含取代吡唑新型苯甲酰胺类化合物的合成及抗真菌活性研究

doi:10.6023/cjoc202108009

有机化学 ›› 2022, Vol. 42 ›› Issue (2): 607-618.DOI: 10.6023/cjoc202108009 上一篇下一篇

研究论文

含取代吡唑新型苯甲酰胺类化合物的合成及抗真菌活性研究

王伟^a, 武复冉^a, 马一丹^a, 徐丹^b^,^c^,^*(), 徐功^a^,^c^,^*()

a 西北农林科技大学植物保护学院陕西杨凌 712100
b 西北农林科技大学化学与药学院陕西杨凌 712100
c 西北农林科技大学旱区作物逆境生物学国家重点实验室陕西杨凌 712100

收稿日期:2021-08-07 修回日期:2021-09-18 发布日期:2022-02-24
通讯作者: 徐丹, 徐功
基金资助:
陕西省自然科学基础研究计划(2021JQ-157); 陕西省重点研发计划(2021NY-140); 中央高校基本科研业务费专项资金(2452019189); 中央高校基本科研业务费专项资金(2452018318)

Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit

Wei Wang^a, Furan Wu^a, Yidan Ma^a, Dan Xu^b^,^c(), Gong Xu^a^,^c()

a College of Plant Protection, Northwest A&F University, Yangling, Shaanxi 712100
b College of Chemistry & Pharmacy, Northwest A&F University, Yangling, Shaanxi 712100
c State Key Laboratory of Crop Stress Biology for Arid Areas, Northwest A&F University, Yangling, Shaanxi 712100

Received:2021-08-07 Revised:2021-09-18 Published:2022-02-24
Contact: Dan Xu, Gong Xu
Supported by:
Natural Science Basic Research Program of Shaanxi Province(2021JQ-157); Key Research and Development Program of Shaanxi Province(2021NY-140); Fundamental Research Funds for the Central Universities(2452019189); Fundamental Research Funds for the Central Universities(2452018318)

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摘要/Abstract

为了找寻新的杀菌剂, 运用活性片段拼接策略, 通过亚胺键将苯甲酰胺类衍生物和吡唑环连接起来, 设计并合成了一系列共计32个新型吡唑-5-基-苯甲酰胺类衍生物, 其结构经过NMR、HRMS分析确认, 并评估了它们的抗真菌活性. 生物测定数据显示, 大多数化合物表现出良好的抑制活性. 4-氯-N-(2-((1-甲基-3-(三氟甲基)-1H-吡唑-5-基)氨基)苯基)苯甲酰胺(14)对油菜菌核病菌和烟草赤星病菌表现出较好的体外活性, EC₅₀值分别为11.21和16.70 mg/L; 对于苹果腐烂病菌, 化合物14 (EC₅₀=11.67 mg/L)活性明显高于阳性对照药剂氟唑菌酰胺(EC₅₀=16.49 mg/L). 分子对接模拟表明, 化合物14通过氢键和p-π作用力与琥珀酸脱氢酶(SDH)的TYR 58和ARG 43相互作用, 这可以解释化合物14与靶蛋白作用的可能机制. 以上结果表明, 化合物14可能是潜在的SDH抑制剂, 并为进一步研究提供有价值的参考.

关键词: 吡唑, 苯甲酰胺, 抗真菌活性, 构效关系

To promote the discovery and development of new fungicides, a series of novel 1-methyl-pyrazol-5-yl-amino- phenyl-benzamide derivatives were designed and synthesized by active fragment splicing strategy, and the benzamide and pyrazole ring were connected together by imine bond. All of the target compounds were identified by NMR and high resolution mass spectrometry (HRMS), and evaluated for their antifungal activities. The bioassay data revealed that 4-chloro-N-(2-((1- methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)amino)phenyl)benzamide (14) exhibited an excellent in vitro activity against Sclerotinia sclerotiorum and Altenaria alternariae with EC₅₀ value of 11.21 and 16.70 mg/L, respectively. For Valsa mali, compound 14 (EC₅₀=11.67 mg/L) showed a significantly higher activity than the control of fluxapyroxad (EC₅₀=16.49 mg/L). The molecular docking simulation revealed that compound 14 interacted with TYR 58 and ARG 43 of the succinate dehydrogenase (SDH) through hydrogen bond and p-π interaction, which could explain the probable mechanism of the action between compound 14 and target protein. These results indicate that compound 14 may be a potential SDH inhibitor and provide a valuable reference for further research.

