The introduction of fluorine into bioactive molecules is a matter of importance in medicinal chemistry. In this study, representatives of various chemical entities of fluoroaromatic compounds were synthesized. Depending on the reaction conditions, either tetrafluorophthalimides or ammonium tetrafluorophthalamates are accessible from tetrafluorophthalic anhydride and primary amines. Tetrafluorophthalamic acids undergo thermal decarboxylation to yield tetrafluorobenzamides. These could be successfully converted upon treatment with primary amines, in the course of an aromatic nucleophilic substitution, to 2,3,5‐trifluorobenzamides with respective amino substituents at the 4‐position. The five structure types were characterized by means of spectroscopic and crystallographic methods. The synthesized compounds were evaluated as inhibitors of angiogenesis by measuring microvessel outgrowth in a rat aortic ring assay. The biological activity was maintained throughout these different polyfluorinated chemotypes.

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多氟苯甲酰胺的合成，结构表征和抗血管生成活性

将氟引入生物活性分子是药物化学中的重要问题。在这项研究中，合成了氟代芳香族化合物的各种化学实体的代表。根据反应条件，可从四氟邻苯二甲酸酐和伯胺获得四氟邻苯二甲酰亚胺或四氟邻苯二甲酸铵。四氟邻苯二酸经过热脱羧反应生成四氟苯甲酰胺。在芳族亲核取代过程中，用伯胺处理后可以成功地将它们转化为在4位带有相应氨基取代基的2,3,5-三氟苯甲酰胺。通过光谱和晶体学方法表征了五种结构类型。通过在大鼠主动脉环测定中测量微血管的生长，评价合成的化合物作为血管生成的抑制剂。在所有这些不同的多氟化化学型中都保持了生物学活性。