新型Pyrabactin类似物的设计、合成及种子萌发抑制活性

doi:10.6023/cjoc201807057

有机化学 ›› 2019, Vol. 39 ›› Issue (2): 419-426.DOI: 10.6023/cjoc201807057 上一篇下一篇

研究论文

新型Pyrabactin类似物的设计、合成及种子萌发抑制活性

车传亮, 胡益敏, 丁珊珊, 肖玉梅, 李佳奇, 覃兆海

中国农业大学理学院北京 100193

收稿日期:2018-07-31 修回日期:2018-08-25 发布日期:2018-10-12
通讯作者: 覃兆海 E-mail:qinzhaohai@263.net
基金资助:
国家自然科学基金（No.21572265）资助项目.

Design, Synthesis and Inhibition Activity of Seed Germination of Novel Pyrabactin Analogs

Che Chuanliang, Hu Yimin, Ding Shanshan, Xiao Yumei, Li Jiqia, Qin Zhaohai

College of Science, China Agricultural University, Beijing 100193

Received:2018-07-31 Revised:2018-08-25 Published:2018-10-12
Contact: 10.6023/cjoc201807057 E-mail:qinzhaohai@263.net
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572265).

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摘要/Abstract

为了开发结构更为稳定的脱落酸脱落酸（ABA）类似物，以Pyrabactin和2'，3'-benzo-iso-ABA（iso-PhABA）为先导，利用类同合成的策略设计了一类新型的磺酰胺类化合物.以1-四氢萘酮为原料，经过羰基α位的甲基化、苄位氧化、羰基腙化和磺酰胺化四步，合成了13个结构新颖的磺酰胺类化合物，并对磺酰胺化的反应条件进行了探索优化.抑制种子萌发的生测结果表明，在浓度为50 μmol·L^-1时，目标化合物具有不同程度的抑制活性，其中有5个化合物对拟南芥和莴苣种子萌发的抑制率分别大于50%和40%.该结果对于新型脱落酸类合成植物激素的创制具有一定的借鉴意义.

关键词: Pyrabactin类似物, 磺酰胺类, 脱落酸类似物, 抑制种子萌发, 类同合成

In order to develop more stable abscisic acid (ABA) analogs, a novel type of sulfonamide compounds was designed based on the similar synthesis strategy using pyrabactin and 2',3'-benzo-iso-ABA (iso-PhABA) as precursors. Using 1-tetralone as raw material, 13 novel sulfonamides were synthesized by methylation, benzylic oxidation, hydrazone formation and sulfonamidation, and the reaction conditions of sulfonamidation were explored and optimized. The results of seed germination experiments showed that the target compounds exhibited different inhibition activities at a concentration of 50 μmol·L^-1, and the inhibition rates of five compounds on Arabidopsis and lettuce seeds germination were greater than 50% and 40%, respectively. These results have important reference significance for the creation of new abscisic acid synthetic phytohormones.

Key words: pyrabactin analogs, sulfonamide, abscisic acid analogs, inhibition of seed germination, similar synthesis

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车传亮, 胡益敏, 丁珊珊, 肖玉梅, 李佳奇, 覃兆海. 新型Pyrabactin类似物的设计、合成及种子萌发抑制活性[J]. 有机化学, 2019, 39(2): 419-426.

Che Chuanliang, Hu Yimin, Ding Shanshan, Xiao Yumei, Li Jiqia, Qin Zhaohai. Design, Synthesis and Inhibition Activity of Seed Germination of Novel Pyrabactin Analogs[J]. Chin. J. Org. Chem., 2019, 39(2): 419-426.

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新型Pyrabactin类似物的设计、合成及种子萌发抑制活性

Design, Synthesis and Inhibition Activity of Seed Germination of Novel Pyrabactin Analogs

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