取代吡唑-5-酰基杂环衍生物的合成、结构与生物活性

为了寻求新的含吡唑双杂环先导化合物. 用4-取代-1-甲基-3-乙基-5-吡唑甲酰氯与2-噻唑烷酮、2-噻唑硫酮、2-噁唑烷酮等含氮杂环反应得到了12个含吡唑环的双杂环化合物. 化合物结构用IR, ¹H NMR, MS和元素分析进行了表征. 并用X射线单晶衍射法测定了化合物3-(1-甲基-3-乙基-4-硝基-5-吡唑甲酰基)-噁唑烷-2-酮(3k)的晶体结构. 晶体为单斜晶系, P2₁/n (#14)空间群, a＝1.52175(3) nm, b＝0.52970(1) nm, c＝1.58185(3) nm, β＝104.893(4), V＝1.2323(4) nm³, Z＝4, D_c＝1.45 g/cm³, F(000)＝560.00, R₁＝0.064, wR₂＝0.193. 初步生物活性实验结果表明, 在25 mg/L浓度下, 3-(1-甲基-3-乙基-4-硝基-5-吡唑甲酰基)-噻唑烷-2-酮(3c), 3-(1-甲基-3-乙基-4-硝基-5-吡唑甲酰基)-噻唑烷-2-硫酮(3g)对水稻稻瘟病菌(Pyricularia oryzae)的抑制活性达到40%. 在500 mg/L浓度下, 3-(1-甲基-3-乙基-4-溴-5-吡唑甲酰基)-噻唑烷-2-酮(3d), 3-(1-甲基-3-乙基-4-溴-5-吡唑甲酰基)-噁唑烷-2-酮(3l)对稻黑尾叶蝉(Nephotettix cinc-ticeps)的抑制活性达到53.37%.

Synthesis, Structure and Biological Activities of Substi-tutedPyrazol-5-yl-carbonyl-heterocycles

In order to find new pyrazol-5-yl-carbonyl-heterocycles lead compounds, 12 pyrazolylheterocycles were synthesized from 3-ethyl-1-methyl-4-substitute-5- pyrazolecarboxylic acid chloride and nitrogen heterocyclic compounds such as 2-thiazolidone, 2-thiazolidinone, 2-oxazolidinone, etc. The structures of compounds obtained were confirmed by ¹H NMR, IR, MS spectra and elemental analysis. The crystal structure of 3-(3-ethyl-1-methyl-4-nitro-1H-pyrazol-5-yl-carbonyl)oxazolidin-2-one (3k) was deter-mined by X-ray diffraction analysis. 3k belongs to the monoclinic system with space group P2₁/n (#14) and cell dimensions: a＝1.52175(3) nm, b＝0.52970(1) nm, c＝1.58185(3) nm, β＝104.893(4), V＝1.2323(4) nm³, Z＝4, D_c＝1.45 g/cm³, F(000)＝560.00, R₁＝0.064, wR₂＝0.193. The results of biological tests indicated that, at 25 mg/L, 3-(3-ethyl-1-methyl-4-nitro-1H-pyrazole-5-carbonyl)thiazolidin-2-one (3c) and 3-(3-ethyl- 1-methyl-4-nitro-1H-pyrazole-5-carbonyl)-2-thiono-thiazolidine (3g) showed inhibitory activities of 40% against Pyricularia oryzae. At 500 mg/L, 3-(3-ethyl-1-methyl-4-bromo-1H-pyrazol-5-yl-carbonyl)thiazolidin-2-one (3d) and 3-(3-ethyl-1-methyl-4-bromo-1H-pyrazol-5-yl-carbonyl)oxazolidin-2-one (3l) showed in-hibitory activities of 53.37% against Nephotettix cincticeps.