Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives

doi:10.6023/cjoc201708004

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 509-518.DOI: 10.6023/cjoc201708004 Previous Articles Next Articles

Notes

新型含氟酰胺化羟甲香豆素衍生物的合成及生物活性

乔丽丽, 魏艳, 郝双红

青岛农业大学化学与药学院山东省农业仿生应用工程技术研究中心青岛 266109

收稿日期:2017-08-17 修回日期:2017-10-10 发布日期:2017-10-20
通讯作者: 郝双红 E-mail:doublered74@sina.com
基金资助:
国家自然科学基金（No.31471808）资助项目.

Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives

Qiao Lili, Wei Yan, Hao Shuanghong

Research Center of Agro-bionic Engineering & Technology of Shandong Province, College of Chemistry & Pharmacy, Qingdao Agricultural University, Qingdao 266109

Received:2017-08-17 Revised:2017-10-10 Published:2017-10-20
Contact: 10.6023/cjoc201708004 E-mail:doublered74@sina.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31471808).

1. Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives.PDF(2598KB)

Abstract

Based on the structure of lead compound of 7-hydroxy-4-methyl-coumarin, a series of novel fluorinated amide coumarin derivatives were designed and synthesized through the principle of bioactive substructure combination. Their structures were characterized by ¹H NMR, ¹³C NMR and HRMS. N-(n-Butyryl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluo-romethyl-coumarin (f1) and N-(p-methylbenzoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f9) were further confirmed by X-ray single crystal diffraction. The results of herbicidal activity indicated that compounds f1, N-phenylacetyl-N-(m-fluorobenzyl)-6-amino-7-methyloxy-4-trifluoromethyl-coumarin (f13), N-methylacryloyl-N-(m-fluoro-benzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f5), N-(cyclopropylcarbonyl)-N-(m-fluorobenzyl)-6-amino-7-meth-oxy-4-trifluoromethyl-coumarin (f7), N-(6-chloronicotinoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-cou-marin (f20), exhibited marked inhibition against the stem growth of Digitaria sanguinalis. And f9, f7, N-(naphthalene-2-carbonyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f17) showed excellent inhibition on the stem of Chenopodium glaucum. The herbicidal activities of the compounds mentioned above were more active than the commercial herbicide acetochlor. The results of crop safety evaluation showed that compounds f1、f9 and f13 were safe to Brassica pekinensis and Brassica napus but sensitive to Triticum aestivum and Sorghum bicolor. Furthermore, N-(m-bromobenzoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f12), f7 and f9 were medium active against the mycelium of phytopathogenic fungi Botrytis cinerea. And N-(hydrocinnamoyl)-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin (f14) was medium active to Valsa mali.

Key words: N-acyl-N-(m-fluorobenzyl)-6-amino-7-methoxy-4-trifluoromethyl-coumarin derivatives, synthesis, herbicidal activity, antifungal activity

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Qiao Lili, Wei Yan, Hao Shuanghong. Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives[J]. Chin. J. Org. Chem., 2018, 38(2): 509-518.

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新型含氟酰胺化羟甲香豆素衍生物的合成及生物活性

Synthesis and Biological Activity of Novel Fluorinated Amide Hydroxy Methyl Coumarin Derivatives

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