Key words: pyrazole, benzamide, antifungal activity, structure-activity relationships

引用此文

王伟, 武复冉, 马一丹, 徐丹, 徐功. 含取代吡唑新型苯甲酰胺类化合物的合成及抗真菌活性研究[J]. 有机化学, 2022, 42(2): 607-618.

Wei Wang, Furan Wu, Yidan Ma, Dan Xu, Gong Xu. Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 607-618.

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参考文献 21

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化合物	R¹	R²	油菜菌核病菌	苹果腐烂病菌	烟草赤星病菌	玉米弯孢病菌	葡萄灰霉病菌
8	CF₃	H	52.08±1.71	50.72±3.17	56.57±2.11	42.25±1.03	38.13±7.11
9	CF₃	2-F	81.22±3.54	64.31±6.88	73.68±0.86	45.42±1.42	58.52±2.44
10	CF₃	3-F	71.73±1.99	62.84±1.41	59.21±0.41	41.27±1.17	52.86±3.33
11	CF₃	4-F	67.96±5.25	60.68±4.58	65.45±1.04	41.28±2.74	47.90±4.21
12	CF₃	2-Cl	80.70±1.16	68.91 ±4.56	61.52±0.93	38.14±3.43	54.97±5.46
13	CF₃	3-Cl	87.99±1.96	82.38±1.30	64.47±0.66	47.21±0.53	68.82±3.08
14	CF₃	4-Cl	89.72±2.72	86.72±0.61	66.25±0.73	49.60±1.20	55.60±2.15
15	CF₃	2-CF₃	81.86±1.14	70.58±1.24	59.54±0.13	46.44±4.25	66.72±3.98
16	CF₃	3-CF₃	35.08±4.33	31.68±5.21	20.39±1.38	13.35±2.49	37.88±2.83
17	CF₃	4-CF₃	29.35±2.67	25.63±6.12	17.76±0.57	25.88±1.08	38.67±6.48
18	CF₃	2-CH₃	61.85±3.47	54.59±5.01	48.03±0.28	36.23±4.24	48.50±1.02
19	CF₃	3-CH₃	35.24±4.23	28.28±3.35	21.70±0.91	23.53±3.60	22.73±6.60
20	CF₃	4-CH₃	82.80±1.40	89.95±0.63	58.22±1.45	50.38±1.98	55.41±2.72
21	CF₃	2-OCH₃	65.30±2.03	54.53±4.30	51.98±0.75	24.39±1.32	36.47±3.42
