Synthesis and Biological Activity of Pyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine Derivatives

doi:10.11944/j.issn.1000-0518.2017.11.160502

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (11): 1279-1286.DOI: 10.11944/j.issn.1000-0518.2017.11.160502

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Synthesis and Biological Activity of Pyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine Derivatives

LIU Jianchao^a,REN Qingyun^b^*,HE Hongwu^a^*()

^aCollege of Chemistry,Central China Normal University,Wuhan,430079,China
^bAnti-infection Innovation Department,New Drug Research Institute,HEC,Dongguan,Guangdong 523871,China

Received:2016-12-09 Accepted:2017-02-24 Published:2017-11-08 Online:2017-11-08
Contact: REN Qingyun,HE Hongwu
Supported by:
Supported by the National Natural Science Fundation of China(No.21172090, No.31000867), the Program for Changjiang Scholars and Innovatives Research Team in University(No.IRT0953)

Abstract

Abstract:

A series of new 2-substituted-3,8-diphenyl-5-aryl-6-methyl-5,8-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine derivatives was designed and synthesized via tandem aza-Wittig reaction. The structures of target compounds were confirmed by ¹H NMR, IR spectra and elemental analysis. The structure of 2-dipropylamino-3,8-diphenyl-5-(4-methylphenyl)-6-methyl-5,8-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-4(3H)-one was determined by single crystal X-ray diffraction. The results of preliminary bioassay indicate that some compounds possess good inhibition activities against Botrytis cinereapers at a dosage of 5.0×10^-5 g/mL, and the inhibition rates against Botrytis cinereapers are above 90%. Target compounds possess no insecticidal activity against Nilaparvatalegen, but show obvious insecticidal activity against Mythimaseparata, and the inhibihition rates against Mythimaseparata are above 60%.

Key words: Aza-Wittig reaction, pyrazolopyrimidine, pyranopyrimidine, biological activity

LIU Jianchao, REN Qingyun, HE Hongwu. Synthesis and Biological Activity of Pyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine Derivatives[J]. Chinese Journal of Applied Chemistry, 2017, 34(11): 1279-1286.

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Synthesis and Biological Activity of Pyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidine Derivatives

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