Design, synthesis, characterization and anti-inflammatory evaluation of novel pyrazole amalgamated flavones

Chavan, Hemant V.; Bandgar, B. P.; Adsul, Laxman K.; Dhakane, Valmik D.; Bhale, Pravin S.; Thakare, Vishnu N.; Masand, Vijay H.

doi:10.1016/j.bmcl.2012.12.094

Cited by 43 publications

(23 citation statements)

References 27 publications

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“…The cyclization of 6 into the corresponding biflavone 7 was initially attempted by using a catalytic amount of iodine in DMSO at 130–140 °C, conditions often used for the oxidative cyclization of chalcones to flavones [25]. However, at this temperature, the reaction resulted in decomposition of the starting material.…”

Section: Resultsmentioning

confidence: 99%

Total synthesis of ochnaflavone

Ndoile

Heerden

2013

Beilstein J. Org. Chem.

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SummaryThe first total syntheses of ochnaflavone, an asymmetric biflavone consisting of apigenin and luteolin moieties, and the permethyl ether of 2,3,2'',3''-tetrahydroochnaflavone have been achieved. The key steps in the synthesis of ochnaflavone were the formation of a diaryl ether and ring cyclization of an ether-linked dimeric chalcone to assemble the two flavone nuclei. Optimal experimental conditions for the oxidative cyclization to form ochnaflavone were established.

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Section: Resultsmentioning

confidence: 99%

Total synthesis of ochnaflavone

Ndoile

Heerden

2013

Beilstein J. Org. Chem.

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“…These predictions encouraged us to synthesize hybrid compounds containing arylpyrazole combined with chalcone scaffold. Based on the earlier findings and in continuation of our interest in the synthesis of novel bioactive molecules with potential anti-inflammatory activities [38][39][40][41] , a new series of pyrazolyl chalcones (10a-n) have been synthesized and evaluated for their anti-inflammatory potential.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

Chavan

Adsul

Kotmale

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.

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“…The synthesized pyrazole derivatives increased inhibition of paw edema formation at 6 h to a higher degree than inhibition of COX-2 [44]. Another study conducted by our group showed that the pyrazole derivative FPPT reduced edema formation as well as the leukocyte content in carrageenan-induced paw edema and pleurisy with similar doses used in this study in rats [45].…”

Section: Discussionmentioning

confidence: 55%

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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Design, synthesis, characterization and anti-inflammatory evaluation of novel pyrazole amalgamated flavones

Cited by 43 publications

References 27 publications

Total synthesis of ochnaflavone

Total synthesis of ochnaflavone

Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

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

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