Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination

doi:10.6023/cjoc202307014

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 309-315.DOI: 10.6023/cjoc202307014 Previous Articles Next Articles

吗啉磺酰胺化合物的设计、合成及其抑制大豆萌芽活性的研究

黄志友^a, 杨平^a, 何波^b^,^*(), 欧文霞^a, 袁思雨^a

a 邵阳学院农林生态学院湖南邵阳 422000
b 南京农业大学植物保护学院农作物生物灾害综合治理教育部重点实验室南京 210095

收稿日期:2023-07-15 修回日期:2023-08-19 发布日期:2023-09-28
基金资助:
湖南省自然科学基金青年(2021JJ40515); 湖南省教育厅优秀青年(21B0677)

Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination

Zhiyou Huang^a, Ping Yang^a, Bo He^b(), Wenxia Ou^a, Siyu Yuan^a

a College of Agriculture Forestry Ecology, Shaoyang University, Shaoyang 422000
b Key Laboratory of Integrated Management of Crop Disease and Pests, Ministry of Education, College of Plant Protection, Nanjing Agricultural University, Nanjing 210095

Received:2023-07-15 Revised:2023-08-19 Published:2023-09-28
Contact: *E-mail: 1046081380@qq.com
Supported by:
Natural Science Foundation of Hunan Province Youth Project(2021JJ40515); Scientific Research Fund of Hunan Provincial Education Department(21B0677)

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Abstract

In order to obtain novel abscisic acid analogues, morpholine-sulfonamide compound was designed under the principle of active substructure combination. 14 target compounds were obtained through aromatic nucleophilic substitution (S_NAr) when fluoride nitrobenzene and morpholine-4-sulfonamide were used as starting materials. The approach represents simple operation and broad substrate scope. Additionally, the soybean seed germination was inhibited overwhelmingly when treated with compounds 4a~4d, 4k, 4m and 4n at 50 μmol/L. Furthermore, the inhibition activity of compounds 4a~4d, 4k, 4m and 4n was higher than 95% at 25 μmol/L. Finally, the activity of 4m and 4n was much higher than that of ABA and lead compound (PM4) at 15 μmol/L. Moreover, the molecular docking study revealed that 4m and 4n could bind abscisic acid receptor strongly than ABA and PM4. These results are benefit to discovering novel ABA analogues.

Key words: ABA functional analogue, morpholine sulfonamide, inhibition germination, aromatic nucleophilic substitution

Cite this article

Zhiyou Huang, Ping Yang, Bo He, Wenxia Ou, Siyu Yuan. Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 309-315.

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Entry	T/℃	n(5)∶n(6a)	t/h	Base	Solvent	Yield/%
1	80	1∶1	4	K₃PO₄	DMF	18
2	80	1∶1	8	K₃PO₄	DMF	33
3	80	1∶1	12	K₃PO₄	DMF	40
4	80	1∶1	14	K₃PO₄	DMF	40
5	85	1∶1	12	K₃PO₄	DMF	47
6	90	1∶1	12	K₃PO₄	DMF	53
7	100	1∶1	12	K₃PO₄	DMF	50
8	90	1.1∶1	12	K₃PO₄	DMF	53
9	90	1∶1.1	12	K₃PO₄	DMF	53
10	90	1∶1	12	Na₂CO₃	DMF	45
11	90	1∶1	12	K₂CO₃	DMF	50
12	90	1∶1	12	Cs₂CO₃	DMF	50
13	90	1∶1	12	K₃PO₄	DMAc	51
14	90	1∶1	12	K₃PO₄	1,4-Dioxane	48
15	90	1∶1	12	K₃PO₄	CH₃CN	43

Entry	T/℃	n(5)∶n(6a)	t/h	Base	Solvent	Yield/%
1	80	1∶1	4	K₃PO₄	DMF	18
2	80	1∶1	8	K₃PO₄	DMF	33
3	80	1∶1	12	K₃PO₄	DMF	40
4	80	1∶1	14	K₃PO₄	DMF	40
5	85	1∶1	12	K₃PO₄	DMF	47
6	90	1∶1	12	K₃PO₄	DMF	53
7	100	1∶1	12	K₃PO₄	DMF	50
8	90	1.1∶1	12	K₃PO₄	DMF	53
9	90	1∶1.1	12	K₃PO₄	DMF	53
10	90	1∶1	12	Na₂CO₃	DMF	45
11	90	1∶1	12	K₂CO₃	DMF	50
12	90	1∶1	12	Cs₂CO₃	DMF	50
13	90	1∶1	12	K₃PO₄	DMAc	51
14	90	1∶1	12	K₃PO₄	1,4-Dioxane	48
15	90	1∶1	12	K₃PO₄	CH₃CN	43

