Design, Synthesis, and Biological Activity of Novel Chalcone Derivatives Containing an 1,2,4-Oxadiazole Moiety

Abstract

To discover a lead compound for agricultural use, 34 novel chalcone derivatives containing an 1,2,4-oxadiazole moiety were designed and synthesized. Their nematocidal activities against Bursaphelenchus xylophilus, Aphelenchoides besseyi, and Ditylenchus dipsaci and their antiviral activities against tobacco mosaic virus (TMV), pepper mild mottle virus (PMMoV), and tomato spotted wilt virus (TSWV) were evaluated. Biological assay results indicate that compounds A13 and A14 showed good nematocidal activities against B. xylophilus, A. besseyi, and D. dipsaci, with LC50 values of 35.5, 44.7, and 30.2 μg/ml and 31.8, 47.4, and 36.5 μg/ml, respectively, which are better than tioxazafen, fosthiazate, and abamectin. Furthermore, compound A16 demonstrated excellent protective activity against TMV, PMMoV, and TSWV, with EC50 values of 210.4, 156.2, and 178.2 μg/ml, respectively, which are superior to ningnanmycin (242.6, 218.4, and 180.5 μg/ml).

Design, synthesis, and anti-hepatocellular carcinoma of thiopyrimidine/chalcone hybrids as dual STAT3/STAT5 inhibitors

“…Furthermore, a molecular docking study elucidated further details of the process by which 5h binds to the STAT3 and STAT5 SH2 domains. The chalcones 3a-i 43,44 and the acylated chalcones 4a-h 43 are synthesized as reported and their structures were validated by reported melting points. 4.2.3.…”

Design, Synthesis, Nematicidal Activity, and Mechanism of Novel Amide Derivatives Containing an 1,2,4-Oxadiazole Moiety

“…Intermediates 1d – 13d were synthesized as reported in the literature . Under ice-bath conditions, triethylamine (22.5 mmol) was added dropwise to the mixture of intermediate b (7.50 mmol) and toluene (20 mL) with stirring.…”

1,2,4-Oxadiazole as a potential scaffold in agrochemistry: a review

“…Apart from that, several 1,2,4-oxadiazole derivatives fused with chalcone were synthesized. 80 Based on the results, compounds 63 and 64 showed good nematicidal activities against B. xylophilus , Aphelenchoides besseyi , and Ditylenchus dipsaci with LC 50 values of 35.5, 44.7, and 30.2 μg mL −1 , respectively.…”

“…Apart from that, several 1,2,4-oxadiazole derivatives fused with chalcone were synthesized. 80 A novel class of oxadiazole compounds was synthesized by Luo's group in 2023. 81 For instance, as depicted in Fig.…”