22	CF₃	3-OCH₃	64.64±3.29	60.27±5.18	54.28±0.59	39.25±2.33	33.06±1.46
23	CF₃	4-OCH₃	75.43±1.04	79.72±1.55	55.19±1.53	47.05±3.34	50.42±3.87
24	CHF₂	H	62.64±3.40	32.89±5.39	35.85±0.75	47.75±3.03	33.47±4.14
25	CHF₂	2-F	41.09±2.11	40.10±7.63	48.04±1.57	37.02±3.65	33.66±2.53
26	CHF₂	3-F	60.73±7.33	36.71±6.59	39.15±1.27	25.37±1.05	51.45±8.28
27	CHF₂	4-F	44.79±0.80	44.55±3.40	38.82±1.45	24.77±0.65	48.46±3.99
28	CHF₂	2-Cl	55.77±1.94	56.96±4.78	50.98±0.48	35.40±1.87	72.36±3.68
29	CHF₂	3-Cl	84.94±0.83	72.29±2.17	58.22±0.41	45.61±0.45	70.42±6.84
30	CHF₂	4-Cl	83.42±0.36	73.18±2.35	52.31±1.06	47.56±0.67	51.88±4.87
31	CHF₂	2-CF₃	49.10±0.68	46.60±5.94	41.11±0.52	32.65±0.33	32.28±6.58
32	CHF₂	3-CF₃	80.02±1.48	66.90±3.16	56.58±0.14	33.15±3.38	73.25±3.92
33	CHF₂	4-CF₃	30.49±4.19	31.32±5.49	25.00±2.40	14.43±1.23	63.35±7.24
34	CHF₂	2-CH₃	43.27±5.48	42.28±2.61	41.77±1.17	32.05±0.54	54.95±7.68
35	CHF₂	3-CH₃	44.09±2.12	59.53±2.66	46.71±0.91	27.71±1.23	25.06±0.81
36	CHF₂	4-CH₃	70.16±1.97	55.18±2.34	44.74±0.60	43.86±2.85	28.40±4.13
37	CHF₂	2-OCH₃	63.44±1.42	58.43±1.58	56.25±0.73	37.29±2.16	36.51±3.80
38	CHF₂	3-OCH₃	63.48±1.50	38.35±3.45	42.76±0.60	44.24±3.42	24.84±6.94
39	CHF₂	4-OCH₃	46.79±4.29	44.15±3.47	45.73±1.55	36.98±3.94	25.32±4.76
5IIc^c	CHF₂	3-CH₃	100	95.00±0.41	67.62±2.24	52.42±1.34	89.33±1.92
氟唑菌酰胺^b			100	81.30±2.70	95.07±0.65	100	63.16±1.24

