Synthesis and bioactivity of N-benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] semicarbazide derivatives

Molecules

Volumn 15, Issue 6, 2010, Pages 4267-4282

  Cui, Zining ^a   Ling, Yun ^a   Li, Baoju ^b   Li, Yongqiang ^a   Rui, Changhui ^a   Cui, Jingrong ^c   Shi, Yanxia ^b   Yang, Xinling ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b INSTITUTE OF PLANT PROTECTION   (China)

^c PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Benzoylphenylurea; Bioactivity; Chitin synthesis inhibitors; Semicarbazide; Synthesis

Indexed keywords

ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; CARBAMOHYDRAZIDE; CARBANILAMIDE DERIVATIVE; INSECTICIDE; SEMICARBAZIDE DERIVATIVE; CARBAMYLHYDRAZINE;

ANIMAL; APHID; ARTICLE; CELL STRAIN HL 60; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE; X RAY DIFFRACTION; DRUG EFFECTS; HL 60 CELL LINE;

ANIMALS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; APHIDS; CELL LINE, TUMOR; CELL SURVIVAL; HL-60 CELLS; HUMANS; INSECTICIDES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PHENYLUREA COMPOUNDS; SEMICARBAZIDES; X-RAY DIFFRACTION;

EID: 77954303341     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15064267     Document Type: Article

References (32)

