Recent advanced in bioactive systems containing pyrazole fused with a five membered heterocycle

Raffa, Demetrio; Maggio, Benedetta; Raimondi, Maria Valeria; Cascioferro, Stella; Plescia, Fulvio; Cancemi, Gabriella; Daidone, Giuseppe

doi:10.1016/j.ejmech.2014.12.023

Cited by 115 publications

(41 citation statements)

References 22 publications

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“…These heterocyclic compounds can be seen in nature as alkaloids, vitamins, pigments and constituents of plant and animal cells widely 12 . Medicinal chemists have great attention of pyrazolines and substituted pyrazolines because of their various biological activities such as antimicrobial, anticonvulsant, anticancer, anti-inflammatory, antitubercular, antiviral, analgesic and antidepressive activities [13][14][15][16][17] . Sulfonamide is an important functional group in medicinal chemistry having a wide range of bioactivities such as cytotoxic, carbonic anhydrase inhibitory, antibacterial, antimalarial, antihypertensive, antiviral, anti-inflammatory and diuretics activities 8,13,[18][19][20][21][22][23][24][25] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Küçükoğlu

Oral

Aydin

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of polymethoxylated-pyrazoline benzene sulfonamides were synthesized, investigated for their cytotoxic activities on tumor and non-tumor cell lines and inhibitory effects on carbonic anhydrase isoenzymes (hCA I and hCA II). Although tumor selectivity (TS) of the compounds were less than the reference compounds 5-Fluorouracil and Melphalan, trimethoxy derivatives 4, 5, and 6 were more selective than dimethoxy derivatives 2 and 3 as judged by the cytotoxicity assay with the cells both types originated from the gingival tissue. The compound 6 (4-[3-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl] benzene sulfonamide) showed the highest TS values and can be considered as a lead molecule of the series for further investigations. All compounds synthesized showed superior CA inhibitory activity than the reference compound acetazolamide on hCA I, and II isoenzymes, with inhibition constants in the range of 26.5-55.5 nM against hCA I and of 18.9-28.8 nM against hCA II, respectively.

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Section: Introductionmentioning

confidence: 99%

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Küçükoğlu

Oral

Aydin

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Pentatomic nitrogenous heterocyclic compounds are widely described in the literature for a variety of biological activities [43][44][45] including the antibacterial activity [46][47][48]. This observation, combined with the interesting biological results observed with the natural pyrrolomycins, encouraged the synthesis of new analogs.…”

Section: Synthetic Pyrrolomycinsmentioning

confidence: 99%

Pharmaceutical Potential of Synthetic and Natural Pyrrolomycins

et al. 2015

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Abstract:The emergence of antibiotic resistance is currently considered one of the most important global health problem. The continuous onset of multidrug-resistant Gram-positive and Gram-negative bacterial strains limits the clinical efficacy of most of the marketed antibiotics. Therefore, there is an urgent need for new antibiotics. Pyrrolomycins are a class of biologically active compounds that exhibit a broad spectrum of biological activities, including antibacterial, antifungal, anthelmintic, antiproliferative, insecticidal, and acaricidal activities. In this review we focus on the antibacterial activity and antibiofilm activity of pyrrolomycins against Gram-positive and Gram-negative pathogens. Their efficacy, combined in some cases with a low toxicity, confers to these molecules a great potential for the development of new antimicrobial agents to face the antibiotic crisis.

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“…The pyrazole ring, bearing atoms of at least two different elements as a member of its ring, is considered to be a privileged structure and an attractive scaffold for drug discovery [10,11]. Pyrazole derivatives represent one of the most active classes of compounds and exhibit a broad spectrum of pharmacological activities, such as antimicrobial [12,13], analgesic [14,15], anti-inflammatory [16e18], antipyretic [15,19], cardiovascular [20] and anticancer [21,22] activities, among others effects.…”

Section: Introductionmentioning

confidence: 99%

Potential anti-inflammatory effect of LQFM-021 in carrageenan-induced inflammation: The role of nitric oxide

Florentino

Silva

et al. 2017

Nitric Oxide

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The pyrazole compound LQFM-021 exhibits vasorelaxant, antinociceptive and anti-inflammatory activities. Furthermore, it has low toxicity, indicating that this compound may be considered to be a good prototype for the development of new analgesic/anti-inflammatory drugs. Therefore, the aim of this study was to investigate the potential anti-inflammatory activity of LQFM-021 using a model of carrageenan-induced inflammation as well as the mechanism of action and role of nitric oxide in this effect. Acute treatments with LQFM-021 (30 and 60 mg/kg p.o.) reduced paw edema formation dose-dependently 2 h after carrageenan injection. In the carrageenan-induced pleurisy test, LQFM-021 (30 mg/kg p.o.) reduced the leukocyte (polymorphonuclear) count in the pleural cavity, as well as decreased protein extravasation and myeloperoxidase activity. This dose of LQFM-021 increased the NO (nitrite/nitrate) and IL-4 levels and decreased the TNF-α and IL-1β levels in the pleural cavity. Moreover, pre-treatment with L-NAME reversed the effect of LQFM-021 on NO, leukocyte migration, and the TNF-α and IL-1β levels. Additionally, we observed that LQFM-021 showed weak inhibitory activity on cyclooxygenases, but reduced the PGE levels in the pleural cavity. Immunoblot analyses showed that LQFM-021 promoted a decrease in COX-2 levels and increase in iNOS levels. In conclusion, we demonstrated that LQFM-021 has marked anti-inflammatory activity by reducing polymorphonuclear recruitment, which is associated with the inhibition of the production of inflammatory cytokines and eicosanoids. In addition, we found that the synthase/release of nitric oxide promoted by LQFM-021 is essential for the anti-inflammatory effect observed.

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Recent advanced in bioactive systems containing pyrazole fused with a five membered heterocycle

Cited by 115 publications

References 22 publications

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Synthesis, cytotoxicity and carbonic anhydrase inhibitory activities of new pyrazolines

Pharmaceutical Potential of Synthetic and Natural Pyrrolomycins

Potential anti-inflammatory effect of LQFM-021 in carrageenan-induced inflammation: The role of nitric oxide

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