Design, synthesis, fungicidal property and QSAR studies of novel β‐carbolines containing urea, benzoylthiourea and benzoylurea for the control of rice sheath blight

Abstract

Based on the bioassay result and quantitative structure-activity relationship (QSAR) information, structure modification in β-carboline warrants further investigation and its benzoylurea derivative 17c, which showed the best fungicidal activities, could emerge as a potential fungicide against rice sheath blight. © 2018 Society of Chemical Industry.

Synthesis, Crystal Structure, Antifungal Activity, and Docking Study of Difluoromethyl Pyrazole Derivatives

“…On the other hand, urea structure also is an important skeleton in bioactive molecules. The urea derivatives also exhibited diverse bioactivities, such as mosquito activity , antimicrobial activity , antiviral activity , antifungal activity , antinociceptive activity , and anticancer activity .…”

Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight

“…Of these compounds, indole (7, EC 50 = 25.56 µg/mL) displayed superior fungicidal activity, and was 7-fold as potent as validamycin A (EC 50 = 183.00 µg/mL). Additionally, it can be seen quite clearly that the structural changes in general were detrimental to activity and no favorable substitution could be found for the 2-or 3-position, even after extensive probing with a variety of diverse groups (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26). These findings implied that indole was a potent fungicidal template for further modification and derivatization.…”

“…The fungi R. solani GD-118 was provided by our laboratory, and the rice cultivar (Xiangyazhan) was planted according to our previously reported method [15]. The in vitro and in vivo fungicidal activity against R. solani were tested following our previously reported method [17].…”

“…For instant, the representative harmala alkaloids harmine (Figure 1, 1), harmaline (2) and tetrahydroharmine (3) displayed marginal and similar fungicidal activity against R. solani [13]. In our previous work, we had introduced urea [15] and oxadiazole [16] groups into the 3 position of β-carboline scaffold and obtained two potent compounds 5 and 6 with respective EC50 values of 69.52 and 4.24 μg/mL against R. solani. Continued exploration of the β-carboline through optimization of the ring C of β-carboline led to 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene derivatives with greater fungicidal efficacy giving rise to a highly effective agent 4 (EC50 = 2.35 μg/mL) [17], which indicated that the ring C of β-carboline was attractive for further simplifications.…”

3,3-Bis(2-hydroxyethyl)-1-(4-methylbenzoyl)thiourea: crystal structure, Hirshfeld surface analysis and computational study

“…Thiourea molecules are of interest in themselves and as ligands for metal ions (Saeed et al, 2014). The free molecules, including benzoyl derivatives, are well-known to exhibit various biological properties, for example, anti-bacterial, antifungal and anti-viral activities as well as cytotoxicity (Hallur et al, 2006;Cunha et al, 2007;Saeed et al, 2010;Gunasekaran et al, 2017;Zhang et al, 2018;. The combination of hard (oxygen) and soft (sulfur) donor atoms along with nitrogen suggests that benzoylthioureas can function as versatile ligands to metals.…”