Natural product-based semisynthesis and biological evaluation of thiol/amino-Michael adducts of xanthatin derived from Xanthium strumarium as potential pesticidal agents

• Published in: Bioorganic chemistry Vol. 97; pp. 103696 - 103706
• Main Authors: Zhi, Xiao-yan, Jiang, Ling-yun, Li, Ting, Song, Li-li, Wu, Li-juan, Cao, Hui, Yang, Chun
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.04.2020; Elsevier
• Subjects: Amination; Antifungal activity; Biochemistry & Molecular Biology; Botrytis - drug effects; Chemistry; Chemistry, Organic; Fungicides, Industrial - chemical synthesis; Fungicides, Industrial - chemistry; Fungicides, Industrial - toxicity; Furans - chemical synthesis; Furans - chemistry; Furans - toxicity; Larvicidal activity; Life Sciences & Biomedicine; Models, Molecular; Natural products-based pesticides; Ovicidal activity; Physical Sciences; Plant Diseases - microbiology; Plant Diseases - prevention & control; Science & Technology; Sulfhydryl Compounds - chemical synthesis; Sulfhydryl Compounds - chemistry; Sulfhydryl Compounds - toxicity; Xanthatin; Xanthium - chemistry; Xanthium strumarium; Antifungal activity; Larvicidal activity; Ovicidal activity; Natural products-based pesticides; Xanthatin; Xanthium strumarium; DESIGN; L; DISCOVERY; SESQUITERPENE LACTONES; XANTHANOLIDES; ANTICANCER; ANTIFUNGAL ACTIVITIES; AMINO-DERIVATIVES

[Display omitted] •Forty-nine Michael-type thiol/amino adducts of xanthatin were synthesized.•Compounds 2c, 2h, 2i, and 2t exhibited excellent antifungal activity.•Derivatives 2b, 7g, and 7h demonstrated significant ovicidal activity.•The structure-activity relationships (SARs) were also discussed....