Synthesis and Antiviral Activities of Pyrazole Derivatives Containing an Oxime Moiety

Abstract

Target compounds 4a- n were obtained by the reaction of 1-substituted phenyl-3-methyl-5-substituted phenylthio-4-pyrazolaldoximes (3) with chloromethylated heterocyclic compounds (ClCH 2-R 3) under reflux conditions in ethanol. Subsequently, the oxidation of 4a- e with KMnO 4 in HOAc at room temperature afforded eight new compounds, 5a- h. The synthesized compounds were characterized by physical constants, and the structures of the title compounds were confirmed by IR, (1)H NMR, (13)C NMR, and elemental analysis. The bioassay revealed that the compounds possessed antiviral activities. It was found that title compounds 4a and 4g had the same inactivation effects against TMV (EC 50 = 58.7 and 65.3 microg/mL) as the commercial product Ningnanmycin (EC 50 = 52.7 microg/mL). To the best of our knowledge, this is the first report on the antiviral activity of pyrazole derivatives containing an oxime moiety.

Synthesis and anti-bacterial activity of novel 1,3-pheylene-bis-N-acetyl- and N-phenylpyrazole derivatives

“…Several of pyrazole products are available and widely used as fungicides, antiviral agents, analgesic agents, insecticides and herbicides. [9][10][11] For thus, pyrazole derivatives have attracted considerable attention in the recent years for their diverse biological activities. [12][13][14][15][16][17] In this paper, the novel 1,1'-(5,5'-(1,3-phenylene)bis(3-aryl-4,5-dihydro-1H-pyrazole-5,1-diyl))diethanone (5a-e) and 1,3-bis(1-phenyl-3-(aryl)-4,5-dihydro-1H-pyrazol-5-yl)benzene (6a-e) were synthesized in good yields and evaluated the antibacterial activities of compounds (5a-e) against some human pathogenic bacteria.…”

Synthesis, Crystal Structure, and DFT Study of Ethyl 1-(2-(Hydroxyimino)-2-phenylethyl)-3-phenyl-1H-pyrazole-5-carboxylate

“…It has been found that they exhibit various biological activities that are often related to low toxicity and increase a great amount of beneficial influences on human health. Therefore, they have attracted wide interest for decades owing to their diverse biological properties such as insecticidal [1], acaricidal [2], antitumor [3][4][5], fungicidal [6], antiviral [7,8], antibacterial [9][10][11], COX inhibitory [12], and fluorescent [13,14] properties.…”

Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives

“…Pyrazole oximes are an important class of heterocyclic compounds which have drawn intense attention because of their good fungicidal [1,2], insecticidal [3][4][5], acaricidal [6], and anti-tobacco mosaic virus (TMV) activity [7]. For instance, Fenpyroximate (Figure 1), a potent agricultural acaricide with a vital pyrazole oxime backbone in the structure, possesses wonderful acaricidal property against some phytophagous mites such as Polyphagotarsonemus latus Banks and Tetranychus urticae Koch on different crops [8].…”