化合物	R¹	R²	油菜菌核病菌	苹果腐烂病菌	烟草赤星病菌	玉米弯孢病菌	葡萄灰霉病菌
8	CF₃	H	52.08±1.71	50.72±3.17	56.57±2.11	42.25±1.03	38.13±7.11
9	CF₃	2-F	81.22±3.54	64.31±6.88	73.68±0.86	45.42±1.42	58.52±2.44
10	CF₃	3-F	71.73±1.99	62.84±1.41	59.21±0.41	41.27±1.17	52.86±3.33
11	CF₃	4-F	67.96±5.25	60.68±4.58	65.45±1.04	41.28±2.74	47.90±4.21
12	CF₃	2-Cl	80.70±1.16	68.91 ±4.56	61.52±0.93	38.14±3.43	54.97±5.46
13	CF₃	3-Cl	87.99±1.96	82.38±1.30	64.47±0.66	47.21±0.53	68.82±3.08
14	CF₃	4-Cl	89.72±2.72	86.72±0.61	66.25±0.73	49.60±1.20	55.60±2.15
15	CF₃	2-CF₃	81.86±1.14	70.58±1.24	59.54±0.13	46.44±4.25	66.72±3.98
16	CF₃	3-CF₃	35.08±4.33	31.68±5.21	20.39±1.38	13.35±2.49	37.88±2.83
17	CF₃	4-CF₃	29.35±2.67	25.63±6.12	17.76±0.57	25.88±1.08	38.67±6.48
18	CF₃	2-CH₃	61.85±3.47	54.59±5.01	48.03±0.28	36.23±4.24	48.50±1.02
19	CF₃	3-CH₃	35.24±4.23	28.28±3.35	21.70±0.91	23.53±3.60	22.73±6.60
20	CF₃	4-CH₃	82.80±1.40	89.95±0.63	58.22±1.45	50.38±1.98	55.41±2.72
21	CF₃	2-OCH₃	65.30±2.03	54.53±4.30	51.98±0.75	24.39±1.32	36.47±3.42
22	CF₃	3-OCH₃	64.64±3.29	60.27±5.18	54.28±0.59	39.25±2.33	33.06±1.46
23	CF₃	4-OCH₃	75.43±1.04	79.72±1.55	55.19±1.53	47.05±3.34	50.42±3.87
24	CHF₂	H	62.64±3.40	32.89±5.39	35.85±0.75	47.75±3.03	33.47±4.14
25	CHF₂	2-F	41.09±2.11	40.10±7.63	48.04±1.57	37.02±3.65	33.66±2.53
26	CHF₂	3-F	60.73±7.33	36.71±6.59	39.15±1.27	25.37±1.05	51.45±8.28
27	CHF₂	4-F	44.79±0.80	44.55±3.40	38.82±1.45	24.77±0.65	48.46±3.99
28	CHF₂	2-Cl	55.77±1.94	56.96±4.78	50.98±0.48	35.40±1.87	72.36±3.68
29	CHF₂	3-Cl	84.94±0.83	72.29±2.17	58.22±0.41	45.61±0.45	70.42±6.84
30	CHF₂	4-Cl	83.42±0.36	73.18±2.35	52.31±1.06	47.56±0.67	51.88±4.87
31	CHF₂	2-CF₃	49.10±0.68	46.60±5.94	41.11±0.52	32.65±0.33	32.28±6.58
32	CHF₂	3-CF₃	80.02±1.48	66.90±3.16	56.58±0.14	33.15±3.38	73.25±3.92
33	CHF₂	4-CF₃	30.49±4.19	31.32±5.49	25.00±2.40	14.43±1.23	63.35±7.24
34	CHF₂	2-CH₃	43.27±5.48	42.28±2.61	41.77±1.17	32.05±0.54	54.95±7.68
35	CHF₂	3-CH₃	44.09±2.12	59.53±2.66	46.71±0.91	27.71±1.23	25.06±0.81
36	CHF₂	4-CH₃	70.16±1.97	55.18±2.34	44.74±0.60	43.86±2.85	28.40±4.13
37	CHF₂	2-OCH₃	63.44±1.42	58.43±1.58	56.25±0.73	37.29±2.16	36.51±3.80
38	CHF₂	3-OCH₃	63.48±1.50	38.35±3.45	42.76±0.60	44.24±3.42	24.84±6.94
39	CHF₂	4-OCH₃	46.79±4.29	44.15±3.47	45.73±1.55	36.98±3.94	25.32±4.76
5IIc^c	CHF₂	3-CH₃	100	95.00±0.41	67.62±2.24	52.42±1.34	89.33±1.92
氟唑菌酰胺^b			100	81.30±2.70	95.07±0.65	100	63.16±1.24

