苯基吡咯类杀菌剂的设计合成及三维-定量构效关系(3D-QSAR)研究

doi:10.6023/cjoc202102019

有机化学 ›› 2021, Vol. 41 ›› Issue (9): 3560-3570.DOI: 10.6023/cjoc202102019 上一篇下一篇

研究论文

苯基吡咯类杀菌剂的设计合成及三维-定量构效关系(3D-QSAR)研究

徐洪亮^a, 苏静^a, 王子时^a^,^*(), 侯晨忻^a, 吴鹏冲^a, 邢月^a, 李香帅^a, 朱晓磊^b, 路运才^a^,^*(), 徐利剑^a

a 黑龙江大学现代农业与生态环境学院哈尔滨 150080
b 华中师范大学化学学院武汉 430070

收稿日期:2021-03-24 修回日期:2021-06-14 发布日期:2021-07-12
通讯作者: 王子时, 路运才
基金资助:
国家重点研发计划(2017YFD0300405); 黑龙江省自然科学基金(LH2019C055); 黑龙江省自然科学基金(LH2019C056); 中国博士后科学基金(2019M651316); 黑龙江省博士后科学基金(LBH-Z18261); 黑龙江省省属高校基本科研(2020-KYYWF-1029); 黑龙江省省属高校基本科研(2020-KYYWF-1030); 黑龙江省省属高校基本科研(2020-KYYWF-1031); 黑龙江省省属高校基本科研(135409216); 黑龙江大学研究生创新科研重点(YJSCX2020-080HLJU)

Synthesis, Design and Three-Dimensional Quantitative Structure Activity Relationship (3D-QSAR) Research of Phenylpyrrole Fungicides

Hongliang Xu^a, Jing Su^a, Zishi Wang^a(), Chenxin Hou^a, Pengchong Wu^a, Yue Xing^a, Xiangshuai Li^a, Xiaolei Zhu^b, Yuncai Lu^a(), Lijian Xu^a

a College of Modern Agriculture and Ecological Environment, Heilongjiang University, Harbin 150080
b College of Chemistry, Central China Normal University, Wuhan 430079

Received:2021-03-24 Revised:2021-06-14 Published:2021-07-12
Contact: Zishi Wang, Yuncai Lu
Supported by:
National Key Research and Development Program of China(2017YFD0300405); Natural Science Foundation of Heilongjiang Province(LH2019C055); Natural Science Foundation of Heilongjiang Province(LH2019C056); Project Funded by China Postdoctoral Science Foundation(2019M651316); Heilongjiang Provincial Postdoctoral Science Foundation(LBH-Z18261); Department of Education of Heilongjiang Province(2020-KYYWF-1029); Department of Education of Heilongjiang Province(2020-KYYWF-1030); Department of Education of Heilongjiang Province(2020-KYYWF-1031); Department of Education of Heilongjiang Province(135409216); Heilongjiang University Graduate Innovative Research Fund Project(YJSCX2020-080HLJU)

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摘要/Abstract

为寻找新型吡咯类农药, 基于杀菌剂氟咯菌腈设计合成了21个苯基吡咯类化合物, 在吡咯环上引入甲基基团, 其目的是探究N位取代基对该类化合物活性的影响. 通过¹H NMR、FTIR、单晶X射线衍射、高分辨质谱、元素分析和熔点测定等对目标化合物结构进行了表征与确认, 并通过挥发法培养得到16个目标化合物的单晶结构. 5种病原菌抑菌活性测试结果显示: 在10 mg/L浓度条件下, 4-(2-氯苯基)-1H-吡咯-3-腈(4b), 4-(2-溴苯基)-1H-吡咯-3-腈(4c), 4-(2-(三氟甲基)苯基)-1H-吡咯-3-腈(4d), 4-(2-氯-3-氟苯基)-1H-吡咯-3-腈(4g), 4-(2,3-二氯苯基)-1H-吡咯-3-腈(4h)对4种病菌表现出较好甚至高于阳性对照的抑菌效果, 其中化合物4g在1 mg/L浓度条件下对3种病菌的抑制效果仍达到80%以上, 而氮位甲基取代的目标化合物对水稻纹枯病菌表现出专一的抑菌活性. 为了开发出更有效的抗水稻纹枯病菌化合物, 采用比较分子力场分析(CoMFA)方法对20个化合物的水稻纹枯病菌活性进行初步的三维-定量构效关系(3D-QSAR)研究, 建立了一个有效的CoMFA模型(q²=0.503, r²=0.974), 展现了良好的预测能力, 为后续该系列化合物的进一步优化提供了理论支持.

