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Synthesis of pyrazolo[1,5-a]pyrimidine derivatives and their antifungal activities against phytopathogenic fungi in vitro

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Abstract

5,6-Diarylpyrazolo[1,5-a]pyrimidines (3) and 6,7-diarylpyrazolo[1,5-a]pyrimidines (4) were chemoselectively synthesized by the condensation of isoflavone (1) and 3-aminopyrazole (2). 5,6-Diarylpyrazolo[1,5-a]pyrimidines (3) were obtained via microwave irradiation, and 6,7-diarylpyrazolo[1,5-a]pyrimidines (4) were obtained via conventional heating. In addition, the pyrimidine derivatives 3 and 4 were evaluated against five phytopathogenic fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani) using the mycelium growth rate method. Some of them were effective in inhibiting the growth of the five phytopathogenic fungi. For instance, 6,7-diarylpyrazolo[1,5-a]pyrimidines (4j) inhibited the growth of A. solani with an \(\hbox {IC}_{50}\) value of 17.11 \(\upmu \hbox {g}/\hbox {mL}\), and 6,7-diarylpyrazolo[1,5-a]pyrimidines (4h) inhibited the growth of both Cytospora sp. and F. solani with \(\hbox {IC}_{50}\) values of 27.32 and 21.04 \(\upmu \hbox {g}/\hbox {mL}\), respectively.

Graphical Abstract

A chemoselective synthesis of 5,6-pyrazolo[1,5-a]pyrimidines 3 derivatives in excellent yields was performed under microwave irradiation and 6,7-pyrazolo[1,5-a]pyrimidines 4 were also prepared using heating method. The antifungal properties of 3 and 4 were tested against Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani.

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Abbreviations

HRMS:

High-resolution mass spectrometry

TLC:

Thin-layer chromatography

mp:

Melting point

\(\hbox {IC}_{50}\) :

Half-maximal inhibitory concentration

SAR:

Structure–activity relationship

PDA:

Potato dextrose agar

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Acknowledgments

This research was supported by the National Natural Science Foundation of China (No. 21542002) and Innovation Funds of Graduate Programs of Shaanxi Normal University (No. 2016CBY002).

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Authors and Affiliations

  1. Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, People’s Republic of China

    Jin Zhang, Ju-Fang Peng, Ping Wang, Tao Wang & Zun-Ting Zhang

  2. Shaanxi Engineering Center of Bioresource Chemistry and Sustainable Utilization, College of Science, Northwest A&F University, Yangling, 712100, People’s Republic of China

    Yu-Bin Bai & Jin-Ming Gao

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  1. Jin Zhang
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  2. Ju-Fang Peng
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  3. Yu-Bin Bai
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  4. Ping Wang
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  5. Tao Wang
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  7. Zun-Ting Zhang
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Correspondence to Zun-Ting Zhang.

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Zhang, J., Peng, JF., Bai, YB. et al. Synthesis of pyrazolo[1,5-a]pyrimidine derivatives and their antifungal activities against phytopathogenic fungi in vitro. Mol Divers 20, 887–896 (2016). https://doi.org/10.1007/s11030-016-9690-y

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  • DOI: https://doi.org/10.1007/s11030-016-9690-y

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