Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety

doi:10.6023/cjoc202008006

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 708-718.DOI: 10.6023/cjoc202008006 Previous Articles Next Articles

Article

含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究

贺军¹, 唐雪梅¹, 周清¹, 彭峰¹, 刘婷婷¹, 柳立伟¹, 贺鸣¹, 谢承卫¹, 薛伟¹^,^*()

1 贵州大学精细化工研究开发中心绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与生物工程重点实验室贵阳 550025

收稿日期:2020-08-07 修回日期:2020-09-04 发布日期:2020-10-12
通讯作者: 薛伟
作者简介:
* Corresponding author. E-mail: wxue@gzu.edu.cn
基金资助:
国家自然科学基金(21867003); 贵州省自然科学基金(20192452); 贵州省自然科学基金(20191105); 贵州省自然科学基金(20171028)

Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety

Jun He¹, Xuemei Tang¹, Qing Zhou¹, Feng Peng¹, Tingting Liu¹, Liwei Liu¹, Ming He¹, Chengwei Xie¹, Wei Xue¹^,^*()

1 Laboratory of Green Pesticide and Bioengineering of Ministry of Education, State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2020-08-07 Revised:2020-09-04 Published:2020-10-12
Contact: Wei Xue
Supported by:
the National Natural Science Foundation of China(21867003); the Natural Science Foundation of Guizhou Province(20192452); the Natural Science Foundation of Guizhou Province(20191105); the Natural Science Foundation of Guizhou Province(20171028)

1. cjoc202008006辅助材料.pdf(3517KB)

Abstract

A series of myricetin derivatives containing quinazoline thioether moiety were designed and synthesized using myricetrin as the starting material through active splicing strategy. All target compounds were characterized by ¹H NMR, ¹³C NMR, ¹⁹F NMR and HRMS. Their biological activities were evaluated. The results of biological activities showed that these compounds exhibited certain inhibitory activities against X. oryzae, X. citri and R. solanacearum. Among them, 3-(3-((6-bro- moquinazolin-4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₅) displayed appreciable inhibitory effect against X. oryzae with a half maximal effective concentration (EC₅₀) values of 13.9 μg/mL, which was better than those of the control drugs of bismerthiazol (88.9 μg/mL) and thiodiazole-copper (68.1 μg/mL). The EC₅₀ values of 3-(4- ((6-chloroquinazolin-4-yl)thio)butoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₃), 3-(3-((6-chloro- quinazolin-4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₄), 3-(3-((6-chloroquinazolin- 4-yl)thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₅) and 3-(3-((6-fluoroquinazolin-4-yl)- thio)propoxy)-5,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (A₁₆) against Ralstonia solanacearum were 1.1, 14.0, 11.9 and 7.5 μg/mL, respectively, which were superior to the control drugs of bismerthiazol (38.5 μg/mL) and thio-diazole-copper (184.8 μg/mL). The results of in vivo experiments showed that compound A₁₅ has good curative and protective activities against X. oryzae. The possible antibacterial mechanisms of target compound A₃ against R. solanacearum and A₁₅ against X. oryzae were preliminarily discussed base on scanning electron microscope analyses.

Key words: myricetin derivative, quinazoline thioether, biological activity, in vivo experiment, scanning electron microscope

Cite this article

Jun He, Xuemei Tang, Qing Zhou, Feng Peng, Tingting Liu, Liwei Liu, Ming He, Chengwei Xie, Wei Xue. Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 708-718.

