- Design, synthesis, characterization and in vitro and in vivo anti-inflammatory evaluation of novel pyrazole-based chalcones
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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 1H-1H COSY, 1H-13C HSQC and 1H-13C HMBC experiments. 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.
- Chavan, Hemant V.,Adsul, Laxman K.,Kotmale, Amol S.,Dhakane, Valmik D.,Thakare, Vishnu N.,Bandgar, Babasaheb P.
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- Design, synthesis, characterization and anti-inflammatory evaluation of novel pyrazole amalgamated flavones
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A series of novel pyrazole amalgamated flavones has been designed and synthesized from 1-methyl-5-(2,4,6-trimethoxy-phenyl)-1H-pyrazole 6. The structures of regioisomers 6 and 7 were resolved by 2D 1H- 1H COSY, 1H-13C HSQC and 1H- 13C HMBC experiments. The newly synthesized compounds were tested for their in vitro COX inhibition and in vivo carrageenan induced hind paw edema in rats and acetic acid induced vascular permeability in mice. Although the compounds have inhibitory profile against both COX-1 and COX-2, some of the compounds are found to be selective against COX-2, supported by inhibition of paw edema and vascular permeability. Docking studies were also carried out to determine the structural features which sway the anti-inflammatory activity of the tested compounds. The keto and phenolic -OH are major factors that are prominently involved in interaction with COX-2 active site.
- Chavan, Hemant V.,Bandgar, Babasaheb P.,Adsul, Laxman K.,Dhakane, Valmik D.,Bhale, Pravin S.,Thakare, Vishnu N.,Masand, Vijay
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p. 1315 - 1321
(2013/03/14)
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