背景:面对需要开发新的除草剂,其作用方式与现有农用化学品的作用方式不同,合成化学家采用的最有前途的策略之一是对天然产物中的分子进行结构修饰。含有酰胺的分子,酰亚胺,和环氧化物作为官能团在自然界中普遍存在,并由于其生物学特性而在合成更复杂的化合物中得到了广泛的应用。在这种情况下,本文介绍了N-苯基降冰片烯琥珀酰亚胺衍生物的合成,进行生物测定,并对与植物生物中最有效的化合物相关的蛋白质靶标进行了计算机模拟研究。在洋葱上评估了合成化合物(2-29)的植物毒性作用,Bidenspilosa,黄瓜,双色高粱和番茄红素。
结果:内双环[2.2.1]hept-5-ene-3a的反应,7a-二羧酸酐(1)与芳族胺产生N-苯基降冰片烯琥珀酸(2-11),产率为75-90%。在乙酸酐和乙酸钠存在下环化化合物(2-11),得到N-苯基降冰片烯琥珀酰亚胺(12-20),产率为65-89%。那些酰亚胺当时是,进行环氧化反应,得到N-苯氧基降冰片酰亚胺(21-29),产率为60-90%。所有化合物均抑制所评估植物幼苗的生长。物质(23)对测试的植物最活跃,100%抑制所有浓度的所有物种的生长。发现亲环蛋白是化合物(23)的酶靶标。
结论:这些发现表明,N-苯基降冰片烯琥珀酰亚胺的衍生物是寻求更具选择性和稳定性的农用化学品的有希望的化合物。这种观点加强了这些衍生物作为潜在创新除草剂的重要性,并强调了进一步探索其对杂草的生物活性的重要性。本文受版权保护。保留所有权利。
BACKGROUND: Faced with the need to develop new herbicides with modes of action different to those observed for existing agrochemicals, one of the most promising strategies employed by synthetic chemists involves the structural modification of molecules found in natural products. Molecules containing amides, imides, and epoxides as functional groups are prevalent in nature and find extensive application in synthesizing more intricate compounds due to their biological properties. In this context, this paper delineates the synthesis of N-phenylnorbornenesuccinimide derivatives, conducts biological assays, and carries out in silico investigation of the protein target associated with the most potent compound in plant organisms. The phytotoxic effects of the synthesized compounds (2-29) were evaluated on Allium cepa, Bidens pilosa, Cucumis sativus, Sorghum bicolor, and Solanum lycopersicum.
RESULTS: Reaction of endo-bicyclo[2.2.1]hept-5-ene-3a,7a-dicarboxylic anhydride (1) with aromatic amines led to the N-phenylnorbornenesuccinic acids (2-11) with yields ranging from 75% to 90%. Cyclization of compounds (2-11) in the presence of acetic anhydride and sodium acetate afforded N-phenylnorbornenesuccinimides (12-20) with yields varying from 65% to 89%. Those imides were then subjected to epoxidation reaction to afford N-phenylepoxynorbornanesuccimides (21-29) with yields from 60% to 90%. All compounds inhibited the growth of seedlings of the plants evaluated. Substance 23 was the most active against the plants tested, inhibiting 100% the growth of all species in all concentrations. Cyclophilin was found to be the enzymatic target of compound 23.
CONCLUSIONS: These findings suggest that derivatives of N-phenylnorbornenesuccinimide are promising compounds in the quest for more selective and stable agrochemicals. This perspective reinforces the significance of these derivatives as potential innovative herbicides and emphasizes the importance of further exploring their biological activity on weeds. © 2024 Society of Chemical Industry.