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Synthesis and antifungal activity of camphoric acid-based acylhydrazone compounds

  • Xian-Li Ma , Fang-Yao Li , Wen-Gui Duan EMAIL logo , Jing-Ni Liao , Zhi-duo Lin , Gui-Shan Lin , Bo Cen and Fu-Hou Lei
Published/Copyright: March 27, 2014
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Abstract

In the search of novel potent bioactive compounds, 18 novel camphoric acid-based acylhydrazone compounds 4a4r were designed and synthesized by the condensation reaction of N-amino camphorimide (3) with substituted benzaldehyde based on camphoric acid as the starting material. The target compounds were characterized by means of Fourier transform infrared (FTIR), 1H nuclear magnetic resonance (NMR), 13C NMR, electrospray ionization-mass spectrometry (ESI-MS), and elemental analysis. The preliminary bioassay showed that the following camphoric acid-based compounds exhibited excellent antifungal activity with an inhibition ratio of 95% against Physalospora piricola at the concentration of 50 μg ml-1: o-bromophenyl acylhydrazone (4f), p-bromophenyl acylhydrazone (4g), p-methoxyphenyl acylhydrazone (4m), and p-hydroxyphenyl acylhydrazone (4p).


Corresponding author: Wen-Gui Duan, School of Chemistry and Chemical Engineering, Guangxi University, No. 100, Daxue Road, Nanning 530004, P.R. China, e-mail:

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (No. 31260164), the Open Fund of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products (No. GXFC12-01), for financial support. We are also thankful to the Research Institute of Elementar Organic Chemistry, Nankai University, for the bioassay test.

References

Aggarwal, N., Kumar, R., Srivastva, C., Dureja, P., Khurana, J.M. (2010) Synthesis of nalidixic acid based hydrazones as novel pesticides. J. Agric. Food Chem. 58:3056–3061.10.1021/jf904144eSearch in Google Scholar PubMed

Avila, C.M., Lopes, A.B., Gonçalves, A.S., Silva, L.L., Romeiro, N.C., Miranda, A.L.P., Sant’Anna, C.M.R., Barreiro, E.J., Fraga, C.A.M. (2011) Structure-based design and biological profile of (E)-N-(4-nitrobenzylidene)-2-naphthohydrazide, a novel small molecule inhibitor of IκB kinase-β. Eur. J. Med. Chem. 46:1245–1253.Search in Google Scholar

Bernardino, A.M.R., Gomes, A.O., Charret, K.S., Freitas, A.C.C., Machado, G.M.C., Canto-Cavalheiro, M.M., Leon, L.L., Amaral, V.F. (2006) Synthesis and leishmanicidal activities of 1-(4-X-phenyl)-N′-[(4-Yphenyl) methylene]-1H-pyrazole-4-carbohydrazides. Eur. J. Med. Chem. 41:80–87.Search in Google Scholar

Boeckman, R.K., Miller, Y., Savage, D., Summerton, J.E. (2011) Total synthesis of a possible specific and effective acid-targeted cancer diagnostic, a camphor derived bis-N-oxide dimer. Tetrahedron Lett. 52:2243–2245.10.1016/j.tetlet.2011.01.028Search in Google Scholar

Ding, Y.G., Ma, H.M., Zhang, B.L. (2012) Research on pharmacology, toxicology and safety of camphor: review and prospect. Chin. J. Pharmacovigil. 9:38–42 (in Chinese).Search in Google Scholar

Huang, M.Z., Huang, K.L., Chen, C., Zhang, C.L., Wang, Y.J. (2004) Synthesis and bioactivity of 2-methylthio-1-phenylethanone benzoylhydrazones. Chin. J. Pestic. Sci. 6:67–70 (in Chinese).10.1002/hc.10214Search in Google Scholar

Jin, Y.X., Tan, Z.W., He, M.Z., Tian, B.H., Tang, S.X., Hewlett, I., Yang, M. (2010) SAR and molecular mechanism study of novel acylhydrazone compounds targeting HIV-1 CA. Bioorg. Med. Chem. 18:2135–2140.Search in Google Scholar

