Laboratory of Green and Medicinal Chemistry, Department of Chemistry and Environmental Sciences, Institute of Biosciences, Humanities and Exact Sciences, São Paulo State University (Unesp), São José do Rio Preto, SP 15054-000, Brazil.
Department of Pediatric Dentistry and Public Health, School of Dentistry, São Paulo State University (Unesp), Araçatuba, SP 16015-050, Brazil.
Molecules. 2017 Oct 10;22(10):1685. doi: 10.3390/molecules22101685.
Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds and exhibited MIC (minimum inhibitory concentration) and MBC (minimum bactericidal concentration) values of 77.9 to 312 µM against , , and Compounds , , , and presented potent effects against (57.2 µM ≤ MIC ≤ 70.9 µM). Hydrophilic effects caused by substituents on ring B increased antibacterial activity against Gram-positive species. Thus, log were calculated by using high-performance liquid chromatography-photodiode array detection (HPLC-PDA) analyses, and cinnamylideneacetophenones presented values ranging from 2.5 to 4.1. In addition, the effects of and were evaluated on pulmonary cells, indicating their moderate toxicity (46.3 µM ≤ IC ≤ 96.7 µM) when compared with doxorubicin. Bioactive compounds were subjected to in silico prediction of pharmacokinetic properties, and did not violate Lipinski's and Veber's rules, corroborating their potential bioavailability by an oral route.
肉桂醛是一种具有广谱抗菌活性的天然产物。在这项工作中，它被用作设计和合成一系列 17 个肉桂亚苄基乙酮的模板。酚类化合物 和 对 、 、 和 表现出 MIC（最小抑菌浓度）和 MBC（最小杀菌浓度）值为 77.9 至 312 µM。化合物 、 、 、 和 对 （57.2 µM ≤ MIC ≤ 70.9 µM）具有很强的作用。B 环上取代基引起的亲水性增加了对抗革兰氏阳性菌的抗菌活性。因此，通过高效液相色谱-光电二极管阵列检测（HPLC-PDA）分析计算了 log ，肉桂亚苄基乙酮的值范围为 2.5 至 4.1。此外，还评估了 和 对肺细胞的作用，与多柔比星相比，它们的毒性适中（46.3 µM ≤ IC ≤ 96.7 µM）。生物活性化合物进行了药代动力学性质的计算机预测，并且不违反 Lipinski 和 Veber 规则，这证实了它们通过口服途径的潜在生物利用度。
