Design, synthesis, antifungal activities and 3D-QSAR of new N,N'-diacylhydrazines containing 2,4-dichlorophenoxy moiety

International Journal of Molecular Sciences

Volumn 14, Issue 11, 2013, Pages 21741-21756

  Sun, Na Bo ^a   Shi, Yan Xia ^b   Liu, Xing Hai ^c   Ma, Yi ^d   Tan, Cheng Xia ^c   Weng, Jian Quan ^c   Jin, Jian Zhong ^a   Li, Bao Ju ^b  

^a ZHEJIANG SHUREN UNIVERSITY   (China)

^b INSTITUTE OF PLANT PROTECTION   (China)

^c ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

^d NANKAI UNIVERSITY   (China)

Author keywords

Antifungal activity; N,N' diacylhydrazines; Synthesis; Three dimensional quantitative structure activity relationships (3D QSAR)

Indexed keywords

1 CYANO N' [2 (2,4 DICHLOROPHENOXY)ACETYL]CYCLOPROPANECARBOHYDRAZIDE; 2 (2,4 DICHLOROPHENOXY) N' [2 (2,4 DICHLOROPHENOXY)ACETYL]ACETOHYDRAZIDE; 2 (2,4 DICHLOROPHENOXY) N' [2 (2,4 DICHLOROPHENOXY)ACETYL]PROPANEHYDRAZIDE; 2 CHLORO N' [2 (2,4 DICHLOROPHENOXY)ACETYL]BENZOHYDRAZIDE; 2,4 DICHLORO N' [2 (2,4 DICHLOROPHENOXY)ACETYL]BENZOHYDRAZIDE; 2,4 DICHLOROPHENOXYACETIC ACID; 3 CHLORO N' [2 (2,4 DICHLOROPHENOXY)ACETYL]BENZOHYDRAZIDE; 4 CHLORO N' [2 (2,4 DICHLOROPHENOXY)ACETYL]BENZOHYDRAZIDE; ANTIFUNGAL AGENT; CHLOROTHALONIL; HYDRAZINE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL] 2 FLUOROBENZOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL] 2 METHOXYBENZOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL] 3 METHYLBENZOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL] 4 IODOBENZOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL] 4 METHOXYBENZOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL] 4 NITROBENZOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL] 5 METHYLISOXAZOLE 4 CARBOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]BENZOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]BUTYROHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]CYCLOPROPANECARBOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]FURAN 3 CARBOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]HEXA 2,4 DIENEHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]ISOBUTYROHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]ISONICOTINOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]NICOTINOHYDRAZIDE; N' [2 (2,4 DICHLOROPHENOXY)ACETYL]PENTANEHYDRAZIDE; N,N' DIACYLHYDRAZINE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; ASCOMYCETES; CLADOSPORIUM CUCUMERINUM; COLLETOTRICHUM; COLLETOTRICHUM ORBICULARE; COMPARATIVE MOLECULAR FIELD ANALYSIS; CONTROLLED STUDY; CORYNESPORA CASSIICOLA; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ERYSIPHE CICHORACEARUM; HERBICIDAL ACTIVITY; MYCELIAL GROWTH; NONHUMAN; PLEOSPORALES; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SCLEROTINIA SCLEROTIORUM;

ANTIFUNGAL AGENTS; CHLOROPHENOLS; FUNGI; HUMANS; HYDRAZINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84887150634     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms141121741     Document Type: Article

References (38)

