Synthesis and evaluation of new phenolic derivatives as antimicrobial and antioxidant agents

被引:2
作者
Chaaban, Ibrahim [1 ]
El Khawass, El Sayeda M. [1 ]
Abd El Razik, Heba A. [1 ]
El Salamouni, Nehad S. [1 ]
Ghareeb, Doaa A. [2 ]
Wahab, Abeer E. Abdel [3 ]
机构
[1] Alexandria Univ, Dept Pharmaceut Chem, Fac Pharm, Alexandria 21521, Egypt
[2] Alexandria Univ, Dept Biochem, Fac Sci, Alexandria, Egypt
[3] Genet Engn & Biotechnol Res Inst GEBRI, Med Biotechnol Dept, City Sci Res & Technol Applicat, Alexandria, Egypt
来源
MONATSHEFTE FUR CHEMIE | 2018年 / 149卷 / 01期
关键词
Phenolic derivatives; Hydrazine; 1,3,4-Oxadiazole; Synthesis; Antimicrobial activity; Antioxidant activity; BIOLOGICAL EVALUATION; FREE-RADICALS; SCAVENGING ACTIVITY; OXIDATIVE STRESS; ANTICANCER; EXTRACTS; ANALOGS; MOIETY;
D O I
10.1007/s00706-017-1983-z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New phenolic derivatives bearing hydrazine and 1,3,4-oxadiazole moieties were synthesized and evaluated for their in vitro antimicrobial and antioxidant activities. Most of the compounds revealed pronounced activity against Pseudomonas aeruginosa as well as promising antioxidant activities. N (1)-(2,5-Dihydroxybenzoyl)-N (2)-(4-methylphenylsulfonyl)hydrazine displayed promising activity against Escherichia coli and P. aeruginosa. N (1)-(2,5-Dihydroxybenzoyl)-N (2)-(2-naphthalenylmethylene)hydrazine was almost equipotent to the standard antioxidant vitamin C having scavenging activities of 84 and 93%, respectively. In vitro cytotoxicity study revealed that N (1)-(2,5-dihydroxybenzoyl)-N (2)-(2,3,4-trimethoxyphenylmethylene)hydrazine, N (1)-(2,5-dihydroxybenzoyl)-N (2)-(3,4,5-trimethoxyphenylmethylene)hydrazine, and N (1)-(2,5-dihydroxybenzoyl)-N (2)-(4-methylphenylsulfonyl)hydrazine are more safe than reference 5-fluorouracil. In silico drug relevant properties proposed that all compounds have high to moderate drug-likeness scores. Accordingly, these derivatives can be potential leads for development of potent antimicrobial and antioxidant agents. [GRAPHICS]
引用
收藏
页码:127 / 139
页数:13
相关论文
共 47 条
[1]  
Arunkumar S., 2009, Int J ChemTech Res, V1, P1094
[2]   Free radicals, oxidative stress, and antioxidants in human health and disease [J].
Aruoma, OI .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1998, 75 (02) :199-212
[3]   Diazinium salts with dihydroxyacetophenone skeleton: Syntheses and antimicrobial activity [J].
Balan, Ana Maria ;
Florea, Ondina ;
Moldoveanu, Costel ;
Zbancioc, Gheorghita ;
Iurea, Dorina ;
Mangalagiu, Ionel I. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (05) :2275-2279
[4]   Synthesis and DPPH radical scavenging activity of novel compounds obtained from tyrosol and cinnamic acid derivatives [J].
Barontini, Maurizio ;
Bernini, Roberta ;
Carastro, Isabella ;
Gentili, Patrizia ;
Romani, Annalisa .
NEW JOURNAL OF CHEMISTRY, 2014, 38 (02) :809-816
[5]   THE ANTIOXIDANT ROLE OF VITAMIN-C [J].
BENDICH, A ;
MACHLIN, LJ ;
SCANDURRA, O ;
BURTON, GW ;
WAYNER, DDM .
ADVANCES IN FREE RADICAL BIOLOGY AND MEDICINE, 1986, 2 (02) :419-444
[6]   ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL [J].
BLOIS, MS .
NATURE, 1958, 181 (4617) :1199-1200
[7]  
Borenfreund E., 1985, J Tissue Cult Methods, V9, P7, DOI DOI 10.1007/BF01666038
[8]  
BOYUM A, 1968, SCAND J CLIN LAB INV, VS 21, P77
[9]  
CHAABAN I, 1980, Scientia Pharmaceutica, V48, P356
[10]   Synthesis and Anti-Proliferative Activity of Sulfanyltriazolylnaphthalenols and Sulfanyltriazolylnaphthalene-1,4-diones [J].
Chaaban, Ibrahim ;
El Khawass, El Sayeda M. ;
Abd El Razik, Heba A. ;
El Salamouni, Nehad S. ;
Redondo-Horcajo, Mariano ;
Barasoain, Isabel ;
Fernando Diaz, Jose ;
Yli-Kauhaluoma, Jari ;
Moreira, Vania M. .
ARCHIV DER PHARMAZIE, 2016, 349 (09) :749-761