Synthesis and biological evaluation of novel quinolin-2(1H)-one derivatives as potential antimicrobial agents

被引:8
作者
Deng, Qiao [1 ]
Ji, Qing-Gang [1 ]
Ge, Zhi-Qiang [1 ]
Liu, Xiao-Fei [1 ]
Yang, Dan [1 ]
Yuan, Lv-Jiang [1 ]
机构
[1] Southwest Univ, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China
关键词
Quinolin-2(1H)-one; L-Alanine ester; Amide; Antibacterial; Antifungal; BAD BUGS; CHALLENGES; DRUGS;
D O I
10.1007/s00044-014-1107-9
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of novel quinolin-2(1H)-one derivatives were synthesized and characterized by IR, H-1 NMR, C-13 NMR, and MS spectral data. All the new compounds were screened for their antimicrobial activities against six trains of bacteria and five fungi in vitro by twofold serial dilution technique. The bioactive assay showed that most of the compounds exhibited moderate to good antimicrobial activities in comparison with the streptomycin, especially, compound 6a, the fluoro-substituted aromatic amide derivative, showed good antibacterial activities against B.proteus and P.aeruginosa with minimal inhibitory concentration value of 32 and 16 mu g/ml, respectively.
引用
收藏
页码:5224 / 5236
页数:13
相关论文
共 30 条
[1]   Streamlined processes for the synthesis of a farnesyl transferase inhibitor drug candidate [J].
Andresen, BM ;
Couturier, M ;
Cronin, B ;
D'Occhio, M ;
Ewing, MD ;
Guinn, M ;
Hawkins, JM ;
Jasys, VJ ;
LaGreca, SD ;
Lyssikatos, JP ;
Moraski, G ;
Ng, K ;
Raggon, JW ;
Stewart, AM ;
Tickner, DL ;
Tucker, JL ;
Urban, FJ ;
Vazquez, E ;
Wei, LL .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (04) :643-650
[2]   Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities [J].
Bayrak, Hacer ;
Demirbas, Ahmet ;
Karaoglu, Senguel Alpay ;
Demirbas, Neslihan .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (03) :1057-1066
[3]   Synthesis and anti-inflammatory activity of N-substituted 2-oxo-2H-1-benzopyran-3-carboxamides and their 2-iminoanalogues [J].
Bylov, IE ;
Vasylyev, MV ;
Bilokin, YV .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1999, 34 (11) :997-1001
[4]   One-pot reductive mono-N-alkylation of aniline and nitroarene derivatives using aldehydes [J].
Byun, Eunyoung ;
Hong, Bomi ;
De Castro, Kathlia A. ;
Lim, Minkyung ;
Rhee, Hakjune .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (25) :9815-9817
[5]   Anticancer and antifungal activity of copper(II) complexes of quinolin-2(1H)-one-derived Schiff bases [J].
Creaven, Bernadette S. ;
Duff, Brian ;
Egan, Denise A. ;
Kavanagh, Kevin ;
Rosair, Georgina ;
Thangella, Venkat Reddy ;
Walsh, Maureen .
INORGANICA CHIMICA ACTA, 2010, 363 (14) :4048-4058
[6]   Quinolin-2(1H)-one-triazole derived Schiff bases and their Cu(II) and Zn(II) complexes: possible new therapeutic agents [J].
Creaven, Bernadette S. ;
Devereux, Michael ;
Foltyn, Agnieszka ;
McClean, Siobhan ;
Rosair, Georgina ;
Thangella, Venkat Reddy ;
Walsh, Maureen .
POLYHEDRON, 2010, 29 (02) :813-822
[7]   Endochin Optimization: Structure-Activity and Structure-Property Relationship Studies of 3-Substituted 2-Methyl-4(1H)-quinolones with Antimalarial Activity [J].
Cross, R. Matthew ;
Monastyrskyi, Andrii ;
Mukta, Tina S. ;
Burrows, Jeremy N. ;
Kyle, Dennis E. ;
Manetsch, Roman .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :7076-7094
[8]   ENANTIOMERS OF 1-ETHYL-7-[3-[(ETHYLAMINO)METHYL]-1-PYRROLIDINYL]-6,8-DIFLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINE-CARBOXYLIC ACID - PREPARATION AND BIOLOGICAL-ACTIVITY [J].
CULBERTSON, TP ;
DOMAGALA, JM ;
NICHOLS, JB ;
PRIEBE, S ;
SKEEAN, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1711-1715
[9]   Synthesis and antimalarial activity of new 4-amino-7-chloroquinolyl amides, sulfonamides, ureas and thioureas [J].
Ekoue-Kovi, Kekeli ;
Yearick, Kimberly ;
Iwaniuk, Daniel P. ;
Natarajan, Jayakumar K. ;
Alumasa, John ;
de Dios, Angel C. ;
Roepe, Paul D. ;
Wolf, Christian .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (01) :270-283
[10]   Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides [J].
El Akri, Khalid ;
Bougrin, Khalid ;
Balzarini, Jan ;
Faraj, Abdesslem ;
Benhida, Rachid .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (23) :6656-6659