1046152-05-9Relevant academic research and scientific papers
Development of 1,5-Diaryl-Pyrazole-3-Formate Analogs as Antifungal Pesticides and Their Application in Controlling Peanut Stem Rot Disease
Ma, Yihui,Qin, Guangyu,Yang, Dangwei,Yang, Jun,Zu, Junhuai
, (2022/01/26)
Stem rot disease caused by Sclerotium rolfsii is one of the destructive diseases in peanut and poses a big risk to peanut production. Current fungicides in the market have not provided satisfactory control efficacy and thus called for novel fungicides with different structures as an alternative treatment strategy. Our previously developed phenylpyrazole compound 3c demonstrated modest inhibitory effect against S. rolfsii. The following structure modification identified an unreported compound 6, which bears a 3-chloropyridinyl moiety as the most prominent derivative with an IC50 of 12 μg/ml in potato dextrose agar (PDA) assay, higher than those of 0.8 and 1.8 μg/ml associated with thifluzamide and tebuconazole, respectively. However, compound 6 showed similar controlling effects to those of thifluzamide and tebuconazole in field study. This study underscores the potential of 1,5-diaryl-pyrazole-3-formate as an antifungal candidate for stem rot disease management.
Diazen-1-ium-1,2-diolated nitric oxide donor ester prodrugs of 1-(4-methanesulfonylphenyl)-5-aryl-1H-pyrazol-3-carboxylic acids: Synthesis, nitric oxide release studies and anti-inflammatory activities
Abdellatif, Khaled R.A.,Chowdhury, Morshed Alam,Dong, Ying,Knaus, Edward E.
, p. 6528 - 6534 (2008/12/22)
A new group of hybrid nitric oxide-releasing anti-inflammatory drugs (NONO-coxibs) wherein an O2-acetoxymethyl-1-(N-ethyl-N-methylamino)diazen-1-ium-1,2-diolate (11a-c) NO-donor moiety is attached directly to the carboxylic acid group of 1-(4-methanesulfonylphenyl)-5-aryl-1H-pyrazol-3-carboxylic acids were synthesized. The diazen-1-ium-1,2-diolate compounds 11a-c all released a low amount of NO upon incubation with phosphate buffer (PBS) at pH 7.4 (7.7-9.3% range). In comparison, the percentage of NO released was significantly higher (67.5-73.6% of the theoretical maximal release of two molecules of NO/molecule of the parent hybrid ester prodrug) when the diazen-1-ium-1,2-diolate ester prodrugs were incubated in the presence of rat serum. These incubation studies suggest that both NO and the anti-inflammatory 1-(4-methanesulfonylphenyl)-5-(4-H, 4-F or 4-Me-phenyl)-1H-pyrazol-3-carboxylic acid (9a-c) would be released from the parent NONO-coxib upon in vivo cleavage by non-specific serum esterases. The 1-(4-methanesulfonylphenyl)-5-(4-H, 4-F or 4-Me-phenyl)-1H-pyrazol-3-carboxylic acids (9a-c) exhibited AI activities (ID50 = 85.2-104.4 mg/kg po range) between that exhibited by the reference drugs aspirin (ID50 = 128.7 mg/kg po) and celecoxib (ID50 = 10.8 mg/kg po). Hybrid ester anti-inflammatory/NO-donor prodrugs (NONO-coxibs) offers a potential drug design concept targeted toward the development of anti-inflammatory drugs that are devoid of adverse ulcerogenic and/or cardiovascular effects.
