Synthesis and Antifungal Activity of the Derivatives of Novel Pyrazole Carboxamide and Isoxazolol Pyrazole Carboxylate

Abstract

A series of pyrazole carboxamide and isoxazolol pyrazole carboxylate derivatives were designed and synthesized in this study. The structures of the compounds were elucidated based on spectral data (infrared, proton nuclear magnetic resonance and mass spectroscopy). Then, all of the compounds were bioassayed in vitro against four types of phytopathogenic fungi (Alternaria porri, Marssonina coronaria, Cercospora petroselini and Rhizoctonia solani) using the mycelium growth inhibition method. The results showed that some of the synthesized pyrazole carboxamides displayed notable antifungal activity. The isoxazole pyrazole carboxylate 7ai exhibited significant antifungal activity against R. solani, with an EC50 value of 0.37 μg/mL. Nonetheless, this value was lower than that of the commercial fungicide, carbendazol.

Synthesis and Pharmacological Activities of Pyrazole Derivatives: A Review

“…A series of isoxazolol pyrazole carboxylate derivatives were synthesized and bioassayed in vitro against four types of phytopathogenic fungi ( Alternaria porri , Marssonina coronaria , Cercospora petroselini and Rhizoctonia solani ). The results showed that the compound 194 exhibited significant antifungal activity against R. solani , with an EC 50 value of 0.37 μg/mL [ 98 ]. A series of novel diterpene derivatives containing pyrazole ring were synthesized and investigated for their activity against S. aureus Newman strain and multidrug-resistant strains ( NRS-1 , NRS-70 , NRS-100 , NRS-108 and NRS-271 ).…”

Novel Pyrazole-Hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity

“…In recent years, literature revealed that pyrazole derivatives had a wide range of biological activities, such as antibacterial [ 5 , 6 , 7 ], fungicidal [ 8 , 9 , 10 ], insecticidal [ 10 , 11 , 12 , 13 ], antiviral [ 14 , 15 ], and herbicidal [ 16 , 17 ] activities. In our previous work, we reported a series of pyrazole derivatives which had better insecticidal activity against Plutella xylostella [ 18 ].…”

“…A few of the pyrazole-hydrazone derivatives have also been reported and possess various biological activities such as antibacterial [ 25 ], antifungal [ 21 ], anticancer [ 26 ], antioxidant [ 27 ], anti-inflammatory [ 28 ], antitumor and antiangiogenesis [ 29 ] and antiplatelet activities [ 30 ]. In addition, isoxazole, a five membered heterocyclic ring, was an important scaffold for synthesis of various natural compounds and their congeners and had a broad spectrum of pharmacological activities like antibacterial [ 31 ], antifungal [ 9 , 32 , 33 ], insecticide [ 34 , 35 ], and antiviral [ 36 ] activities.…”

Crystal structure and Hirshfeld surface analysis of 1-(2,4-dichlorobenzyl)-5-methyl-N-(thiophene-2-sulfonyl)-1H-pyrazole-3-carboxamide

“…The pyrazole core structure has been widely used as a common heterocyclic scaffold in medicinal chemistry to produce novel drug candidates with a great variety of pharmacological activities including anti-inflammatory, antiplatelet, anticancer, antimycobacterial, antidepressant and anticonvulsant properties (Kü çü kgü zel & Ş enkardeş, 2015;Ç alışkan et al, 2013;Ding et al, 2009;Baraldi et al, 2004;Palaska et al, 2008). Among them, pyrazole-carboxamide derivatives have been shown to exhibit antimycobacterial, antifungal and antiviral activities (Sun & Zhou, 2015;Yan et al, 2018;Comber et al, 1992). In the course of our ongoing research into bioactive pyrazole derivatives (Banog lu et al, 2005;Ş ü kü rog lu et al, 2005;Ergü n et al, 2010;Ç alışkan et al, 2011;Levent et al, 2013;Cankara Pirol et al, 2014), we have relied on the aforementioned biological properties of pyrazole-carboxamides and designed novel pyrazole-3-carboxamide derivatives for their potential antimicrobial activity.…”