吡唑并[4',3':5,6]吡喃并[2,3-d]嘧啶化合物的合成与生物活性

doi:10.11944/j.issn.1000-0518.2017.11.160502

摘要/Abstract

摘要：

应用串联氮杂Wittig反应设计合成了一系列新的2-烷氨(芳氧)基-3,8-二苯基-5-芳基-6-甲基-5,8-二氢-4H-吡唑并[4',3':5,6]吡喃并[2,3-d]嘧啶-4(3H)-酮衍生物。通过氢核磁共振谱仪(¹H NMR)、傅里叶变换红外光谱仪(FTIR)和元素分析等方法对所合成的化合物进行了结构表征,用X射线单晶衍射确证了化合物2-二正丙基氨基-3,8-二苯基-5-(4-甲基苯基)-6-甲基-5,8-二氢-4H-吡唑并[4',3':5,6]吡喃并[2,3-d]嘧啶-4(3H)-酮(Ⅲi)晶体结构。室内的杀菌和杀虫活性测试结果表明:目标化合物具有一定的杀菌活性,其中部分化合物对黄瓜灰霉菌(Botrytis cinereapers)在50 mg/L剂量下抑制率达到90%以上,显示了优异的杀菌活性;对水稻褐飞虱无明显的杀虫活性,但发现对粘虫具有较高的杀灭效果,大多数抑制率达到90%以上。

关键词: 氮杂Wittig反应, 吡唑并嘧啶, 吡喃并嘧啶, 生物活性

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

刘建超, 任青云, 贺红武. 吡唑并[4',3':5,6]吡喃并[2,3-d]嘧啶化合物的合成与生物活性[J]. 应用化学, 2017, 34(11): 1279-1286.

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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