关键词: 吡咯类化合物, 杀菌剂, 氮位取代, 生物活性, 三维-定量构效关系(3D-QSAR)

Abstract In order to find new pyrrole pesticides, twenty one new pyrrole compounds based on the structure of fludioxonil were designed and synthesized. And a methyl group was introduced into the pyrrole ring to explore the effect of N-position substituent on the activity. All the structures of target products and intermediates were characterized and confirmed by ¹H NMR, FTIR, and single crystal X-ray diffraction, HRMS, elemental analysis and melting point determination. The single crystals of sixteen final products were obtained by volatilizing at room temperature. The antibacterial activity test results on the five pathogens show that under the concentration of 10 mg/L, 4-(2-chlorophenyl)-1H-pyrrole-3-carbonitrile (4b), 4-(2-bromopheny)-1H-pyrrole-3-carbonitrile (4c), 4-(2-(trifluoromethyl)phenyl)-1H-pyrrole-3-carbonitrile (4d), 4-(2-chloro-3-fluorophenyl)-1H-pyrrole-3-carbonitrile (4g), and 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carbonitrile (4h) showed even better or higher antibacterial effect on the four pathogens, the inhibitory effect of compound 4g on the three pathogens at a concentration of 1 mg/L also reached more than 80%. The target compounds substituted with methyl at the nitrogen position showed specific antibacterial activity against Rhizoctonia solani. In order to develop more effective antifungal compounds against Rhizoctonia solani, the three-dimensional quantitative structure activity relationship (3D-QSAR) study on the activity of 20 compounds against Rhizoctonia solani was preliminary conducted using comparative molecular force field analysis (CoMFA). A CoMFA model (q²=0.503, r²=0.974) was established, which showed good predictive ability, and also provided theoretical support for the further optimization of this series of compounds.

Key words: pyrrole compounds, fungicide, nitrogen substitution, biological activity, three-dimensional quantitative structure activity relationship (3D-QSAR)

引用此文

徐洪亮, 苏静, 王子时, 侯晨忻, 吴鹏冲, 邢月, 李香帅, 朱晓磊, 路运才, 徐利剑. 苯基吡咯类杀菌剂的设计合成及三维-定量构效关系(3D-QSAR)研究[J]. 有机化学, 2021, 41(9): 3560-3570.

Hongliang Xu, Jing Su, Zishi Wang, Chenxin Hou, Pengchong Wu, Yue Xing, Xiangshuai Li, Xiaolei Zhu, Yuncai Lu, Lijian Xu. Synthesis, Design and Three-Dimensional Quantitative Structure Activity Relationship (3D-QSAR) Research of Phenylpyrrole Fungicides[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3560-3570.

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Compd.	R¹	R²	R³
4a 4b 4c 4d 4e	F Cl Br CF₃ CH₃	H H H H H	H H H H H
4f	OCH₃	H	H
4g	Cl	F	H
4h	Cl	Cl	H
4i	CH₃	CH₃	H
4j	OCH₃	OCH₃	H
4k	F	CF₃	H
5a	F	H	CH₃
5b	Cl	H	CH₃
5c	Br	H	CH₃
5d	CF₃	H	CH₃
5e	CH₃	H	CH₃
5f	OCH₃	H	CH₃
5g	Cl	F	CH₃
5h	Cl	Cl	CH₃
5i	CH₃	CH₃	CH₃
5j	OCH₃	OCH₃	CH₃

Compd.	R¹	R²	R³
4a 4b 4c 4d 4e	F Cl Br CF₃ CH₃	H H H H H	H H H H H
4f	OCH₃	H	H
4g	Cl	F	H
4h	Cl	Cl	H
4i	CH₃	CH₃	H
4j	OCH₃	OCH₃	H
4k	F	CF₃	H
5a	F	H	CH₃
5b	Cl	H	CH₃
5c	Br	H	CH₃
5d	CF₃	H	CH₃
5e	CH₃	H	CH₃
5f	OCH₃	H	CH₃
5g	Cl	F	CH₃
5h	Cl	Cl	CH₃
5i	CH₃	CH₃	CH₃
5j	OCH₃	OCH₃	CH₃

Compd.	Fusarium moniliforme		Rhizoctonia solani		Pyricularia oryzae		Fusarium oxysporum f.sp. cucumerinum		Fusarium oxysporu
Compd.	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1
4a 4b 4c 4d 4e	80.01 94.42 63.88 93.42 39.22	28.78 71.71 44.22 77.63 4.71	83.75 93.50 94.24 93.42 83.93	54.76 80.51 66.82 79.6 63.6	56.71 50.00 90.71 87.85 74.26	7.46 41.3 45.71 46.42 6.61	6.94 7.04 20.39 6.08 20.25	4.16 2.11 2.63 4.72 9.49	84.61 91.55 91.42 84.86 92.14	53.84 77.27 74.28 71.71 41.42
4f	10.49	1.01	65.27	28.43	58.33	2.08	8.02	3.08	71.23	6.16
4g	89.04	84.24	93.58	80.12	91.42	65.00	27.84	7.59	91.78	83.56
4h	93.75	90.00	93.50	72.07	79.85	74.62	48.00	13.33	64.28	12.33
4i	72.65	36.47	56.90	23.49	77.61	38.80	19.33	5.33	88.66	52.66
4j	10.01	0.79	20.76	1.23	0.00	0.00	7.40	2.46	6.84	4.10
5a	13.28	0.03	75.55	57.4	0.00	0.00	9.02	5.55	28.87	2.81
5b	32.87	1.78	75.07	46.54	17.60	6.33	9.85	4.92	32.66	17.33
5c	32.66	3.99	47.65	8.93	21.64	8.20	12.83	3.37	29.87	16.23
5d	19.79	1.00	35.96	3.73	25.71	15.71	16.44	10.52	31.33	13.33
5e	18.95	1.42	59.85	12.80	21.21	6.06	12.00	6.00	15.78	5.92
5f	10.12	0.71	22.51	0.74	15.97	13.19	10.52	1.97	7.63	4.86
5g	17.33	5.33	53.24	20.77	13.23	2.20	7.33	4.66	16.66	9.33
5h	31.69	20.42	28.84	26.92	9.23	4.61	11.42	6.42	22.30	20.00
5i	15.04	1.91	59.81	25.72	36.42	7.85	25.32	12.33	38.46	7.69
5j	8.39	0.83	22.00	2.00	4.47	1.49	5.40	3.37	15.13	4.60
Fludioxonil^b	93.33	92.00	93.33	93.33	55.00	54.28	40.14	9.15	83.76	77.92