1. Kim, B. Y.; Willbold, S.; Kulik, A.; Helaly, S. E.; Zinecker, H.; Wiese, J.; Imhoff, J. F.; Goodfellow, M.; Sussmuth, R. D.; Fiedler, H. P. Elaiomycins B and C, novel alkylhydrazides produced by Streptomyces sp. BK 190. J. Antibiot. 2011, 64, 595-597.
2. Shoeb, M.; MacManus, S. M.; Jaspars, M.; Trevidu, J.; Nahar, L.; Kong-Thoo-Lin, P.; Sarker, S. D. Montamine, a unique dimeric indole alkaloid, from the seeds of Centaurea montana (Asteraceae), and its in vitro cytotoxic activity against the CaCo2 colon cancer cells. Tetrahedron 2006, 62, 11172-11177.
3. Zheng, J.; Liu, C.; Sawaya, M. R.; Vadla, B.; Khan, S.; Woods, R. J.; Eisenberg, D.; Goux, W. J.; Nowick, J. S. Macrocyclic β-sheet peptides that inhibit the aggregation of a tau-protein-derived hexapeptide. J. Am. Chem. Soc. 2011, 133, 3144-3157.
4. Zhao, Q. Q.; Ou, X. M.; Huang, Z. Q.; Bi, F. C.; Huang, R. Q.; Wang, Q. M. Synthesis and insecticidal activities of novel N-sulfenyl-N'-tert-butyl-N, N'-diacylhydrazines. 3. N-(alkyldithio), N-(aminothio), and N, N-dithio derivatives. J. Agric. Food Chem. 2008, 56, 10799-10804.
5. Zhao, H.; Neamati, N.; Sunder, S.; Hong, H. X.; Wang, S. M.; Milne, G. W. A.; Pommier, Y.; Burke, T. R. Hydrazide-containing inhibitors of HIV-1 integrase. J. Med. Chem. 1997, 40, 937-941.
6. Liu, X. H.; Shi, Y. X.; Ma, Y.; He, G. R.; Dong, W. L.; Zhang, C. Y.; Wang, B. L.; Wang, S. H.; Li, B. J.; Li, Z. M. Synthesis of some N, N'-diacylhydrazine derivatives with radical-scavenging and antifungal activity. Chem. Biol. Drug Des. 2009, 73, 320-327.
7. Li, W.; Gao, L. M.; Zhang, Y. M.; Wei, T. B. Synthesis and biological activity of 1-[2-(1-phenyl-1H-tetrazole-5-yl)-thio] acetylhydrazine derivatives (in Chinese). Huaxue Shiji 2008, 30, 89-91.
8. Liu, X. H.; Pan, L.; Ma, Y.; Weng, J. Q.; Tan, C. X.; Li, Y. H.; Shi, Y. X.; Li, B. J.; Li, Z. M.; Zhang, Y. G. Design, synthesis, biological activities, and 3D-QSAR of new N, N'-diacylhydrazines containing 2-(2, 4-dichlorophenoxy)propane moiety. Chem. Biol. Drug Des. 2011, 78, 689-694.
9. Liu, H.; Wang, H. Q.; Liu, Z. J. Synthesis and herbicidal activity of novel pyrazolo[3, 4-d]pyrimidin-4-one derivatives containing aryloxyphenoxypropionate moieties. Bioorg. Med. Chem. Lett. 2007, 17, 2203-2209.
10. Han, L.; Gao, J. R.; Li, Z. M.; Zhang, Y.; Guo, W. M. Synthesis of new plant growth regulator: N-(Fatty acid) O-aryloxyacetyl ethanolamine. Bioorg. Med. Chem. Lett. 2007, 17, 3231-3234.
11. Zhang, H.; Zan, J. H.; Yu, G. Y.; Jiang, M.; Liu, P. X. A combination of 3D-QSAR, molecular docking and molecular dynamics simulation studies of benzimidazole-quinolinone derivatives as iNOS inhibitors. Int. J. Mol. Sci. 2012, 13, 11210-11227.
12. Lu, X. Y.; Lv, M.; Huang, K.; Ding, K.; You, Q. D. Pharmacophore and molecular docking guided 3D-QSAR study of bacterial enoyl-ACP reductase (FabI) inhibitors. Int. J. Mol. Sci. 2012, 13, 6620-6638.
13. Ouyang, L.; He, G.; Huang, W.; Song, X. R.; Wu, F. B.; Xiang, M. L. Combined structure-based pharmacophore and 3D-QSAR studies on phenylalanine series compounds as TPH1 inhibitors. Int. J. Mol. Sci. 2012, 13, 5348-5363.
14. Hansch, C.; Fujita, T. ρ-σ-π analysis. Method for correlation of biological activity chemical structure. J. Am. Chem. Soc. 1964, 86, 1616-1626.
15. Free, S. M.; Wilson, J. W. A mathematical contribution to structure-activity studies. J. Med. Chem. 1964, 7, 395-399.
16. Putz, M. V.; Lazea, M.; Putz, A. M.; Duda-Seiman, C. Introducing catastrophe-QSAR. Application on modeling molecular mechanisms of pyridinone derivative-type HIV non-nucleoside reverse transcriptase inhibitors. Int. J. Mol. Sci. 2011, 12, 9533-9569.
17. Putz, M. V.; Ionascu, C.; Putz, A. M.; Ostafe, V. Alert-QSAR. Implications for electrophilic theory of chemical carcinogenesis. Int. J. Mol. Sci. 2011, 12, 5098-5134.
18. Putz, M. V.; Lazea, M.; Sandjo, L. P. Quantitative structure inter-activity relationship (QSInAR). Cytotoxicity study of some hemisynthetic and isolated natural steroids and precursors on human fibrosarcoma cells HT1080. Molecules 2011, 16, 6603-6620.
