Synthesis and antiviral, insecticidal, and fungicidal activities of gossypol derivatives containing alkylimine, oxime or hydrazine moiety. Issue 3 (1st February 2016)

• Record Type: Journal Article
• Authors: Li, Ling; Li, Zheng; Wang, Kailiang; Liu, Yuxiu; Li, Yongqiang; Wang, Qingmin
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 3(2016)
• Page Start: 474
• Page End: 483
• Publication Date: 2016-02-01
• Subjects: Gossypol -- Schiff base -- Oxime -- Hydrazone -- Anti-TMV activity -- Structure–activity relationships; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2015.08.015
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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 compounds10, 15, 18, 20, 23 and26 were much higher than that of ribavirin. Furthermore, compound26, 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 .