真菌	化合物	R¹	R²	EC₅₀/(mg•L^–1)	95%置信区间	毒力回归方程	R²
油菜菌核病菌	9	CF₃	2-F	18.90	11.96~37.56	y=–1.684+1.319x	0.931
	10	CF₃	3-F	21.58	16.37~30.82	y=–1.289+0.966x	0.932
	11	CF₃	4-F	30.11	23.06~42.76	y=–1.687+1.141x	0.948
	12	CF₃	2-Cl	20.07	12.49~42.19	y=–1.772+1.360x	0.929
	13	CF₃	3-Cl	15.09	9.36~28.97	y=–1.718+1.457x	0.925
	14	CF₃	4-Cl	11.21	7.32~18.12	y=–1.613+1.537x	0.941
	15	CF₃	2-CF₃	14.74	9.43~26.83	y=–1.360+1.164x	0.927
	20	CF₃	4-CH₃	15.99	9.72~32.97	y=–1.492+1.240x	0.920
	23	CF₃	4-OCH₃	21.98	13.64~47.94	y=–1.595+1.188x	0.932
	29	CHF₂	3-Cl	17.96	11.24~35.80	y=–1.859+1.482x	0.931
	30	CHF₂	4-Cl	18.73	11.85~37.00	y=–1.864+1.464x	0.935
	32	CHF₂	3-CF₃	19.49	11.86~43.08	y=–1.639+1.271x	0.921
	36	CHF₂	4-CH₃	23.76	18.25~33.32	y=–1.451+1.055x	0.957
	氟唑菌酰胺^a			0.55	0.20~0.98	y=0.253+0.974x	0.930
苹果腐烂病菌	9	CF₃	2-F	28.46	19.88~47.86	y=–1.150+0.91x	0.926
	10	CF₃	3-F	27.26	18.52~48.47	y=–1.025+0.714x	0.915
	11	CF₃	4-F	28.84	19.18~53.99	y=–0.999+0.684x	0.958
	12	CF₃	2-Cl	20.86	14.98~32.71	y=–1.028+0.779x	0.918
	13	CF₃	3-Cl	11.17	6.91~19.58	y=–1.249+1.191x	0.918
	14	CF₃	4-Cl	11.67	7.51~19.69	y=–1.138+1.067x	0.933
	15	CF₃	2-CF₃	19.23	14.12~28.78	y=–1.059+0.829x	0.928
	20	CF₃	4-CH₃	16.14	9.92~32.04	y=–1.957+1.620x	0.922
	23	CHF₂	4-OCH₃	16.23	10.87~28.38	y=–1.423+1.175x	0.939
	29	CHF₂	3-Cl	16.01	11.98~22.91	y=–1.019+0.846x	0.940
	30	CHF₂	4-Cl	18.86	14.56~25.99	y=–1.277+1.001x	0.946
	32	CHF₂	3-CF₃	20.83	16.63~27.36	y=–1.599+1.212x	0.961
	36	CHF₂	4-CH₃	46.72	31.92~82.28	y=–1.528+0.916x	0.974
	氟唑菌酰胺^a			16.49	11.81~27.49	y=–1.112+0.914x	0.984
烟草赤星病菌	9	CF₃	2-F	17.19	4.89~28.20	y=–1.627+1.317x	0.990
	10	CF₃	3-F	39.89	26.67~73.75	y=–1.274+0.796x	0.944
	11	CF₃	4-F	26.60	15.58~71.12	y=–1.333+0.936x	0.906
	12	CF₃	2-Cl	31.06	21.76~51.93	y=–1.234+0.827x	0.934
	13	CF₃	3-Cl	25.89	19.82~36.60	y=–1.514+1.071x	0.979
	14	CF₃	4-Cl	16.70	13.64~20.91	y=–1.162+0.858x	0.959
	15	CF₃	2-CF₃	32.58	25.23~70.83	y=–1.142+0.755x	0.963
	20	CF₃	4-CH₃	34.97	3.45~62.57	y=–1.568+1.016x	0.946
	23	CF₃	4-OCH₃	33.02	21.90~62.36	y=–1.088+0.716x	0.938
	29	CHF₂	3-Cl	37.16	24.82~69.89	y=–1.383+0.881x	0.948
	30	CHF₂	4-Cl	50.71	31.21~112.50	y=–0.984+0.577x	0.993
	32	CHF₂	3-CF₃	46.83	30.65~90.41	y=–1.344+0.804x	0.922
	氟唑菌酰胺^a			0.68	0.23~1.27	y=0.125+0.773x	0.941

