Study on Synthesis and Biological Activities of New Aromatic Acylhydrazone Compounds

doi:10.14088/j.cnki.issn0439-8114.2018.14.015

Abstract

Abstract: Taking p-chlorobenzoic acid, methanol, hydrazine hydrate and chlorinated benzaldehyde as materials, three new aromatic acylhydrazone schiff base compounds, namely o-chlorobenzaldehyde p-chlorobenzoyl hydrazone, p-chlorobenzaldehyde p-chlorobenzoyl hydrazone and 2, 4-chlorobenzaldehyde p-chlorobenzoyl hydrazone were designed and synthesized. The structures of target molecules were confirmed by elemental analysis, H¹ NMR and the infrared spectrum. Taking 5 instar larvae of Pieris rapae as test insects, the insecticidal activities of target compounds were tested in lab. The results showed that three aromatic acylhydrazone schiff base compounds had insecticidal activities against 5 instar larvae of P. rapae. Among three target compounds, 2, 4-chlorobenzaldehyde p-chlorobenzoyl hydrazone showed the strongest contact toxicity and stomach toxicity.

Key words: acylhydrazone, schiff base, synthesis, biological activities

CLC Number:

TQ453
O621.2

XU Jing-yi, PENG Wen-qing, LIU Xu-qiang, WU Juan, HE Jia-jia, LI Shui-qing. Study on Synthesis and Biological Activities of New Aromatic Acylhydrazone Compounds[J]. HUBEI AGRICULTURAL SCIENCES, 2018, 57(14): 64-66.

References

[1] GÖKOLU E, YıLMAZ E, GÖKOLU E, et al. Study of binding properties between two new ibuprofen and naproxen based acyl hydrazone derivatives and trypsin[J].Journal of Fluorescence, 2016, 26:113-119.
[2] 解庆范, 林长新, 刘春霞, 等.4-(二乙氨基)水杨醛席夫碱的合成、光谱性质和热稳定性及量化计算[J].化学研究, 2016, 27(1):88-91.
[3] INAM A, SIDDIQUI S M, MACEDO T S, et al.Design, synthesis and biological evaluation of 3-[4-(7-chloro-quinolin-4-yl)-piperazin-1-yl]-propionic acid hydrazones as antiprotozoal agents[J].European Journal of Medicinal Chemistry, 2014, 75(21):67-76.
[4] SERAFIM R A M, GONCALVES J E, FELIPE P S, et al. Design, synthesis and biological evaluation of hybrid bioisoster derivatives of N-acylhydrazone and furoxan groups with potential and selective anti-Trypanosoma cruzi activity[J].European Journal of Medicinal Chemistry, 2014, 82:418-425.
[5] MU J X, SHI Y X, WU H K, et al.Microwave assisted synthesis, antifungal activity, DFT and SAR study of 1, 2, 4-triazolo[4, 3-a]pyridine derivatives containing hydrazone moieties[J].Chemistry Central Journal, 2016, 10:50-58.
[6] JOSHI S D, KUMAR D, DIXIT S R, et al.Synthesis, characterization and antitubercular activities of novel pyrrolyl hydrazones and their Cu-complexes[J].European Journal of Medicinal Chemistry, 2016, 121:21-39.
[7] 冯洋, 李传碧, 赵丽婷, 等.新型含巴比妥酸的芳香酰腙类化合物的合成、晶体结构及抑菌活性[J].应用化学, 2016, 33(8):913-922.
[8] TURAN-ZITOUNI G, YURTTAS L, KAPLANCıKLı Z A, et al. Synthesis and anti-nociceptive, anti-inflammatory activities of new aroyl propionic acid derivatives including N-acylhydrazone motif[J].Medicinal Chemistry Research, 2015, 24:2406-2416.
[9] ZHANG F, WANG X L, SHI J, et al.Synthesis, molecular modeling and biological evaluation of N-benzylidene-2-((5-(pyridin-4-yl)-1, 3, 4-oxadiazol-2-yl)thio)acetohydrazide derivatives as potential anticancer agents[J].Bioorganic & Medicinal Chemistry, 2014, 22(1):468-477.
[10] 魏敦灿, 王红, 张鲁勉, 等.取代呋喃醛缩苯磺酰腙化合物的合成及抗肿瘤活性研究[J].汕头大学医学院学报, 2016, 29(1):1-2.
[11] 冯泳兰, 方敬贤, 刘超, 等.3, 5-二氯水杨醛缩罗丹明B酰腙的合成及对Cu²+高选择性识别[J].无机化学学报, 2016, 32(1):56-62.
[12] 于明坤, 刘向荣, 闫森, 等.含卤素原子酰腙化合物的合成、表征及与ct-DNA的相互作用[J].化学通报, 2016, 79(7):616-622.
[13] 张文吉, 李学锋, 王成菊.农药加工及使用技术[M].北京:中国农业大学出版社, 1998.
[14] 慕立义. 植物化学保护研究方法[M].北京:中国农业出版社, 1994.
[15] 吴文君. 植物化学保护实验技术导论[M].西安:陕西科学技术出版社, 1988.