Synthesis and antiviral,insecticidal, and fungicidal activities of gossypol derivatives containing alkylimine,oxime or hydrazine moiety |
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| Affiliation: | 1. Department of Chemistry, Krieger School of Arts and Sciences, Johns Hopkins University, 3400 N. Charles St., Baltimore, MD 21218, USA;2. Institute for NanoBioTechnology, Johns Hopkins University, 3400 N. Charles St., Baltimore, MD 21218, USA;3. Department of Materials Science and Engineering, Whiting School of Engineering, Johns Hopkins University, 3400 N. Charles St., Baltimore, MD 21218, USA;1. H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan;2. Research Institute of Natural Products for Drug Discovery (RiND), Faculty of Pharmacy, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia;3. PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi 75280, Pakistan;4. Morales Consulting LLC, 11474 Perkins Street, Carmel, IN 46032, USA;5. Institute of Advance Research Studies in Chemical Sciences, University of Sindh Jamshoro, Hyderabad 76080, Pakistan;1. Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China;2. School of Chemistry & Chemical Engineering, Ankang University, Ankang 725000, Shaanxi Province, China;3. Shaanxi Key Laboratory of Natural Products & Chemical Biology, Northwest A&F University, Yangling 712100, Shaanxi Province, China;1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erzincan Binali Yildirim University, Yalnizbag, Erzincan, Turkey;2. Department of Biochemistry, Faculty of Pharmacy, Erzincan Binali Yildirim University, Yalnizbag, Erzincan, Turkey;1. State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China;2. College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, China;3. College of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China |
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| Abstract: | Gossypol is a part of the cotton plant’s defense system against pathogens and herbivorous insects. To discover gossypol analogs with broad spectrum and high activity, a series of gossypol alkylamine Schiff base, oxime and hydrazone derivatives were synthesised and bioassayed. The biological results indicated that most of these derivatives exhibited higher anti-TMV activity than gossypol. Interestingly, the activities of compounds 10, 15, 18, 20, 23 and 26 were much higher than that of ribavirin. Furthermore, compound 26, which was low toxicity to rat, showed better activity than control plant virus inhibitors in the field. Additionally, allyl amine Schiff base (9) displayed remarkable insecticidal activities against Mythimna separata, Helicoverpa armigera and Ostrinia nubilalis, whereas (pyridin-3-yl)methanamine Schiff base (13) showed excellent activity against Culex pipiens pallens. The fungicidal results revealed that all of compounds exhibited good activity against Physalospora piricola. |
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| Keywords: | Gossypol Schiff base Oxime Hydrazone Anti-TMV activity Structure–activity relationships |
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