Synthesis, Characterization and Antimicrobial Activity of Certain Novel Aryl Hydrazone Pyrazoline-5-Ones Containing Thiazole Moiety

Reddy, Maliki Reddy Dastagiri; Prasad, A. Raghavendra Guru; Spoorthy, Yadati Narasimha; Ravindranath, Lakshmana Rao Krishna Rao

doi:10.5681/apb.2013.026

Cited by 2 publications

(1 citation statement)

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“…Compounds containing a pyrazolone ring possess anti-inflammatory, analgesic, antibacterial, , hypoglycemic, and antitumor , effects, among them are p38 MAP kinase inhibitors, HIV-1 integrase inhibitors, 4-phosphodiesterase inhibitors, , and HNO donors. , 4,4-Dichloro-1-(2,4-dichlorophenyl)-3-methyl-5-pyrazolone (TELIN) is considered as an active substance for treatment of cancer and related diseases . Several compounds are also registered as drugs: the neuroprotector edaravone (1-phenyl-3-methyl-5-pyrazolone) is effective in acute ischemic stroke and amyotrophic lateral sclerosis, and phenazone derivatives are anti-inflammatory drugs used in many analgesic combinations. , A number of pyrazolones exhibit herbicidal − and fungicidal ,− properties; however, the activity is not associated with the presence of the pyrazolone ring itself, and such molecules contain other moieties essential for the manifested activity. On the other hand, the nitro group is part of the group of antimicrobial drugs (furazolidone, tinidazole, furadonin (nitrofurantoin), and ornidazole) and dinitrophenol pesticide family …”

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confidence: 99%

4-Nitropyrazolin-5-ones as Readily Available Fungicides of the Novel Structural Type for Crop Protection: Atom-Efficient Scalable Synthesis and Key Structural Features Responsible for Activity

Budnikov

Lopat’eva

Krylov

et al. 2022

J. Agric. Food Chem.

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The development of new types of fungicides for agriculture and medicine is highly desirable due to the uprising fungal resistance against commonly used compounds. Herein, 4-substituted-4-nitropyrazolin-5-ones (nitropyrazolones) were proposed as highly active fungicides of the novel structural type. The first scalable and practical method for the nitropyrazolone synthesis was proposed, which is atom-efficient, is applicable for the multigram scale synthesis, and allows for production of a wide variety of nitropyrazolones with high yields and purity. The synthesized compounds demonstrated high fungicidal activity against the broad spectrum of phytopathogenic fungi (Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum). Their mycelium growth inhibiting activity was comparable or superior to that of kresoximmethyl. In vitro activity against Staphyloccocus aureus, Candida albicans, and Aspergillus niger revealed that nitropyrazolones are promising candidates against human pathogens. The key factors for the manifestation of high fungicidal activity were established to be an aromatic substituent on the N1 atom and small substituents, such as methyl, at the C3 and C4 positions of the pyrazolone ring.

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