1. Cohen, E. Chitin synthesis and inhibition: A revisit. Pest Manag. Sci. 2001, 57, 946-950.
2. Ruiz-Herrera, J.; San-Blas, G. Chitin synthesis as a target for antifungal drugs. Curr. Drug Targets Infect. Disord. 2003, 3, 77-91.
3. Wellinga, K.; Mulder, R.; Dallen, J. V. Synthesis and laboratory evaluation of 1-(2, 6-disubtituted benzoyl)-3-phenylureas, a new class of insecticides. I. 1-(2, 5-Dichlorobenzoyl)-3-phenylureas. J. Agric. Food Chem. 1973, 21, 348-354.
4. Oberlander, H.; Silhacek, D. L. New Perspectives on the Mode of Action of Benzoylphenyl Urea Insecticides. In Insecticides with Novel Modes of Action: Mechanism and Application, 1st ed.; Ishaaya, I., Degheele, D., Eds.; Springer-Verlag: Berlin, Germany, 1998; pp. 92-105.
5. Oberlander, H.; Silhacek, D. L. Mode of action of insect growth regulators in Lepidopteran tissue culture. Pestic. Sci. 1998, 54, 300-302.
6. Qian, X. H. Quantitative studies on structure-activity relationship of sulfonylurea and benzoylphenylurea type pesticides and their substituents' bioisosterism using synthons' activity contribution. J. Agric. Food Chem. 1999, 47, 4415-4418.
7. Nakagawa, Y.; Kitahara, K.; Nishioka, T.; Iwamura, H.; Fujita, T. Quantitative structure-activity studies of benzoylphenylurea larvicides: I. Effect of substituents at aniline moiety against Chilo suppressalis walker. Pestic. Biochem. Physiol. 1984, 21, 309-325.
8. Tecle, B.; Ruzo, L. O.; Casida, J. E. Radiosynthesis of [benzoyl-3, 4, 5-3H]diflubenzuron by a route applicable to other high-potency Insect Growth Regulators. J. Agric. Food Chem. 1988, 36, 178-180.
9. Hashizume, B. Atabron 5E, a new IGR insecticide (chlorfluazuron). Jpn. Pestic. Inf. 1988, 58, 32-34.
10. Sbragia, R. J.; Johnson, G. W.; Karr, L. L.; Edwards, J. M.; Schneider, B. M. Preparation of benzoylphenylurea insecticides to control cockroaches, ants, fleas, and termites. WO 9819542, 1998;
11. [Chem. Abstr. 1998, 129, 13497].
12. Yoon, C.; Yang, J. O.; Kang, S. H.; Kim, G. H. Insecticidal properties of bistrifluron against sycamore lace bug, Corythucha ciliata (Hemiptera:Tingidae) . J. Pestic. Sci. 2008, 33, 44-50.
13. Grosscurt, A. C.; Van, H. R.; Wellinga, K. 1-Phenylcarbamoyl-2- pyrazolines, a new class of insecticides. 3. Synthesis and insecticidal properties of 3, 4-diphenyl-1-phenylcarbamoyl-2-pyrazolines. J. Agric. Food Chem. 1979, 27, 406-409.
14. Chen, L.; Wang, Q. M.; Huang, R. Q.; Mao, C. H.; Shang, J.; Bi, F. C. Synthesis and insecticidal evaluation of propesticides of benzoylphenylureas. J. Agric. Food Chem. 2005, 53, 38-41.
15. Chen, L.; Huang, Z. Q.; Wang, Q. M.; Shang, J.; Huang, R. Q.; Bi, F. C. Insecticidal benzoylphenylurea-S-carbamate: A new propesticide with two effects of both benzoylphenylureas and carbamates. J. Agric. Food Chem. 2007, 55, 2659-2663.
16. Sun, R. F.; Zheng, Y. L.; Chen, L.; Li, Y. Q.; Li, Q. S.; Song, H. B.; Huang, R. Q.; Bi, F. C.; Wang, Q. M. Design, synthesis and insecticidal activities of new N-benzoyl-N-phenyl-N-sulfenylureas. J. Agric. Food Chem. 2009, 57, 3661-3668.
17. Yang, X. L.; Ling, Y.; Wang, D. Q.; Chen, F. H. The synthesis and biological activity of N-phenyl-N-(5-phenyl-2-furoyl) ureas. Chin. J. Synth. Chem. 2002, 10, 510-512.
18. Yang, X. L.; Wang, D. Q.; Chen, F. H.; Ling, Y.; Zhang, Z. N.; Shang, Z. Z. Studies on the design, synthesis and biological activity of a novel type of acylurea compound. Chem. J. Chin. Univ. 1997, 18, 395-398.
19. Yang, X. L.; Wang, D. Q.; Chen, F. H.; Ling, Y.; Zhang, Z. N. The synthesis and larvicidal activity of N-aroyl-N-(5-aryl-2-furoyl) ureas. Pestic. Sci. 1998, 52, 282-286.
20. Li, Y.; Li, B. J.; Ling, Y.; Miao, H. J.; Shi, Y. X.; Yang, X. L. Synthesis and Fungicidal Activity of Aryl Carbamic Acid-5-aryl-2-furanmethyl Ester. J. Agric. Food Chem. 2010, 58, 3037-3042.
21. Ren, S. J.; Wang, R. B.; Komatsu, K.; Bonaz-Krause, P.; Zyrianov, Y.; McKenna, C. E.; Csipke, C.; Tokes, Z. A.; Lien, E. J. Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of new Schiff bases of hydroxysemicarbazide as potential antitumor agents. J. Med. Chem. 2002, 45, 410-419.
22. Nishat, N.; Ahamad, T.; Alshehri, S. M.; Parveen, S. Synthesis, characterization, and biocide properties of semicarbazide-formaldehyde resin and its polymer metal complexes. Eur. J. Med. Chem. 2010, 45, 1287-1294.
23. Speziale, A. J.; Smith, L. R. New and convenient synthesis of acyl isocyanates. J. Org. Chem. 1962, 27, 3742-3743.
24. Cui, Z. N.; Huang, J.; Li, Y.; Ling, Y.; Yang, X. L.; Chen, F. H. Synthesis and bioactivity of novel N, N'-diacylhydrazine derivatives containing furan (I). Chin. J. Chem. 2008, 26, 916-922
25. Bruker (1998) SMART. Bruker AXS Inc.: Madsion, WI, USA, 1998.
26. Sheldrick, G. M. (1997) SHELXS97 and SHELXL 97. University of Göttingen: Germany, 1997.
27. Bruker (1999) SAINT and SHELXTL. Bruker AXS Inc.: Madison, WI, USA, 1999.
28. Chen, N. C. Bioassay of Pesticides; Beijing Agricultural University Press: Beijing, China, 1991; pp. 161-162.
29. Chen, N. C. Bioassay of Pesticides; Beijing Agricultural University Press: Beijing, China, 1991; p. 54.
30. Denizot, F.; Lang, R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 1986, 89, 271-277.
31. Monks, A.; Scudiero, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langley, J.; Cronise, P. Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J. Natl. Cancer Inst. 1991, 83, 757-766.
32. Berkson, J. Application of the logistic function to bio-assay. J. Am. Statistical Assoc. 1944, 39, 357-365.