Design, Synthesis, and Antifungal Activity of Novel Thiochromanone Derivatives Containing 1,3,4-Oxadiazole Skeleton

Abstract

Following the principle of union of active group, the thiochromanone was combined with 1,3,4-oxadiazole, and 12 compounds were designed and synthesized. The target compounds were confirmed by 1 H NMR and HRMS. The preliminary antifungal activity assay showed that most of the target compounds exhibited significant inhibition activity against four animal pathogenic fungi and four plant pathogenic fungi. Among them, the minimum inhibitory concentration (MIC) value of compound 4f against Canidia albicans reached 4 μg•mL -1 , and the MIC value of 4d against Aspergillusnigervan tiegh reached 8 μg•mL -1 , which were higher than the positive controls. And the molecular docking studies have found that 4f has strong binding ability to CYP51 of Canidia albicans, which may be a potential CYP51 inhibitor.

Novel Thiochromanone Derivatives Containing a Sulfonyl Hydrazone Moiety: Design, Synthesis, and Bioactivity Evaluation

“…The 1 H-NMR, 13 C-NMR, and HRMS data and spectra for all the synthesized compounds are shown in the Supplementary Materials. substance in the synthesis of various active molecules that are extensively used in the intermediate skeleton of drugs and has attracted more and more attention due to their extensive biological activities, including antiviral [10], antibacterial [11,12], antifungal [11,[13][14][15], herbicidal [16,17], and insecticidal [18] activity. Therefore, due to its excellent features of low toxicity and easy to be synthetized and derived, thiochromanone is considered to be a leading compound to develop promising agrochemical candidates, which will become a reality.…”

“…The singlet in δ = 170.1-170.8 ppm indicated the presence of a C=O group. The 1 H-NMR, 13 C-NMR, and HRMS data and spectra for all the synthesized compounds are shown in the Supplementary Materials.…”

“…Instrument Co., Shanghai, China). 1 H-NMR and 13 C-NMR spectral analyses were performed on a Bruker DRX-400 NMR spectrometer (Bruker, Rheinstetten, Germany). HRMS data were measured on an Agilent Technologies 6210 LC/MS TOF mass spectrometer (Agilent, Palo Alto, CA, USA).…”

“…Meanwhile, biological activity results showed that both natural and synthetic chromone compounds had a wide range of biological activities, such as antifungal [ 6 , 7 ], antibacterial [ 6 ], anticancer [ 8 ], and antiviral [ 9 ] activity. Thiochromanone, a kind of chromone compound, is an important substance in the synthesis of various active molecules that are extensively used in the intermediate skeleton of drugs and has attracted more and more attention due to their extensive biological activities, including antiviral [ 10 ], antibacterial [ 11 , 12 ], antifungal [ 11 , 13 , 14 , 15 ], herbicidal [ 16 , 17 ], and insecticidal [ 18 ] activity. Therefore, due to its excellent features of low toxicity and easy to be synthetized and derived, thiochromanone is considered to be a leading compound to develop promising agrochemical candidates, which will become a reality.…”

Synthesis and Insecticidal Activity of 3-Ethyl Sulfone Pyridine Substituted Aryl Triazole Compounds

“…基吡啶类化合物, 这类杀虫剂的作用机制新颖, 具有一 定的创新性和研究意义 [21][22][23][24] . 例如, 日本住友化学株式 会社开发的 Oxazosulfy [25] , 其在 500 mg/L 浓度下对蚜 虫、 褐飞虱和淡色库蚊防治效果均为 90%, 50 mg/L 浓度 下对烟粉虱、细翅目防治效果均为 100%; 先正达公司 开发的化合物 B [26] , 其在浓度为 24 mg/L 时对西方花蓟 马和 绿桃蚜防治效果均为 80%.…”