Insecticidal lead identification by screening benzopyrano[4,3-c] pyrazol-3(2H)-ones library constructed from multiple-parallel synthesis under microwave irradiation |
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Authors: | Zhou Zhong-Zheng Yang Guang-Fu |
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Institution: | aKey Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China |
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Abstract: | A rapid library-generation via liquid-phase multiple-parallel synthesis of 2-(substituted)benzyl-1-benzopyrano4,3-c]pyrazol-3(2H)-ones, bearing two points of diversity, under microwave irradiation was successfully performed using chromenone-3-carboxylic acids as starting materials. Compared to an identical library generated by conventional parallel synthesis, microwave-assisted parallel synthesis dramatically decreased reaction times from an average of 16 h to 13 min, and the yields of products and intermediates were improved in most cases. A bioassay indicated that the compounds of the library exhibited excellent insecticidal activity against T. cinnabarinus at the dosage of 250 mg L?1, and some compounds still exhibited insecticidal activity when the dosage was reduced to 50 mg L?1. This shows that 2-(substituted) benzyl-1-benzopyrano4,3-c]pyrazol-3(2H)-ones might be used as lead structures for further optimization. To our knowledge, this is the first report about the application of solution-phase multiple-parallel synthesis under microwave irradiation to construct libraries of benzopyrano-4,3-c]pyrazol-3(2H)-ones with insecticidal activity. The coupling of microwave technology with liquid-phase parallel synthesis constitutes a novel and particularly attractive avenue for the rapid generation of structurally diverse libraries for lead discovery. |
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Keywords: | Microwave-assisted parallel synthesis Benzopyrano[4 3-c]pyrazol-3(2H)-ones Combinatorial chemistry Insecticidal activity Lead structure |
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