取代的N-苯基吡嗪-2-甲酰胺及其作为除草剂和非生物诱导剂的合成与评价

Substituted N-phenylpyrazine-2-carboxamides, their synthesis and evaluation as herbicides and abiotic elicitors.

作者信息

Dolezal Martin, Tůmová Lenka, Kesetovicová Diana, Tůma Jirí, Králová Katarína

机构信息

Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, Hradec Králové, 500 05, Czech Republic.

出版信息

Molecules. 2007 Dec 20;12(12):2589-98. doi: 10.3390/12122589.

DOI:10.3390/12122589

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6149141/

Abstract

The condensation of substituted pyrazine-2-carboxylic acid chlorides with ring-substituted anilines yielded five substituted pyrazine-2-carboxylic acid amides. Thesynthesis, and analytical, lipophilicity and biological data of the newly synthesizedcompounds are presented in this paper. The photosynthesis inhibition, antialgal activityand the effect of a series of pyrazine derivatives as abiotic elicitors on the accumulation offlavonoids in a callus culture of Ononis arvensis (L.) were investigated. The most activeinhibitor of the oxygen evolution rate in spinach chloroplasts was 6-chloro-pyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2, IC(50) = 51.0 micromol.L(-1)). The highestreduction of chlorophyll content in Chlorella vulgaris was found for 5-tert-butyl-N-(4-chloro-3-methylphenyl)-pyrazine-2-carboxamide (3, IC(50) = 44.0 micromol.L(-1)). The maximalflavonoid production (about 900%) was reached after a twelve-hour elicitation processwith 6-chloropyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2).

摘要

取代的吡嗪 -2- 羧酸氯化物与环取代苯胺缩合得到了五种取代的吡嗪 -2- 羧酸酰胺。本文介绍了新合成化合物的合成、分析、亲脂性和生物学数据。研究了一系列吡嗪衍生物作为非生物诱导剂对田野驴豆愈伤组织培养物中黄酮类化合物积累的光合作用抑制、抗藻活性及影响。菠菜叶绿体中放氧速率最有效的抑制剂是 6-氯 - 吡嗪 -2- 羧酸（3-碘 -4- 甲基苯基）酰胺（2，IC(50) = 51.0 μmol·L(-1)）。对于 5-叔丁基 -N-(4-氯 -3- 甲基苯基）- 吡嗪 -2- 甲酰胺（3，IC(50) = 44.0 μmol·L(-1)），在普通小球藻中叶绿素含量降低最高。用 6-氯吡嗪 -2- 羧酸（3-碘 -4- 甲基苯基）酰胺（2）进行十二小时诱导处理后，黄酮类化合物产量达到最大值（约 900%）。

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