Combinatorial synthesis of a series of alkyl/alkenylacyloxy derivatives at the C-28 position of toosendanin as insecticidal agents

Combinatorial Chemistry and High Throughput Screening

Volumn 16, Issue 5, 2013, Pages 394-399

  Zhang, Junliang ^a   Qu, Huan ^a   Yu, Xiang ^a   Zhi, Xiaoyan ^a   Chen, Hui ^a   Xu, Hui ^a  

^a NORTHWEST A F UNIVERSITY   (China)

Author keywords

Botanical insecticide; C28 alkyl alkenylacyloxy; Combinatorial synthesis; Insecticidal activity; Toosendanin

Indexed keywords

ALKYL GROUP; FATTY ACID; INSECTICIDE;

ARTICLE; CONTROLLED STUDY; IN VIVO STUDY; INSECTICIDAL ACTIVITY; LARVA; MYTHIMNA SEPARATA; NONHUMAN; PRECURSOR; PRIORITY JOURNAL; SYNTHESIS;

ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUGS, CHINESE HERBAL; INSECTICIDES; INSECTS; LARVA; MOLECULAR STRUCTURE;

EID: 84878002465     PISSN: 13862073     EISSN: 18755402     Source Type: Journal    
DOI: 10.2174/1386207311316050004     Document Type: Article

References (18)

1. Nakai, Y.; Tepp, W.H.; Dickerson, T.J.; Johnson, E.A.; Janda, K.D. Function-oriented synthesis applied to the anti-botulinum natural product toosendanin. Bioorg. Med. Chem., 2009, 17, 1152-1157.
2. Nakai, Y.; Pellett, S.; Tepp, W.H.; Johnson, E.A.; Janda, K.D. Toosendanin: Synthesis of the AB-ring and investigations of its anti-botulinum properties (Part II). Bioorg. Med. Chem., 2010, 18, 1280-1287.
3. Akhtar, Y.; Isman, M.B. Comparative growth inhibitory and antifeedant effects of plant extracts and pure allelochemicals on four phytophagous insect species. J. Appl. Entomol., 2004, 128, 32- 38.
4. Chen, W.; Isman, M.B.; Chiu, S.F. Antifeedant and growthinhibitory effects of the limonoid toosendanin and melia-toosendan extracts on the variegated cutworm, peridroma-saucia (Lep, Noctuidae). J. Appl. Entomol., 1995, 119, 367-370.
5. Huang, R.C.; Okamura, H.; Iwagawa, T.; Tadera, K.; Nakatani, M., Azedarachin, C, A limonoid antifeedant from Melia azedarach. Phytochem., 1995, 38, 593-594.
6. Isman, M.B. Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Ann. Rev. Entomol., 2006, 51, 45-66.
7. Pavela, R. Possibilities of botanical insecticide exploitation in plant protection. Pest Technol., 2007, 1, 47-52.
8. Goel, M.; Dureja, P.; Rani, A.; Uniyal, P.L.; Laatsch, H. Isolation, characterization and antifungal activity of major constituents of the Himalayan lichen Parmelia reticulata Tayl. J. Agric. Food Chem., 2011, 59, 2299-2307.
9. Caballero-Gallardo, K.; Olivero-Verbel, J.; Stashenko, E.E. Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum Herbst. J. Agric. Food Chem., 2011, 59, 1690-1696.
10. Dayan, F.E.; Cantrell, C.L.; Duke, S.O. Natural products in crop protection. Bioorg. Med. Chem., 2009, 17, 4022-4034.
11. Xu, H.; Zhang, J.L. Natural products-based insecticidal agents 9. Design, semisynthesis and insecticidal activity of 28-acyloxy derivatives of toosendanin against Mythimna separata Walker in vivo. Bioorg. Med. Chem. Lett., 2011, 21, 1974-1977.
12. Buchstaller, H.P.; Anlauf, U. Parallel solution-phase synthesis of a 2-aminothiazole library including fully automated work-up. Comb. Chem. High Throughput Screen., 2011, 14, 104-108.
13. Woodard, S.S.; Jerome, K.D. Combinatorial synthesis of 3, 5- dimethylene substituted 1, 2, 4-triazoles. Comb. Chem. High Throughput Screen., 2011, 14, 132-137.
14. Sabbaghan, M.; Alidoust, M.; Hossaini, Z. A rapid, fourcomponent synthesis of functionalized thiazoles. Comb. Chem. High Throughput Screen., 2011, 14, 824-828.
15. Luesse, S.B.; Wells, G.; Miller, J.; Bolstad, E.; Bergmeier, S.C.; McMills, M.C.; Priestley, N.D.; Wright, D.L. Synthesis of a functionalized oxabicyclo [2.2.1]-heptene-based chemical library. Comb. Chem. High Throughput Screen., 2012, 15, 81-89.
16. Guo, Y.; Yan, Y.; Yu, X.; Wang, Y.; Xu, H. Synthesis and insecticidal activity of some novel fraxinellone-based esters. J. Agric. Food Chem., 2012, 60, 7016-7021.
17. Wang, Y.; Shao, Y.; Wang, Y.; Fan, L.; Yu, X.; Zhi, X.; Yang, C.; Qu, H.; Yao, X.; Xu, H. Synthesis and quantitative structureactivity relationship (QSAR) study of novel isoxazoline and oxime derivatives of podophyllotoxin as insecticidal agents. J. Agric. Food Chem., 2012, 60, 8435-8443.
18. Xu, H.; Wang, Q.T.; Guo, Y. Stereoselective synthesis of 4α- alkyloxy-2-α/β-bromopodophyllotoxin derivatives as insecticidal agents. Chem. Eur. J., 2011, 17, 8299-8303.