Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeutics
Two series of quinazolinone derived Schiff's bases were synthesized and characterized by analytical and spectroscopic techniques. All the compounds were screened for their in vitro biological studies. The in vitro antioxidant activities of these compounds were evaluated employing 1,1-diphenyl-2...
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doaj-f2efe599655e47799fe775b4815e8a9d2020-12-29T04:14:16ZengElsevierResults in Chemistry2211-71562020-01-012100067Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeuticsB.J. Ullas0K.P. Rakesh1J. Shivakumar2D. Channe Gowda3P.G. Chandrashekara4Department of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, Karnataka, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, Karnataka, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, Karnataka, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, Karnataka, IndiaDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, Karnataka, India; Corresponding author.Two series of quinazolinone derived Schiff's bases were synthesized and characterized by analytical and spectroscopic techniques. All the compounds were screened for their in vitro biological studies. The in vitro antioxidant activities of these compounds were evaluated employing 1,1-diphenyl-2-picryl-hydrazyl (DPPH), 2,2-azinobis-(3-ethylbenzothiazoline-6-sufonic acid) (ABTS+) and N,N-dimethyl-p-phenylenediamine dihydrochloride (DMPD+) radical assay. The results revealed that compounds 31 (IC50: 35 μg/mL) and 32 (IC50: 40 μg/mL) showed excellent antioxidant activity and their IC50 is lower than the IC50 of standards such as butylated hydroxyl anisole, ascorbic acid and gallic acid in all the three performed assays. In anti-inflammatory activity, compounds 7–26 (IC50: 10-35 μg/mL) showed extraordinary activity compared to standards indomethacin (IC50: 40 μg/mL) and ibuprofen (IC50: 65 μg/mL). In antimicrobial activity, compounds 25–42 shows potent antibacterial activity and compounds 25–42 shows potent antifungal activity compared to standards streptomycin (ZoI: 10 mm) and bavistin (ZoI:10 mm) respectively. To study the structure activity relationship (SAR), electron donating groups (-OH and -OCH3) favors the antioxidant activity, electron withdrawing groups (F, Cl, Br and -NO2) favors the anti-inflammatory activity, and both electron donating (-OH and -OCH3) and electron withdrawing (F, Cl, Br and -NO2) groups (25–32) or heterocyclic moiety (33–42) favors antimicrobial activity.http://www.sciencedirect.com/science/article/pii/S221171562030045XQuinazolinoneSchiff's basesAntioxidantAnti-inflammatoryAntimicrobial |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
B.J. Ullas K.P. Rakesh J. Shivakumar D. Channe Gowda P.G. Chandrashekara |
spellingShingle |
B.J. Ullas K.P. Rakesh J. Shivakumar D. Channe Gowda P.G. Chandrashekara Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeutics Results in Chemistry Quinazolinone Schiff's bases Antioxidant Anti-inflammatory Antimicrobial |
author_facet |
B.J. Ullas K.P. Rakesh J. Shivakumar D. Channe Gowda P.G. Chandrashekara |
author_sort |
B.J. Ullas |
title |
Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeutics |
title_short |
Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeutics |
title_full |
Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeutics |
title_fullStr |
Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeutics |
title_full_unstemmed |
Multi-targeted quinazolinone-Schiff's bases as potent bio-therapeutics |
title_sort |
multi-targeted quinazolinone-schiff's bases as potent bio-therapeutics |
publisher |
Elsevier |
series |
Results in Chemistry |
issn |
2211-7156 |
publishDate |
2020-01-01 |
description |
Two series of quinazolinone derived Schiff's bases were synthesized and characterized by analytical and spectroscopic techniques. All the compounds were screened for their in vitro biological studies. The in vitro antioxidant activities of these compounds were evaluated employing 1,1-diphenyl-2-picryl-hydrazyl (DPPH), 2,2-azinobis-(3-ethylbenzothiazoline-6-sufonic acid) (ABTS+) and N,N-dimethyl-p-phenylenediamine dihydrochloride (DMPD+) radical assay. The results revealed that compounds 31 (IC50: 35 μg/mL) and 32 (IC50: 40 μg/mL) showed excellent antioxidant activity and their IC50 is lower than the IC50 of standards such as butylated hydroxyl anisole, ascorbic acid and gallic acid in all the three performed assays. In anti-inflammatory activity, compounds 7–26 (IC50: 10-35 μg/mL) showed extraordinary activity compared to standards indomethacin (IC50: 40 μg/mL) and ibuprofen (IC50: 65 μg/mL). In antimicrobial activity, compounds 25–42 shows potent antibacterial activity and compounds 25–42 shows potent antifungal activity compared to standards streptomycin (ZoI: 10 mm) and bavistin (ZoI:10 mm) respectively. To study the structure activity relationship (SAR), electron donating groups (-OH and -OCH3) favors the antioxidant activity, electron withdrawing groups (F, Cl, Br and -NO2) favors the anti-inflammatory activity, and both electron donating (-OH and -OCH3) and electron withdrawing (F, Cl, Br and -NO2) groups (25–32) or heterocyclic moiety (33–42) favors antimicrobial activity. |
topic |
Quinazolinone Schiff's bases Antioxidant Anti-inflammatory Antimicrobial |
url |
http://www.sciencedirect.com/science/article/pii/S221171562030045X |
work_keys_str_mv |
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