新型取代苯基噁唑类化合物的设计、合成及生物活性

通过活性亚结构拼接方法,将具有生物活性的噁唑基团与咪唑烷或噻唑烷拼接,设计合成了一系列新型取代苯基噁唑类化合物.以取代的苯甲酸为原料,经过3步反应制得目标化合物,其结构经核磁共振及元素分析确证.初步生物测定结果表明,部分化合物对小麦赤霉病、水稻纹枯病、黄瓜灰霉病和番茄早疫病表现出明显的抑制活性,尤其是化合物5q表现出较广的杀菌谱,且活性与多氧霉素相当.初步构效关系分析发现,苯环上取代基的类别和位置对活性有影响,其中卤素取代基对活性有利,邻位取代优于对位和间位取代.

Design,Synthesis and Biological Activity of Novel Substituted Phenyl Oxazol Based Compounds

Several famous bioactive heterocycles such as oxazole, imidazolidine and thiazolidine are widely used in both pharmaceutical and pesticide industry. To find new lead compounds with favorable biological activities, a series of novel substituted phenyl oxazol based compounds containing 2-nitroaminoimidazoline or thiazolidine was designed via the method of linking active sub-structures. The target compounds were synthesized from substituted benzoic acid in three steps. Their structures were confirmed by 1H NMR and elemental analysis. The preliminary bioassay results indicated that some target compounds showed obvious inhibitory activities against Gibberella saubinetii, Rhizoctonia solani, Botrytis cinerea and Alternaria solan. Especially, compound 5q, with 62% and 86% inhibition rate against Gibberella saubinetii and Botrytis cinerea, respectively, exhibited equivalent activity to Polyoxin B with 57% and 85% inhibition rate at a concentration of 100 μg/mL. The structure-activity relationship indicated that the type and position of substituent on the benzene ring would influence the activity obviously. The halogen substituent was favorable to activity. Besides, compounds with ortho-substituent showed better activity than those with meta or para-substituent.