Compd.	Fusarium moniliforme		Rhizoctonia solani		Pyricularia oryzae		Fusarium oxysporum f.sp. cucumerinum		Fusarium oxysporu
Compd.	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1	10 mg•L^–1	1 mg•L^–1
4a 4b 4c 4d 4e	80.01 94.42 63.88 93.42 39.22	28.78 71.71 44.22 77.63 4.71	83.75 93.50 94.24 93.42 83.93	54.76 80.51 66.82 79.6 63.6	56.71 50.00 90.71 87.85 74.26	7.46 41.3 45.71 46.42 6.61	6.94 7.04 20.39 6.08 20.25	4.16 2.11 2.63 4.72 9.49	84.61 91.55 91.42 84.86 92.14	53.84 77.27 74.28 71.71 41.42
4f	10.49	1.01	65.27	28.43	58.33	2.08	8.02	3.08	71.23	6.16
4g	89.04	84.24	93.58	80.12	91.42	65.00	27.84	7.59	91.78	83.56
4h	93.75	90.00	93.50	72.07	79.85	74.62	48.00	13.33	64.28	12.33
4i	72.65	36.47	56.90	23.49	77.61	38.80	19.33	5.33	88.66	52.66
4j	10.01	0.79	20.76	1.23	0.00	0.00	7.40	2.46	6.84	4.10
5a	13.28	0.03	75.55	57.4	0.00	0.00	9.02	5.55	28.87	2.81
5b	32.87	1.78	75.07	46.54	17.60	6.33	9.85	4.92	32.66	17.33
5c	32.66	3.99	47.65	8.93	21.64	8.20	12.83	3.37	29.87	16.23
5d	19.79	1.00	35.96	3.73	25.71	15.71	16.44	10.52	31.33	13.33
5e	18.95	1.42	59.85	12.80	21.21	6.06	12.00	6.00	15.78	5.92
5f	10.12	0.71	22.51	0.74	15.97	13.19	10.52	1.97	7.63	4.86
5g	17.33	5.33	53.24	20.77	13.23	2.20	7.33	4.66	16.66	9.33
5h	31.69	20.42	28.84	26.92	9.23	4.61	11.42	6.42	22.30	20.00
5i	15.04	1.91	59.81	25.72	36.42	7.85	25.32	12.33	38.46	7.69
5j	8.39	0.83	22.00	2.00	4.47	1.49	5.40	3.37	15.13	4.60
Fludioxonil^b	93.33	92.00	93.33	93.33	55.00	54.28	40.14	9.15	83.76	77.92

q²^a	N^b	r²^c	S^d	F^e	Contribution%
q²^a	N^b	r²^c	S^d	F^e	Steric	Electrostatic
0.503	5	0.974	0.219	81.345	0.542	0.458

苯基吡咯类杀菌剂的设计合成及三维-定量构效关系(3D-QSAR)研究

Synthesis, Design and Three-Dimensional Quantitative Structure Activity Relationship (3D-QSAR) Research of Phenylpyrrole Fungicides

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Compd.	Experimental pEC₅₀	Predicted pEC₅₀	Residue
4a 4b 4c 4d 4e	2.408 3.581 2.774 2.882 2.801	2.504 3.504 2.691 3.101 2.818	–0.096 0.077 0.083 –0.219 –0.017
4f^*	1.705	1.641	0.064
4g	3.201	3.434	–0.233
4h	4.876	4.693	0.183
4i	1.487	1.582	–0.095
4j	0.789	0.766	0.023
4k	2.950	2.912	0.038
5a	1.814	1.932	–0.118
5b	2.062	2.028	0.034
5c^*	1.890	2.039	–0.149
5d	1.264	1.325	–0.061
5e^*	1.532	1.557	–0.025
5f	0.847	0.697	0.150
5g	1.994	2.111	–0.117
5i	1.397	1.294	0.103
5j	0.735	0.820	–0.085

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