Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol

Abstract

Background Plant diseases caused by viruses and bacteria cause huge economic losses due to the lack of effective control agents. New potential pesticides can be discovered through biomimetic synthesis and structural modification of natural products. A series of ferulic acid derivatives containing an β-amino alcohol were designed and synthesized, and their biological activities were evaluated. Result Bioassays results showed that the EC50 values of compound D24 against Xanthomonas oryzae pv. oryzae (Xoo) was 14.5 μg/mL, which was better than that of bismerthiazol (BT, EC50 = 16.2 μg/mL) and thiodiazole copper (TC, EC50 = 44.5 μg/mL). The in vivo curative and protective activities of compound D24 against Xoo were 50.5% and 50.1%, respectively. The inactivation activities of compounds D2, D3 and D4 against tobacco mosaic virus (TMV) at 500 μg/mL were 89.1, 93.7 and 89.5%, respectively, superior to ningnanmycin (93.2%) and ribavirin (73.5%). In particular, the EC50 value of compound D3 was 38.1 μg/mL, and its molecular docking results showed that compound D3 had a strong affinity for TMV-CP with a binding energy of − 7.54 kcal/mol, which was superior to that of ningnanmycin (− 6.88 kcal /mol). Conclusions The preliminary mechanism research results indicated that compound D3 may disrupt the three-dimensional structure of the TMV coat protein, making TMV particles unable to self-assemble, which may provide potential lead compounds for the discovery of novel plant antiviral agents. Graphical Abstract

Trifluoromethylpyridine piperazine derivatives: synthesis and anti‐plant virus activity

“…Taking Chenopodium amaranticolor as the experimental plant, the anti‐CMV activities of the target compounds were tested by the half‐leaf method at 500 μg mL −1 17,19,20 . At the same time, for the compounds with special activities, their activities at 500, 250, 125, 62.5, and 31.25 μg mL −1 were tested, and the half maximal effective concentration (EC 50 ) value was calculated 21 …”

“…Taking Chenopodium amaranticolor as the experimental plant, the anti-CMV activities of the target compounds were tested by the half-leaf method at 500 μg mL −1 . 17,19,20 At the same time, for the compounds with special activities, their activities at 500, 250, 125, 62.5, and 31.25 μg mL −1 were tested, and the half maximal effective concentration (EC 50 ) value was calculated. 21 3.1.1 Curative activity of target compounds against CMV Using plants with the same growth cycle, the carborundum powder was spread evenly on the leaves, the viruses were gently brushed on the leaves with a brush, and after 30 min of virus action, the carborundum powder was washed off with water.…”

Ferulic Acid: A Natural Phenol That Inhibits Neoplastic Events through Modulation of Oncogenic Signaling

“…It has been reported that the biological activity of ferulic acid can be altered by creating its derivatives. A series of such derivatives of ferulic acid with β-amino alcohol has been previously reported ( Figure 1 ) [ 16 ]. The chemical structure of ferulic acid has the presence of benzene rings with a carboxylic group.…”

Synthesis, biological evaluation, and molecular docking of novel ferulic acid derivatives containing a 1,3,4-oxadiazole thioether and trifluoromethyl pyrimidine skeleton

“…5–8 Among them, ferulic acid is a natural plant metabolite that is usually found in Ferula assa-foetida L., Ligusticum chuanxiong Hort., Catalpa ovata G. Don 9 and so on. Ferulic acid is a phenylpropanoid natural product containing a phenolic hydroxyl group and has a great variety of pharmacological activities, such as herbicidal, 10,11 fungicidal, 12,13 antiviral, 14,15 and bactericidal 16–18 activities. Therefore, ferulic acid derivatives are a class of lead compounds designed and synthesized for new pesticides.…”