Design, synthesis, fungicidal activities and structure–activity relationship studies of (−)-borneol derivatives containing 2-aryl-thiazole scaffold. (1st August 2021)

• Record Type: Journal Article
• Authors: Huang, Danling; Zheng, Shumin; Zhang, Tianyuan; Cheng, Yong-Xian
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 45(2021)
• Publication Date: 2021-08-01
• Subjects: Borneol derivatives -- Thiazole -- Synthesis -- Fungicidal activity -- Structure-activity relationship; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2021.128006
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: Abstract: A series of (-)-borneol derivatives containing 2-aryl-thiazole scaffold were designed, synthesized, and characterized by 1 H NMR, 13 C NMR, and HRMS. The fungicidal activities of these novel compounds against Fusarium oxysporum, Magnaporthe grisea, Botrytis cinerea, and Penicillium digitatum were evaluated. The results indicated that (1S, 2R, 4S)-1, 7, 7-trimethylbicyclo[2.2.1]heptan-2-yl(Z)-4-oxo-4-(((2-phenylthiazol-4-yl)methyl)amino)but-2-enoate (6a) displayed potential fungicidal activities with broad spectrum. Especially, 6a exhibited an IC50 value of 48.5 mg/L against P. digitatum, which has higher fungicidal activity than commercial products hymexazol and amicarthiazol. Moreover, (1S, 2R, 4S)-1, 7, 7-trimethylbicyclo[2.2.1]heptan-2-yl-4-oxo-4-(((2-phenylthiazol-4-yl)methyl)amino)butanoate (5a) possesses an IC50 value of 24.3 mg/L against B. cinerea, comparable to hymexazol and far superior to amicarthiazol. Furthermore, the superficial structure–activity relationship was discussed, which might be helpful for discovering novel fungicides.