synthesis and antifungal activity of carabrone derivatives合成和抗真菌活性carabrone衍生品.pdf

Molecules 2010, 15, 6485-6492; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Communication Synthesis and Antifungal Activity of Carabrone Derivatives Jun-Tao Feng 1,* Zhi-Qing Ma 1, Jiang-Hua Li 1, Jun He 1, Hui Xu 1,2,* and Xing Zhang 1 , 1 Research and Development Center of Biorational Pesticide, College of Plant Protection, Northwest AF University, Yangling 712100, China 2 Laboratory of Pharmaceutical Design Synthesis, College of Sciences, Northwest AF University,Yangling 712100, China * Author to whom correspondence should be addressed; E-Mails: fengjt67@ (J.-T.F.); orgxuhui@ (H.X.) Received: 6 July 2010; in revised form: 11 August 2010 / Accepted: 23 August 2010 / Published: 16 September 2010 Abstract: Nine derivatives 6-14 of carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than 1. Structure-activity relationships (SAR) demonstrated that the γ-lactone was necessary for the antifungal activity of 1, and the substituents on the C-4 position of 1 could significantly affect the antifungal activity. Keywords: carabrone; structural modification; synthesis; antifungal activity 1. Introduction Carabrone (1, Figure 1), containing cyclopropane and sesquiterpene