Lacerda, R.B., Lima, C.K.F., Silva, L.L., Romeiro, N.C., Miranda, A.L.P., Barreiro, E.J., Fraga, C.A.M. (2009) Discovery of novel analgesic and anti-inflammatory 3-arylamine-imidazo [1,2-a]pyridine symbiotic prototypes. Bioorg. Med. Chem. 17:74–84.Search in Google Scholar

Ma, J.Z., Wang, H.B., Jiang, H. (2004) Synthesis and herbicidal activity of 1,4-dioxoquinoxaline-2-carbaldehyde acylhydrazones. Fine Chem. 21:309–312 (in Chinese).Search in Google Scholar

Ma, X.L., Huang, J.X., Duan, W.G., Mo, Q.J., Lin, G.S., Cen, B., Huang, Y. (2012a) Synthesis and herbicidal activities of novel α-terpinene-maleimide-based disulfamide compounds. Chin. J. Synth. Chem. 20:180–185 (in Chinese).Search in Google Scholar

Ma, X.L., Huang, J.X., Duan, W.G., Mo, Q.J., Lin, G.S., Huang, Y. (2012b) Synthesis and fungicidal activity of α-terpinene-maleimide-based acylhydrazone derivatives. Chin. J. Org. Chem. 32:1077–1083 (in Chinese).10.6023/cjoc1111171Search in Google Scholar

Ma, C.H., Cen, B., Duan, W.G., Ma, X.L., Qin, S., Lin, G.S., Qin, Y.N. (2013) Synthesis and biological activities of pinic acid-based dithioureas. Chem. Ind. For. Prod. 33:37–44 (in Chinese).Search in Google Scholar

Qian, H.F. (2004) Study on configuration reversions for (1S, 3R)-camphoric anhydride prepared from (1R, 3S)-camphoric acid. J. Nanjing Univ. Technol. 26:35–39 (in Chinese).Search in Google Scholar

Romeiro, N.C., Aguirre, G., Hernández, P., González, M., Cerecetto, H., Aldana, I., Pérez-Silanes, S., Monge, A., Barreiro, E.J., Lima, L.M. (2009) Synthesis, trypanocidal activity and docking studies of novel quinoxaline-N-acylhydrazones, designed as cruzain inhibitors candidates. Bioorg. Med. Chem. 17:641–652.Search in Google Scholar

Tributino, J.L.M., Duarte, C.D., Corrêa, R.S., Doriguetto, A.C., Ellena, J., Romeiro, N.C., Castro, N.G., Miranda, A.L.P., Barreiro, E.J., Fraga, C.A.M. (2009) Novel 6-methane-sulfonamide-3,4-methylenedioxyphenyl-N-acylhydrazones: orally effective anti-inflammatory drug candidates. Bioorg. Med. Chem. 17:1125–1131.Search in Google Scholar

Wang, D.L., Xu, J., Han, S., Gu, Z. (2008) Synthesis of some new hydrazone compounds containing azulene and their antibacterial activity. Chin. J. Org. Chem. 28:2016–2019 (in Chinese).Search in Google Scholar

Yang, J.G., Pan, F.Y., Li, J.M. (2005) Synthesis, characterization, crystal structure and antibacterial activities of copper(II) complex with 2′-(2-thienylidene)-hydroxybenzoyl-hydrazide. Chin. J. Inorg. Chem. 21:1593–1596 (in Chinese).Search in Google Scholar

Yang, J.F., Tao, J., Li, B.Q., Xue, M., Wei, W.Z. (2009) Synthesis and antibacterial activity of pyrazolyl hydrazone and its bis-heterocyclic compounds. Chin. J. Synth. Chem. 17:151–154 (in Chinese).Search in Google Scholar

Ye, Y., Zhao, Z.G., Liu, X.L., Li, Q.H. (2009) Microwave-assisted synthesis of indole-6-acylhydrazone and their antibacterial activities. Chin. J. Org. Chem. 29:993–997 (in Chinese).Search in Google Scholar

Zhang, Z.S., Wu, J.G., Deng, R.W. (1986) Preparation and properties of rare earth compounds from camphor acid. Lanzhou Univ. (Nat. Sci. Ed) 22:124–125 (in Chinese).Search in Google Scholar

Received: 2014-1-4
Accepted: 2014-3-4
Published Online: 2014-3-27
Published in Print: 2014-12-1

©2014 by De Gruyter

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