Design, synthesis and antifungal activities of novel pyrrole- and pyrazole-substituted coumarin derivatives.

We synthesized a series of novel pyrrole- and pyrazole-substituted coumarin derivatives and evaluated their antifungal activity against six phytopathogenic fungi in vitro. The primary assay results demonstrated that some designed compounds displayed potent activities. Among them, compounds 5g, 6a, 6b, 6c, 6d and 6h exhibited more effective control than Osthole against Cucumber anthrax and Alternaria leaf spot. Furthermore, compound 5g displayed stronger antifungal activity against Rhizoctorzia solani (EC50 = 15.4 µg/mL) than positive control Osthole (EC50 = 67.2 µg/mL).

Design, Synthesis and Antifungal Activity of Coumarin Ring-Opening Derivatives.

Based on our initial design, we synthesized two series of coumarin ring-opening derivatives by the reactions of hydrolysis and methylation. Results of antifungal screening in vitro showed that the target compounds exhibited potent activity against the six common pathogenic fungi. Compounds 6b, 6e, 6g, 6i, 7b and 7c were identified as the most active ones, and the EC50 values of these active compounds were further tested. Compared to the commonly used fungicide Azoxystrobin (0.0884 µM), compounds 6b (0.0544 µM) and 6e (0.0823 µM) displayed improved activity against Botrytis cinerea.

Microwave-assisted synthesis and antifungal activity of novel fused Osthole derivatives.

Based on the microwave-assisted synthetic protocol developed in our previous work, we have synthesized a series of novel furo[3,2-c]coumarins as fused Osthole derivatives, via the reaction of 4-hydroxycoumarins and ß-ketoesters catalyzed by DMAP. All the target compounds were evaluated in vitro for their antifungal activity against six phytopathogenic fungi, some compounds exhibited potential activity in the primary assays. Especially compounds 6c, 7b, 8b and 8c (shown in Fig. 1) were the most active ones, EC50 values of these four compounds against Colletotrichum capsica, Botrytis cinerea and Rhizoctonia solani were further investigated. 6c was identified as the most promising candidate with the EC50 value at 0.110 µM against Botrytis cinerea and 0.040 µM against Colletotrichum capsica, respectively, representing better antifungal activity than that of the commonly used fungicide Azoxystrobin.