Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model

Abstract

2020) Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model, Journal of Enzyme Inhibition and Medicinal Chemistry, 35:1, 682-691, ABSTRACTThirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against Oomycete fungi Phytophthora capsici in vitro and in vivo. Interestingly, compound I-1, I-2, I-3, I-6 and I-7 exhibited moderate control effect (>50%) against Pseudoperonospora cubensis in greenhouse at 6.25 lg/ mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against P. capsici. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against Sclerotinia sclerotiorum, P. piricola and R. solan in vitro with EC 50 values of 3.74-9.76 lg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides. ARTICLE HISTORY

Uncovering New Drug Properties in Target-Based Drug–Drug Similarity Networks

“…Furthermore, carbamates are reversible acetylcholinesterase inhibitors that act as effective fungicides, insecticides, and herbicides in agriculture [ 74 ]. Indeed, a recent reference reports the synthesis, in vitro, and in vivo antifungal evaluation of 36 novel threoninamide carbamate derivatives using the pharmacophore model [ 93 ].…”

Isolation, Synthesis, and Fungicidal Activity of Isopropyl (3-methyl-1-oxo-1-((1-((4-(prop-2-yn-1-yloxy)phenyl)thio)propan-2-yl)amino)butan-2-yl)carbamate Diastereomers against Phytophthora capsici

“…e in vitro fungicidal activities of the four compounds 4a, 4b, 4c, and 4d against Phytophthora capsici were evaluated using the mycelium growth rate method [18]. e culture media, with known concentrations (50, 25, 12.5, 6.25, 3.125, 1.56, 0.78, 0.39, 0.2, 0.1, 0.05, 0.025 mg/L) of the test compounds, were obtained by mixing the 1% tween-20 water suspension (1 mL) of high active compounds with potato dextrose agar (PDA, 9 mL) at 50 °C.…”

Synthesis and Bioactivity Evaluation of Novel Thiochroman-4-One Derivatives Incorporating Carboxamide and 1, 3, 4-Thiadiazole Thioether Moieties

“…In our previous study, we disclosed a series of novel thiochroman-4-one derivatives (Figure 1) which showed moderate to good antibacterial and antifungal activities [11][12][13][14]. e carboxamide moiety, an important functional group in pesticide chemistry, had attracted more and more attention to the researchers due to its broad spectrum of pesticidal bioactivities, for example, antibacterial [15,16], antifungal [17,18], antiviral [19][20][21], insecticidal [22,23], and herbicidal [24] properties. Over the past few decades, many new pesticides containing carboxamide moiety, such as fluxapyroxad, penflufen, and isoflucypram, had been developed.…”