用[J]. 有机化学,2008,28(3):398-406.
[7] Asati V,Sahu N K,Rathore A,et al. Synthesis, Characterization and Antimicrobial Evaluation of Some 1,3-Benzothiazole-2-yl-hydrazone Derivatives[J]. Arab J Chem,2015,8(4):495-499.
[8] Cui J G,Liu L,Zhao D D,et al. Synthesis, Characterization and Antitumor Activities of Some Sterodial Derivatives with Side Chain of 17-Hydrazone Aromatic Heterocycle[J]. Steroids,2015,95:32-38.
[9] LU Jiufu,BAI Yuefei,ZHOU Peng. Synthesis and Antituberculous Activities of Novel Aromatic Aldehyde Benzoyl Hydrazone Derivatives[J]. Chinese J Synth Chem,2015,23(1):31-35(in Chinese).
卢久福,白跃飞,周鹏. 新型芳醛并苯甲酰腙类化合物的合成及其抗结核活性[J]. 合成化学,2015,23(1):31-35.
[10] Ren J W,Liu X R,Yang Z W,et al. Thermal Properties and DNA-binding Studies of a New Kind of Acyl Hydrazone Compounds Containing Imidazole Ring[J]. Thermochim Acta,2014,582(4):17-24.
[11] ZHENG Changzheng,DU Xiaodi,QUAN Li,et al. Synthesis, Crystal Structure and Antibacterial Activities of Cu(Ⅱ) Complex with 2-Furaldehyde Salicylhydrazone Hydrazone[J]. J Synth Cryst,2014,43(9):2434-2438(in Chinese).
郑长征,杜筱迪,权俐,等. 2-呋喃甲醛水杨酰腙铜配合物的合成、晶体结构及抑菌活性[J]. 人工晶体学报,2014,43(9):2434-2438.
[12] Ye X P,Wang G J,Pan P,et al. Syntheses, Crystal Structures and Biological Activities of Two Cu(Ⅱ) Complexes with an Acylhydrazone Ligand Bearing Pyrrole Unit[J]. Chinese J Org Chem,2014,30(12):2789-2795.
[13] Wang L N,Liu X R,Yang C,et al. 1-H-Pyrrole-2-carbohydrazide[J]. Acta Crystallogr,Sect E,2011,E67:493.
[14] Sheldrick G M. A Short History of SHELX[J]. Acta Cryst,2008,A64(1):112-122.
[15] Satyanarayana S,Daborwiak J C,Chairs J B. Tris(phenanthroline) Ruthenium(Ⅱ) Enantiomer Interactions with DNA:Mode and Specificity of Binding[J]. Biochemistry,1993,32(10):2573-2584.
[16] Bei F L,Jian F F,Yang X J,et al. 1,4-Bis(2-benzimidazolyl)benzene[J]. Acta Crystallogr,Sect C,2000,56(6):718-719.
[17] HU Rongzu,GAO Shengli,ZHAO Fengqi,et al. Thermal Analysis Kinetics[M]. Second Edition.Beijing:China Science Press,2008:54-131(in Chinese).
胡荣祖,高胜利,赵凤起,等. 热分析动力学[M]. 第2版. 北京:科学出版社,2008:54-131.
[18] ZHENG Jianhua,LIU Jun,XIAO Yao,et al. Synthesis, Crystal Structure, Thermal Stability and DNA Interaction of the Dibutytin Complex Based on Salicylacylhydrazone[J]. Chinese J Appl Chem,2015,32(5):362-369(in Chinese).
郑建华,刘俊,肖尧,等. 基于水杨酰腙配体的二丁基锡配合物的合成、晶体结构、热稳定性及与DNA相互作用[J]. 应用化学,2015,32(5):362-369.
[19] ZHANG Lin,SHAO Shengyu,WEN Hongyu. Microcalorimetric Study on the Reaction between Flavonoids and DNA[J]. Life Sci Instrum,2008,6(2):28-31(in Chinese).
张琳,邵晟宇,温红宇. 黄酮类化合物与DNA作用的热力学研究[J]. 生命科学仪器,2008,6(2): 28-31.
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