Diacylhydrazine derivatives as novel potential chitin biosynthesis inhibitors: Design, synthesis, and structure-activity relationship

European Journal of Medicinal Chemistry

Volumn 44, Issue 7, 2009, Pages 2985-2993

  Ke, Shaoyong ^a   Qian, Xuhong ^a   Liu, Fengyi ^b   Wang, Ni ^b   Fan, Feng ^a   Li, Zhong ^a   Yang, Qing ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Chitin biosynthesis; Diacylhydrazine; Potential inhibitors; QSAR

Indexed keywords

2 CHLORO N' (2 METHOXYBENZOYL) N' (NONAN 5 YL)BENZOHYDRAZIDE; 2 CHLORO N' (3 FLUOROBENZOYL) N' (NONAN 5 YL)BENZOHYDRAZIDE; 2 CHLORO N' (4 ETHYLBENZOYL) N (NONAN 5 YL)BENZOHYDRAZIDE; 2 CHLORO N' (4 FLUOROBENZOYL) N' (NONAN 5 YL)BENZOHYDRAZIDE; 2,3,5 TRIFLUORO 4 METHOXY N (NONAN 5 YL) N' (3,4,5 TRIMETHOXYBENZOYL)BENZOHYDRAZIDE; 2,4 DICHLORO N' (3,5 DIMETHYLBENZOYL) N' (NONAN 5 YL)BENZOHYDRAZIDE; CHITIN; HYDRAZINE DERIVATIVE; N' (2 CHLOROACETYL) 4 ETHYL N' (NONAN 5 YL)BENZOHYDRAZIDE; N' (2 CHLOROBENZOYL) 3,4,5 TRIMETHOXY N' (NONAN 5 YL)BENZOHYDRAZIDE; N' (2 CHLOROBENZOYL) 3,5 DIMETHYL N (NONAN 5 YL)BENZOHYDRAZIDE; N' (3,5 DIMETHYLBENZOYL) 3,4,5 TRIMETHOXY N' (NONAN 5 YL)BENZOHYDRAZIDE; N' (4 CHLOROBENZOYL) 2 METHOXY N (NONAN 5 YL)BENZOHYDRAZIDE; N' (4 CHLOROBENZOYL) 3,5 DIMETHYL N (NONAN 5 YL)BENZOHYDRAZIDE; N' (4 ETHYLBENZOYL) 2 METHOXY N (NONAN 5 YL)BENZOHYDRAZIDE; N' (4 ETHYLBENZOYL) 2,3,5 TRIFLUORO 4 METHOXY N (NONAN 5 YL)BENZOHYDRAZIDE; N' (4 ETHYLBENZOYL) 3,5 DIMETHYL N (NONAN 5 YL)BENZOHYDRAZIDE; N' (4 ETHYLBENZOYL) 3,5 DIMETHYL N' (NONAN 5 YL)BENZOHYDRAZIDE; N' (4 ETHYLBENZOYL) N (NONAN 5 YL)BENZO[D][1,3] DIOXOLE 5 CARBOHYDRAZIDE; N' BENZOYL 2 CHLORO N' (NONAN 5 YL)BENZOHYDRAZIDE; N' BENZOYL 3 METHOXY N' (NONAN 5 YL)BENZOHYDRAZIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONTROLLED STUDY; INFRARED SPECTROSCOPY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SACCHAROMYCES CEREVISIAE; SYNTHESIS;

CHITIN; DRUG DESIGN; HYDRAZINES; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; SACCHAROMYCES CEREVISIAE; SPECTRUM ANALYSIS;

EID: 67349113184     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.01.004     Document Type: Article

References (38)

