喹啉-6-磺酰胺类化合物的设计、合成及其抑制大豆种子萌芽活性的研究

doi:10.6023/cjoc202206040

有机化学 ›› 2022, Vol. 42 ›› Issue (9): 2947-2953.DOI: 10.6023/cjoc202206040 上一篇下一篇

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喹啉-6-磺酰胺类化合物的设计、合成及其抑制大豆种子萌芽活性的研究

黄志友^a^,^b^,^*(), 张宁^a, 左涵文^a, 曾旭祺^a, 刘涵^a

a 邵阳学院城乡建设学院湖南邵阳 422000
b 华中师范大学化学学院武汉 430079

收稿日期:2022-06-21 修回日期:2022-07-23 发布日期:2022-08-10
通讯作者: 黄志友
基金资助:
湖南省自然科学基金青年项目(2021JJ40515); 湖南省教育厅研究(21B0677)

Design, Synthesis and Seed Germination Inhibition Activity of Quinoline-6-sulfonamide Compounds

Zhi-You Huang^a^,^b(), Ning Zhang^a, Han-Wen Zuo^a, Xu-Qi Zeng^a, Han Liu^a

a College of Urban and Rural Construction, Shaoyang University, Shaoyang, Hunan 422000
b College of Chemistry, Central China Normal University, Wuhan 430079

Received:2022-06-21 Revised:2022-07-23 Published:2022-08-10
Contact: Zhi-You Huang
Supported by:
Natural Science Foundation of Hunan Province Youth Project(2021JJ40515); Scientific Research Fund of Hunan Provincial Education Department(21B0677)

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摘要/Abstract

为了发现结构新颖的脱落酸功能类似物, 以小分子abscisic mimic 1 (AM1)和Pyrabactin为先导化合物, 运用活性亚结构拼接原理设计了喹啉-6-磺酰胺类化合物3和4. 以廉价易得的喹啉为起始原料, 经成盐、氧化、去芳香化、磺酰化、胺化5步反应, 合成了11个未见文献报道的新型类似物. 种子萌芽试验结果表明, 浓度为50 µmol•L^–1时10个化合物明显抑制了大豆种子发芽, 降低浓度至25 µmol•L^–1时仍有4个化合物完全抑制萌芽, 其活性与AM1相当, 并且优于脱落酸. 该结果有利于发现高活性的新型脱落酸功能类似物.

关键词: 喹啉-6-磺酰胺, 脱落酸类似物AM1, Pyrabactin, 抑制萌芽

To develop novel abscisic acid (ABA) functional mimics, a series of quinoline-6-sulfonamide compounds 3 and 4 was designed based on the principle of active substructure splicing with ABA mimic 1 (AM1) and pyrabactin as lead compounds. The low-cost and commercial quinoline was used as starting material to offer the novel compounds via the salifying, oxidation, hydrogenation, sulfonylation, amination. Additionally, all the target compounds could inhibit soybean seed germination at the concentration of 50 µmol•L^–1. Furthermore, the compounds 3, 4b, 4h, 4i could inhibit soybean seed germination overwhelmingly at 25 µmol•L^–1. These results are benefit to discovering novel and high activity of ABA functional mimics.

Key words: quinoline-6-sulfonamide, abscisic mimic 1 (AM1), pyrabactin, inhibition seed germination

引用此文

黄志友, 张宁, 左涵文, 曾旭祺, 刘涵. 喹啉-6-磺酰胺类化合物的设计、合成及其抑制大豆种子萌芽活性的研究[J]. 有机化学, 2022, 42(9): 2947-2953.

Zhi-You Huang, Ning Zhang, Han-Wen Zuo, Xu-Qi Zeng, Han Liu. Design, Synthesis and Seed Germination Inhibition Activity of Quinoline-6-sulfonamide Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2947-2953.

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Compd.	50 μmol/L		25 μmol/L		15 μmol/L
Compd.	抑制率	发芽率	抑制率	发芽率	抑制率	发芽率
3	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	41.4±2.5	45.6±1.9
4a	78.6±4.3	16.7±3.3	52.9±4.3	36.7±3.3	—	—
4b	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	44.3±4.3	43.3±3.3
4c	81.4±2.5	14.4±1.9	48.6±4.3	40.0±3.3	—	—
4d	100.0±0.0	0.0±0.0	81.4±2.5	14.4±1.9	—	—
4e	100.0±0.0	0.0±0.0	77.1±2.5	17.8±1.9	—	—
4f	65.7±4.3	26.7±3.3	31.4±4.3	53.3±3.3	—	—
4g	60.0±2.5	31.1±1.9	28.6±2.5	55.6±1.9	—	—
4h	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	34.3±2.5	51.1±1.9
4i	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	30.0±6.5	54.4±5.1
4j	37.1±4.9	48.9±3.8	5.7±4.3	73.3±3.3	—	—
AM1	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	48.6±4.3	40.0±3.3
ABA	100.0±0.0	0.0±0.0	84.3±2.5	12.2±1.9	38.6±4.9	47.8±3.8
CK	77.8±1.9 (0.5% DMSO)

Compd.	50 μmol/L		25 μmol/L		15 μmol/L
Compd.	抑制率	发芽率	抑制率	发芽率	抑制率	发芽率
3	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	41.4±2.5	45.6±1.9
4a	78.6±4.3	16.7±3.3	52.9±4.3	36.7±3.3	—	—
4b	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	44.3±4.3	43.3±3.3
4c	81.4±2.5	14.4±1.9	48.6±4.3	40.0±3.3	—	—
4d	100.0±0.0	0.0±0.0	81.4±2.5	14.4±1.9	—	—
4e	100.0±0.0	0.0±0.0	77.1±2.5	17.8±1.9	—	—
4f	65.7±4.3	26.7±3.3	31.4±4.3	53.3±3.3	—	—
4g	60.0±2.5	31.1±1.9	28.6±2.5	55.6±1.9	—	—
4h	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	34.3±2.5	51.1±1.9
4i	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	30.0±6.5	54.4±5.1
4j	37.1±4.9	48.9±3.8	5.7±4.3	73.3±3.3	—	—
AM1	100.0±0.0	0.0±0.0	100.0±0.0	0.0±0.0	48.6±4.3	40.0±3.3
ABA	100.0±0.0	0.0±0.0	84.3±2.5	12.2±1.9	38.6±4.9	47.8±3.8
CK	77.8±1.9 (0.5% DMSO)

喹啉-6-磺酰胺类化合物的设计、合成及其抑制大豆种子萌芽活性的研究

Design, Synthesis and Seed Germination Inhibition Activity of Quinoline-6-sulfonamide Compounds

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