Compd.	50 μmol/L		25 μmol/L		15 μmol/L
Compd.	发芽率/%	抑制率/%	发芽率/%	抑制率/%	发芽率/%	抑制率/%
4a	0.0±0.0	100.0±0.0	1.1±1.9	98.8±2.1	63.3±3.3	32.1±3.6
4b	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	61.1±1.9	34.5±2.1
4c	0.0±0.0	100.0±0.0	1.1±1.9	98.8±2.1	65.6±1.9	29.8±2.1
4d	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	67.8±5.1	27.4±5.5
4e	14.4±1.9	84.5±2.1	28.9±5.1	69.0±5.5	—	—
4f	15.6±1.9	83.3±2.1	23.3±3.3	75.0±3.6	—	—
4g	4.4±1.9	95.2±2.1	5.6±1.9	94.0±2.1	—	—
4h	17.8±1.9	81.0±2.1	36.7±3.3	60.7±3.6	—	—
4i	18.9±1.9	79.8±2.1	44.4±3.8	52.4±4.1	—	—
4j	22.2±1.9	76.2±2.1	45.6±1.9	51.2±2.1	—	—
4k	0.0±0.0	100.0±0.0	4.4±1.9	95.2±2.1	71.1±1.9	23.8±2.1
4l	24.4±1.9	73.8±2.1	35.6±3.8	61.9±4.1	—	—
4m	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	55.6±5.1	40.5±5.5
4n	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	57.8±3.8	38.1±4.1
PM4	0.0±0.0	100.0±0.0	11.1±1.9	88.1±2.1	67.8±1.9	27.4±2.1
ABA	2.2±1.9	97.6±2.1	12.2±1.9	86.9±2.1	65.6±5.1	29.8±5.5

Compd.	50 μmol/L		25 μmol/L		15 μmol/L
Compd.	发芽率/%	抑制率/%	发芽率/%	抑制率/%	发芽率/%	抑制率/%
4a	0.0±0.0	100.0±0.0	1.1±1.9	98.8±2.1	63.3±3.3	32.1±3.6
4b	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	61.1±1.9	34.5±2.1
4c	0.0±0.0	100.0±0.0	1.1±1.9	98.8±2.1	65.6±1.9	29.8±2.1
4d	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	67.8±5.1	27.4±5.5
4e	14.4±1.9	84.5±2.1	28.9±5.1	69.0±5.5	—	—
4f	15.6±1.9	83.3±2.1	23.3±3.3	75.0±3.6	—	—
4g	4.4±1.9	95.2±2.1	5.6±1.9	94.0±2.1	—	—
4h	17.8±1.9	81.0±2.1	36.7±3.3	60.7±3.6	—	—
4i	18.9±1.9	79.8±2.1	44.4±3.8	52.4±4.1	—	—
4j	22.2±1.9	76.2±2.1	45.6±1.9	51.2±2.1	—	—
4k	0.0±0.0	100.0±0.0	4.4±1.9	95.2±2.1	71.1±1.9	23.8±2.1
4l	24.4±1.9	73.8±2.1	35.6±3.8	61.9±4.1	—	—
4m	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	55.6±5.1	40.5±5.5
4n	0.0±0.0	100.0±0.0	0.0±0.0	100.0±0.0	57.8±3.8	38.1±4.1
PM4	0.0±0.0	100.0±0.0	11.1±1.9	88.1±2.1	67.8±1.9	27.4±2.1
ABA	2.2±1.9	97.6±2.1	12.2±1.9	86.9±2.1	65.6±5.1	29.8±5.5

Compd.	Total_score	G_score	D_score	PMF_score	Chem_score
4c	5.51	－166.74	－102.12	－59.40	－23.90
4f	5.11	－171.83	－96.88	－54.43	－20.53
4m	7.24	－199.43	－107.20	~64.71	－24.81
4n	6.70	－186.64	－116.82	~65.42	－22.05
PM4	5.46	－186.69	－110.42	－45.26	－26.53
ABA	6.05	－184.31	－102.74	－48.52	－22.00

吗啉磺酰胺化合物的设计、合成及其抑制大豆萌芽活性的研究

Design and Synthesis of Morpholine Sulfonamide Compound and Its Inhibition on Soybean Seed Germination

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