1. Gooday G.W. J. Gen. Microbiol. 99 (1977) 1-11
2. Cohen E. Arch. Insect Biochem. Physiol 22 (1993) 245-261
3. Merzendorfer H., and Zimoch L. J. Exp. Biol. 206 (2003) 4393-4412
4. Maertens J.A., and Boogaerts M.A. Curr. Pharm. Des. 6 (2000) 225-239
5. Kang T.H., Hwang E.I., Yun B.S., Park K.D., Kwon B.M., Shin C.S., and Kim S.U. Biol. Pharm. Bull. 30 (2007) 598-602
6. Tellam R.L., Vuocolo T., Johnson S.E., Jarmey J., and Pearson R.D. Eur. J. Biochem. 267 (2000) 6025-6042
7. Merzendorfer H. J. Comp. Physiol. B 176 (2006) 1-15
8. van Eck W.H. Insect Biochem 9 (1979) 295-300
9. Ruiz-Herrera J., and San-Blas G. Curr. Drug Targets - Infect. Disord. 3 (2003) 77-91
10. Behr J.-B. Curr. Med. Chem. - Anti-Infective Agents 2 (2003) 173-189
11. Sheets J.J. In: Krämer W., and Schimer U. (Eds). Modern Crop Protection Compounds (2007), Wiley-VCH Verlag GmbH & Co. KgaA, Weinheim 813-824
12. Tunaz H., and Uygun N. Turk. J. Agric. For. 28 (2004) 377-387
13. Wing K.D. Science 241 (1988) 467-469
14. Chandler L.D., Pair S.D., and Harrison W.E. J. Econ. Entomol. 85 (1992) 1099-1103
15. Sawada Y., Yanai T., Nakagawa H., Tsukamoto Y., Yokoi S., Yanagi M., Toya T., Sugizaki H., Kato Y., Shirakura H., Watanebe T., Yajima Y., Kodama S., and Masui A. Pest Manage. Sci. 59 (2003) 25-35
16. Sawada Y., Yanai T., Nakagawa H., Tsukamoto Y., Yokoi S., Yanagi M., Toya T., Sugizaki H., Kato Y., Shirakura H., Watanabe T., Yajima Y., Kodama S., and Masui A. Pest Manage. Sci. 59 (2003) 36-48
17. Sawada Y., Yanai T., Nakagawa H., Tsukamoto Y., Tamagawa Y., Yokoi S., Yanagi M., Toya T., Sugizaki H., Kato Y., Shirakura H., Watanabe T., Yajima Y., Kodama S., and Masui A. Pest Manage. Sci. 59 (2003) 49-57
18. Carlson G.R., Dhadialla T.S., Hunter R., Jansson R.K., Jany C.S., Lidert Z., and Slawecki R.A. Pest Manage. Sci. 57 (2001) 115-119
19. Heller J.J., Mattioda H., Klein E., and Sagenmuller A. Brighton Conf. Pest Dis. 25 (1992) 59-65
20. Yanagi M., Watanabe T., Masui A., Yokoi S., Tsukamoto Y., and Ichinose R. Brighton Conf. Pest Dis. 2A-2 (2000) 27-32
21. Hsu A.C.-T. In: Baker D.R., Fenyes J.G., and Moberg W.K. (Eds). Synthesis and Chemistry of Agrochemicals II. ACS Symposium Series vol. 443 (1991), American Chemical Society, Washington, D.C 478-490
22. Cao S., Qian X., and Song G. Can. J. Chem. 79 (2001) 272-278
23. Toya T., Yamaguchi K., and Endo Y. Bioorg. Med. Chem. 10 (2002) 953-961
24. Mao C., Wang Q., Huang R., Bi F., Chen L., Liu Y., and Shang J. J. Agric. Food Chem. 52 (2004) 6737-6741
25. Nakagawa Y. J. Pestic. Sci. 32 (2007) 135-136
26. Zhao P., Li J., and Yang G. Bioorg. Med. Chem. 15 (2007) 1888-1895
27. Shang J., Liu Y., Huang R., Bi F., and Wang Q. Heteroat. Chem. 18 (2007) 631-636
28. Zhao Q., Shang J., Liu Y., Wang K., Bi F., Huang R., and Wang Q. J. Agric. Food Chem. 55 (2007) 9614-9619
29. Mao C., Wang K., Wang Z., Ou X., Huang R., Bi F., and Wang Q. Bioorg. Med. Chem. 16 (2008) 488-494
30. Zhao Q., Shang J., Huang Z., Wang K., Bi F., Huang R., and Wang Q. J. Agric. Food Chem. 56 (2008) 5254-5259
31. Dinan L., and Hormann R.E. In: Gilbert L.I., Iatrou K., and Gill S.S. (Eds). Comprehensive Insect Molecular Science vol. 3 (2005), Elsevier Pergamon, New York 198-236
32. Wheelock C.E., Nakagawa Y., Harada T., Oikawa N., Akamatsu M., Smagghe G., Stefanou D., Iatrou K., and Swevers L. Bioorg. Med. Chem. 14 (2006) 1143-1159
33. Ke S., Liu F., Wang N., Yang Q., and Qian X. Bioorg. Med. Chem. Lett. 19 (2009) 332-335
34. Ke S., Qian X., Liu F., Wang N., Yang Q., and Li Z. Eur. J. Med. Chem. (2008) 10.1016/j.ejmech.2008.10.015
35. Lucero H.A., Kuranda M.J., and Bulik D.A. Anal. Biochem. 305 (2002) 97-105
36. Zou X., Jin G., and Zhang Z. J. Agric. Food Chem. 50 (2002) 1451-1454
37. Tian Z., Shao X., Li Z., Qian X., and Huang Q. J. Agric. Food Chem. 55 (2007) 2288-2292
38. Fan F., Li Z., Xu X., and Qian X. QSAR Comb. Sci. 26 (2007) 737-743