真菌	化合物	R¹	R²	EC₅₀/(mg•L^–1)	95%置信区间	毒力回归方程	R²
油菜菌核病菌	9	CF₃	2-F	18.90	11.96~37.56	y=–1.684+1.319x	0.931
	10	CF₃	3-F	21.58	16.37~30.82	y=–1.289+0.966x	0.932
	11	CF₃	4-F	30.11	23.06~42.76	y=–1.687+1.141x	0.948
	12	CF₃	2-Cl	20.07	12.49~42.19	y=–1.772+1.360x	0.929
	13	CF₃	3-Cl	15.09	9.36~28.97	y=–1.718+1.457x	0.925
	14	CF₃	4-Cl	11.21	7.32~18.12	y=–1.613+1.537x	0.941
	15	CF₃	2-CF₃	14.74	9.43~26.83	y=–1.360+1.164x	0.927
	20	CF₃	4-CH₃	15.99	9.72~32.97	y=–1.492+1.240x	0.920
	23	CF₃	4-OCH₃	21.98	13.64~47.94	y=–1.595+1.188x	0.932
	29	CHF₂	3-Cl	17.96	11.24~35.80	y=–1.859+1.482x	0.931
	30	CHF₂	4-Cl	18.73	11.85~37.00	y=–1.864+1.464x	0.935
	32	CHF₂	3-CF₃	19.49	11.86~43.08	y=–1.639+1.271x	0.921
	36	CHF₂	4-CH₃	23.76	18.25~33.32	y=–1.451+1.055x	0.957
	氟唑菌酰胺^a			0.55	0.20~0.98	y=0.253+0.974x	0.930
苹果腐烂病菌	9	CF₃	2-F	28.46	19.88~47.86	y=–1.150+0.91x	0.926
	10	CF₃	3-F	27.26	18.52~48.47	y=–1.025+0.714x	0.915
	11	CF₃	4-F	28.84	19.18~53.99	y=–0.999+0.684x	0.958
	12	CF₃	2-Cl	20.86	14.98~32.71	y=–1.028+0.779x	0.918
	13	CF₃	3-Cl	11.17	6.91~19.58	y=–1.249+1.191x	0.918
	14	CF₃	4-Cl	11.67	7.51~19.69	y=–1.138+1.067x	0.933
	15	CF₃	2-CF₃	19.23	14.12~28.78	y=–1.059+0.829x	0.928
	20	CF₃	4-CH₃	16.14	9.92~32.04	y=–1.957+1.620x	0.922
	23	CHF₂	4-OCH₃	16.23	10.87~28.38	y=–1.423+1.175x	0.939
	29	CHF₂	3-Cl	16.01	11.98~22.91	y=–1.019+0.846x	0.940
	30	CHF₂	4-Cl	18.86	14.56~25.99	y=–1.277+1.001x	0.946
	32	CHF₂	3-CF₃	20.83	16.63~27.36	y=–1.599+1.212x	0.961
	36	CHF₂	4-CH₃	46.72	31.92~82.28	y=–1.528+0.916x	0.974
	氟唑菌酰胺^a			16.49	11.81~27.49	y=–1.112+0.914x	0.984
烟草赤星病菌	9	CF₃	2-F	17.19	4.89~28.20	y=–1.627+1.317x	0.990
	10	CF₃	3-F	39.89	26.67~73.75	y=–1.274+0.796x	0.944
	11	CF₃	4-F	26.60	15.58~71.12	y=–1.333+0.936x	0.906
	12	CF₃	2-Cl	31.06	21.76~51.93	y=–1.234+0.827x	0.934
	13	CF₃	3-Cl	25.89	19.82~36.60	y=–1.514+1.071x	0.979
	14	CF₃	4-Cl	16.70	13.64~20.91	y=–1.162+0.858x	0.959
	15	CF₃	2-CF₃	32.58	25.23~70.83	y=–1.142+0.755x	0.963
	20	CF₃	4-CH₃	34.97	3.45~62.57	y=–1.568+1.016x	0.946
	23	CF₃	4-OCH₃	33.02	21.90~62.36	y=–1.088+0.716x	0.938
	29	CHF₂	3-Cl	37.16	24.82~69.89	y=–1.383+0.881x	0.948
	30	CHF₂	4-Cl	50.71	31.21~112.50	y=–0.984+0.577x	0.993
	32	CHF₂	3-CF₃	46.83	30.65~90.41	y=–1.344+0.804x	0.922
	氟唑菌酰胺^a			0.68	0.23~1.27	y=0.125+0.773x	0.941

含取代吡唑新型苯甲酰胺类化合物的合成及抗真菌活性研究

Study on Synthesis and Antifungal Activity of Novel Benzamides Containing Substituted Pyrazole Unit

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