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Compd.	R	n	X. oryzae				R. solanacearum
Compd.	R	n	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
A₁	6-Me	4	22.2±8.1	20.0±4.2	15.6±2.9	14.9±1.3	—	—
A₂	8-Me	4	32.7±0.1	16.6±3.5	10.1±5.3	6.7±2.9	21.5±1.6	13.3±0.5
A₃	Cl	4	59.9±4.6	27.3±0.3	11.3±2.7	—	88.4±5.5	83.8±4.4
A₄	6-Br	4	64.2±5.2	42.0±0.6	—	—	86.8±3.5	55.5±4.5
A₅	6-F	4	42.2±6.4	35.5±1.1	11.2±3.8	9.6±1.9	66.9±3.8	44.1±2.4
A₆	7-Cl	4	30.9±4.9	28.4±5.2	8.5±3.4	6.7±1.0	65.8±3.4	57.1±3.9
A₇	6-I	4	28.7±3.9	26.5±2.6	—	—	80.7±2.9	63.0±3.5
A₈	6-Cl-8-Me	4	42.6±3.4	36.6±0.9	30.0 ± 5.0	23.3±1.7	70.4±1.3	77.3±6.8
A₉	7-F	4	50.4±2.0	30.1±1.3	16.6±0.8	22.2±3.4	70.8±4.0	59.1±3.9
A₁₀	6,7-(OMe)₂	4	41.4±2.4	28.1±2.0	8.8±2.2	5.3±1.6	40.7±6.1	27.1±7.0
A₁₁	7,8-Me₂	4	40.4±4.4	34.2±5.5	—	—	22.2±5.4	16.9±6.5
A₁₂	6-Me	3	23.7±4.5	23.4±1.7	12.5±1.2	12.7±2.3	12.1±5.4	—
A₁₃	8-Me	3	26.8±2.8	23.2±7.4	11.5±2.9	4.4±1.8	8.7±4.3	—
A₁₄	6-Cl	3	44.6±2.5	29.8±2.9	33.1±2.2	13.3±2.2	77.6±1.3	71.3±3.8
A₁₅	6-Br	3	86.1±5.1	71.4±4.5	58.0±2.3	12.1±1.1	99.1±3.0	76.2±3.6
A₁₆	6-F	3	44.9±3.2	40.6±4.7	—	—	73.1±2.7	66.0±5.2
A₁₇	7-Cl	3	31.2±2.8	28.4±3.2	19.3±1.2	15.2±0.6	19.7±3.5	12.7±1.6
A₁₈	6-I	3	62.8±3.8	39.9±5.6	56.2±3.4	28.3±0.9	35.1±5.2	19.1±1.2
A₁₉	6-Cl-8-Me	3	42.7±3.4	36.0±7.4	21.1±5.0	19.0±2.2	50.8±1.6	42.8±0.7
A₂₀	7-F	3	41.4±4.4	29.2±0.8	23.8±1.6	10.6±4.2	63.3±8.7	39.1±4.5
A₂₁	6,7-(OMe)₂	3	34.1±2.8	24.5±0.8	12.1±3.0	—	12.1±4.1	6.6±2.9
A₂₂	7,8-Me₂	3	58.0±2.3	47.7±0.4	18.3±5.3	11.6±6.9	38.5±2.9	33.4±6.7
中间体1	—	—	35.5±1.6	18.3±1.9	18.9±4.0	9.3±2.8	40.8±2.0	14.0±1.3
杨梅素	—	—	30.3±5.3	10.6±0.5	11.0±3.5	—	9.3±4.5	5.2±3.0
杨梅苷	—	—	10.9±3.9	8.9±5.1	—	—	20.9±2.0	7.7±4.8
叶枯唑^b	—	—	55.1±1.82	39.0±1.8	51.4±2.0	19.2±2.0	59.5±5.7	51.7±0.2
噻菌铜^b	—	—	62.2±4.8	36.1±4.4	63.3±0.6	18.5±6.0	38.4±3.8	20.9±1.6

Compd.	R	n	X. oryzae				R. solanacearum
Compd.	R	n	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
A₁	6-Me	4	22.2±8.1	20.0±4.2	15.6±2.9	14.9±1.3	—	—
A₂	8-Me	4	32.7±0.1	16.6±3.5	10.1±5.3	6.7±2.9	21.5±1.6	13.3±0.5
A₃	Cl	4	59.9±4.6	27.3±0.3	11.3±2.7	—	88.4±5.5	83.8±4.4
A₄	6-Br	4	64.2±5.2	42.0±0.6	—	—	86.8±3.5	55.5±4.5
A₅	6-F	4	42.2±6.4	35.5±1.1	11.2±3.8	9.6±1.9	66.9±3.8	44.1±2.4
A₆	7-Cl	4	30.9±4.9	28.4±5.2	8.5±3.4	6.7±1.0	65.8±3.4	57.1±3.9
A₇	6-I	4	28.7±3.9	26.5±2.6	—	—	80.7±2.9	63.0±3.5
A₈	6-Cl-8-Me	4	42.6±3.4	36.6±0.9	30.0 ± 5.0	23.3±1.7	70.4±1.3	77.3±6.8
A₉	7-F	4	50.4±2.0	30.1±1.3	16.6±0.8	22.2±3.4	70.8±4.0	59.1±3.9
A₁₀	6,7-(OMe)₂	4	41.4±2.4	28.1±2.0	8.8±2.2	5.3±1.6	40.7±6.1	27.1±7.0
A₁₁	7,8-Me₂	4	40.4±4.4	34.2±5.5	—	—	22.2±5.4	16.9±6.5
A₁₂	6-Me	3	23.7±4.5	23.4±1.7	12.5±1.2	12.7±2.3	12.1±5.4	—
A₁₃	8-Me	3	26.8±2.8	23.2±7.4	11.5±2.9	4.4±1.8	8.7±4.3	—
A₁₄	6-Cl	3	44.6±2.5	29.8±2.9	33.1±2.2	13.3±2.2	77.6±1.3	71.3±3.8
A₁₅	6-Br	3	86.1±5.1	71.4±4.5	58.0±2.3	12.1±1.1	99.1±3.0	76.2±3.6
A₁₆	6-F	3	44.9±3.2	40.6±4.7	—	—	73.1±2.7	66.0±5.2
A₁₇	7-Cl	3	31.2±2.8	28.4±3.2	19.3±1.2	15.2±0.6	19.7±3.5	12.7±1.6
A₁₈	6-I	3	62.8±3.8	39.9±5.6	56.2±3.4	28.3±0.9	35.1±5.2	19.1±1.2
A₁₉	6-Cl-8-Me	3	42.7±3.4	36.0±7.4	21.1±5.0	19.0±2.2	50.8±1.6	42.8±0.7
A₂₀	7-F	3	41.4±4.4	29.2±0.8	23.8±1.6	10.6±4.2	63.3±8.7	39.1±4.5
A₂₁	6,7-(OMe)₂	3	34.1±2.8	24.5±0.8	12.1±3.0	—	12.1±4.1	6.6±2.9
A₂₂	7,8-Me₂	3	58.0±2.3	47.7±0.4	18.3±5.3	11.6±6.9	38.5±2.9	33.4±6.7
中间体1	—	—	35.5±1.6	18.3±1.9	18.9±4.0	9.3±2.8	40.8±2.0	14.0±1.3
杨梅素	—	—	30.3±5.3	10.6±0.5	11.0±3.5	—	9.3±4.5	5.2±3.0
杨梅苷	—	—	10.9±3.9	8.9±5.1	—	—	20.9±2.0	7.7±4.8
叶枯唑^b	—	—	55.1±1.82	39.0±1.8	51.4±2.0	19.2±2.0	59.5±5.7	51.7±0.2
噻菌铜^b	—	—	62.2±4.8	36.1±4.4	63.3±0.6	18.5±6.0	38.4±3.8	20.9±1.6

Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
A₄	4	6-Br	y=1.8096x+1.6782	0.9627	68.5
A₁₅	3	6-Br	y=1.1947x+3.6346	0.9934	13.9
A₁₈	3	6-I	y=1.3339x+2.4922	0.9715	75.9
噻菌铜^a	—	—	y=1.8570x+1.5964	0.9910	68.1
叶枯唑^a	—	—	y=1.2079x+2.6426	0.9844	88.9

Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
A₄	4	6-Br	y=1.8096x+1.6782	0.9627	68.5
A₁₅	3	6-Br	y=1.1947x+3.6346	0.9934	13.9
A₁₈	3	6-I	y=1.3339x+2.4922	0.9715	75.9
噻菌铜^a	—	—	y=1.8570x+1.5964	0.9910	68.1
叶枯唑^a	—	—	y=1.2079x+2.6426	0.9844	88.9

Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
A₃	4	6-Cl	y=0.593x+4.9827	0.9921	1.1
A₄	4	6-Br	y=1.8966x+2.1798	0.9632	30.7
A₅	4	6-F	y=0.8597x+3.5656	0.9585	46.6
A₆	4	7-Cl	y=0.5752x+4.2419	0.9636	20.1
A₇	4	6-I	y=1.4886x+2.9695	0.9507	23.1
A₈	4	6-Cl-8-Me	y=1.4015x+3.064	0.9633	24.1
A₉	4	7-F	y=1.3577x+2.8057	0.9934	41.3
A₁₄	3	6-Cl	y=0.9359x+3.9275	0.9617	14.0
A₁₅	3	6-Br	y=1.7487x+3.0242	0.9766	11.9
A₁₆	3	6-F	y=0.8035x+4.2979	0.9904	7.5
A₂₀	3	6-Cl-8-Me	y=0.538x+3.9015	0.9582	110.1

含喹唑啉硫醚的杨梅素衍生物的设计、合成及生物活性研究

Design, Synthesis and Biological Activities of Myricetin Derivatives Containing Quinazoline Thioether Moiety

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Compd.	n	R	Toxic regression equation	r	EC₅₀/(μg?mL^–1)
噻菌铜^a	—	—	y=0.6931x+3.4289	0.9773	184.8
叶枯唑^a	—	—	y=0.8701x+4.0372	0.9753	38.5

Treatment	Morbidity/ %	Disease index/ %	Control efficiency/ %
A₁₅	100	44.1	49.4
叶枯唑^a	100	47.6	45.3
噻菌铜^a	100	56.8	34.8
CK^b	100	87.0	—

Treatment	Morbidity/ %	Disease index/ %	Control efficiency/ %
A₁₅	100	45.9	47.2
叶枯唑^a	100	45.5	47.7
噻菌铜^a	100	56.5	35.1
CK^b	100	87.0	—

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