19. Putz, M. V.; Putz, A. M.; Lazea, M.; Ienciu, L.; Chiriac, A. Quantum-SAR extension of the spectral-SAR algorithm. Application to polyphenolic anticancer bioactivity. Int. J. Mol. Sci. 2009, 10, 1193-1214.
20. De Souza, S. D.; de Souza, A. M. T.; de Sousa, A. C. C.; Sodero, A. C. R.; Cabral, L. M.; Albuquerque, M. G.; Castro, H. C.; Rodrigues, C. R. Hologram QSAR models of 4-[(diethylamino)methyl]-phenol inhibitors of acetyl/butyrylcholinesterase enzymes as potential anti-alzheimer agents. Molecules 2012, 17, 9529-9539.
21. Putz, M. V. Residual-QSAR. Implications for genotoxic carcinogenesis. Chem. Cent. J. 2011, 5, 1-11.
22. Putz, M. V.; Dudaş, N. A. Determining chemical reactivity driving biological activity from SMILES transformations: The bonding mechanism of anti-HIV pyrimidines. Molecules 2013, 18, 9061-9116.
23. Putz, M. V.; Dudaş, N. A. Variational principles for mechanistic quantitative structure-activity relationship (QSAR) studies: Application on uracil derivatives' anti-HIV action. Struct. Chem. 2013, doi: 10. 1007/s11224-013-0249-6.
24. Putz, M. V.; Putz, A. M.; Barou, R. Spectral-SAR realization of OECD-QSAR principles. Int. J. Chem. Model. 2011, 3, 173-190.
25. Liu, X. H.; Weng, J. Q.; Tan, C. X. Microwave synthesis and biological activity of hydrazone derivatives containing 1, 2, 3-thiadiazole. Asian J. Chem. 2011, 23, 4064-4066.
26. Liu, X. H.; Chen, P. Q.; Wang, B. L.; Li, Y. H.; Wang, S. H.; Li, Z. M. Synthesis, bioactivity, theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor. Bioorg. Med. Chem. Lett. 2007, 17, 3784-3788.
27. Xue, Y. L.; Liu, X. H.; Zhang, Y. G. Synthesis, crystal structure and biological activity of 1-cyano-N-phenylcyclopropanecarboxamide. Asian J. Chem. 2012, 24, 1571-1574.
28. Xue, Y. L.; Zhang, Y. G.; Liu, X. H. Synthesis, crystal structure and biological activity of 1-Cyano-N-(4-bromophenyl)cyclopropanecarboxamide. Asian J. Chem. 2012, 24, 3016-3018.
29. Wu, R.; Zhu, C.; Du, X. J.; Xiong, L. X.; Yu, S. J.; Liu, X. H.; Li, Z. M.; Zhao, W. G. Synthesis, crystal structure and larvicidal activity of novel diamide derivatives against Culex pipiens. Chem. Cent. J. 2012, 6, 1-5.
30. Weng, J. Q.; Wang, L.; Liu, X. H. Synthesis, crystal structure and herbicidal activity of a 1, 2, 4-triazol-5 (4H)-one derivative. J. Chem. Soc. Pak. 2012, 34, 1248-1252.
31. Xue, Y. L.; Zhang, Y. G.; Liu, X. H. Synthesis, crystal structure and biological activity of 1-cyano-N-(2, 4-dichlorophenyl)cyclopropanecarboxamide. Asian J. Chem. 2012, 24, 5087-5089.
32. Cui, C.; Wang, Z. P.; Du, X. J.; Wang, L. Z.; Yu, S. J.; Liu, X. H.; Li, Z. M.; Zhao, W. G. Synthesis and antiviral activity of hydrogenated ferulic acid derivatives. J. Chem. 2013, 2013, 269434: 1-269434: 5.
33. Sun, N. B.; Liu, X. H.; Weng, J. Q.; Tan, C. X. An unexpected product N-{3-[(2-fluorobenzyl)thio]-5-methyl-4H-1, 2, 4-triazol-4-yl}acetimidamide: Synthesis and structure analysis. J. Chem. Soc. Pak. 2013, 35, 499-502.
34. Huang, Z. Q.; Zhao, Q. Q.; Huang, R. Q.; Wang, Q. M. Design and synthesis of novel N'-tert-butyl-N'-substitutedbenzoyl-N-[dihydrobenzofuran(chroman)]carbohydrazide derivatives as potential insect growth regulators. Lett. Org. Chem. 2009, 6, 29-36.
35. Zhao, Q. Q.; Shang, J.; Huang, Z. Q.; Wang, K. Y.; Bi, F.; Huang, R. Q.; Wang, Q. M. Synthesis and insecticidal activities of novel N-Sulfenyl-N'-tert-butyl-N, N'-diacylhydrazines. 2. N-Substituted phenoxysulfenate derivatives. J. Agr. Food Chem. 2008, 56, 5254-5259.
36. SYBYL, version 6. 91; Tripos Inc.: St. Louis, MO, USA, 2004.
37. Liu, X. H.; Shi, Y. X.; Ma, Y.; Zhang, C. Y.; Dong, W. L.; Pan, L.; Wang, B. L.; Li, B. J.; Li, Z. M. Synthesis, antifungal activities and 3D-QSAR study of N-(5-substituted-1, 3, 4-thiadiazol-2-yl) cyclopropanecarboxamides. Eur. J. Med. Chem. 2009, 44, 2782-2786.
38. Tan, C. X.; Shi, Y. X.; Weng, J. Q.; Liu, X. H.; Li, B. J.; Zhao, W. G. Synthesis and antifungal activity of 1, 2, 4-triazole derivatives containing cyclopropane moiety. Lett. Drug Des. Discov. 2012, 9, 431-435.