Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents

被引:89
作者
Alshibl, Hanan M. [1 ]
Al-Abdullah, Ebtehal S. [1 ]
Haiba, Mogedda E. [1 ,2 ]
Alkahtani, Hamad M. [1 ]
Awad, Ghada E. A. [3 ]
Mahmoud, Ahlam H. [4 ]
Ibrahim, Bassant M. M. [5 ]
Bari, Ahmed [1 ]
Villinger, Alexander [6 ]
机构
[1] King Saud Univ, Dept Pharmaceut Chem, Coll Pharm, Riyadh 11451, Saudi Arabia
[2] Natl Res Ctr, Dept Med Chem, Cairo 12622, Egypt
[3] Natl Res Ctr, Chem Nat & Microbial Prod Dept, Cairo 12622, Egypt
[4] Natl Res Ctr, Pharmaceut & Drug Ind Res Div, Dept Therapeut Chem, Cairo 12622, Egypt
[5] Natl Res Ctr, Div Med Res, Dept Pharmacol, Cairo 12622, Egypt
[6] Univ Rostock, Abt Anorgan Chem, Inst Chem, Albert Einstein Str 3a, D-18059 Rostock, Germany
关键词
anti-inflammatory; antioxidant; antimicrobial; coumarin; sulfonamide; pyranocoumarin; synthesis; CLINICAL-USE; ANTIBACTERIAL; PHARMACOLOGY; TOXICITY; BINDING;
D O I
10.3390/molecules25143251
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
New pyranocoumarin and coumarin-sulfonamide derivatives were prepared and evaluated for their antioxidant, antimicrobial, and/or anti-inflammatory activities. Coumarin-sulfonamide compounds8a-ddemonstrated significant antioxidant activity, while7c,d,8c,d, and9c,dexhibited antimicrobial activity equal to or higher than the standard antimicrobials against at least one tested microorganism. Regarding the anti-inflammatory testing, pyranocoumarins2b,3a,band5cand coumarin-sulfonamide compound9ashowed more potent antiproteinase activity than aspirin in vitro; however, five compounds were as potent as aspirin. The anti-inflammatory activity of the promising compounds was further assessed pharmacologically on formaldehyde-induced rat paw oedema and showed significant inhibition of oedema. For in vitro COX-inhibitory activity of coumarin derivatives, pyranocoumarin derivative5awas the most selective (SI = 152) and coumarin-sulfonamide derivative8dwas most active toward COX-2 isozyme. The most active derivatives met the in silico criteria for orally active drugs; thus, they may serve as promising candidates to develop more potent and highly efficient antioxidant, antimicrobial, and/or anti-inflammatory agents.
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页数:28
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