Schiff’s bases of quinazolinone derivatives: Synthesis and SAR studies of a novel series of potential anti-inflammatory and antioxidants

[Display omitted] A series of quinazolinone derived Schiff base derivatives 7–28 were synthesized and characterized as novel antioxidants and anti-inflammatory agents. The in vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidants ascorbic acid (AA),...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2015-03, Vol.25 (5), p.1072-1077
Main Authors: Rakesh, K.P., Manukumar, H.M., Gowda, D. Channe
Format: Article
Language:English
Subjects:
Anti-inflammatory activity
Anti-Inflammatory Agents - chemistry
Anti-Inflammatory Agents - pharmacology
Antioxidants
Antioxidants - chemistry
Antioxidants - pharmacology
Electronic effect
Humans
Quinazolinones
Quinazolinones - chemistry
Quinazolinones - pharmacology
Schiff Bases - chemistry
Schiff Bases - pharmacology
Schiff’s bases
Structure-Activity Relationship
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Summary:[Display omitted] A series of quinazolinone derived Schiff base derivatives 7–28 were synthesized and characterized as novel antioxidants and anti-inflammatory agents. The in vitro antioxidant activities of these compounds were evaluated and compared with commercial antioxidants ascorbic acid (AA), gallic acid (GA), butylatedhydroxytoluene (BHT), butylatedhydroxyanisole (BHA) employing 1,1-diphenyl-2-picryl-hydrazyl (DPPH) assay, 2,2-azinobis-(3-ethylbenzothiazoline-6-sufonic acid) (ABTS) assay and N,N-dimethyl-p-phenylenediamine dihydrochloride (DMPD) assay. The results revealed that IC50 of 17, 18, 23, 24, 25, 27 and 28 were lower than the IC50 of standards in all the three performed antioxidant assays indicating good activities of these compounds. In addition, in vitro anti-inflammatory activity of the synthesized compounds were evaluated and the results demonstrate that the compounds 9–12 exhibited excellent anti-inflammatory activity. Preliminary structure–activity relationship revealed that the compounds 17, 18, 23, 24, 25, 27 and 28 with electron donating moiety (OH, OCH3) were found to be excellent antioxidants and compounds 9, 10, 11 and 12 with electron withdrawing moiety (Cl, NO2) were found to be excellent anti-inflammatory agents.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2015.01.010