Facile Heterocyclic Synthesis and Antibacterial Activity of Substituted Isoxazol-5(4H)-ones

被引:18
作者
Ferouani, Ghaniya [1 ]
Nacer, Amina [1 ,2 ]
Ameur, Nawal [1 ,3 ]
Bachir, Redouane [1 ]
Ziani-Cherif, Chewki [1 ]
机构
[1] Univ Tlemcen, Lab Catalysis & Synth Organ Chem, BP 119, Tilimsen, Algeria
[2] Tech & Sci Res Ctr Physicochem Anal, Bou Ismail, Tipaza, Algeria
[3] ESG2E, Oran, Algeria
关键词
3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones; One-pot synthesis; Aqueous media; Lithium bromide; Antimicrobial activity; KNOEVENAGEL CONDENSATION; LITHIUM BROMIDE; IN-VITRO; DERIVATIVES; EFFICIENT; MULTICOMPONENT; CATALYST; GREEN; INHIBITORS; ALDEHYDES;
D O I
10.1002/jccs.201700334
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient, simple, and green procedure for the synthesis of isoxazol-5(4H)-one derivatives are described here through a convenient one-pot, three-component reaction at room temperature. The title compounds are isolated in high to excellent yields and after short reaction times, and are characterized by various spectroscopic methods such as IR, H-1 NMR, and C-13 NMR. The synthesized compounds 4a-c and 4e-i were tested for their in vitro activity against a panel of Gram-positive and Gram-negative bacteria, demonstrating their ability to inhibit microorganisms with a zone of inhibition ranging from 15 to 30 mm, minimum inhibitory concentration between 250 and 900 g/mL, and minimum bacterial concentration between 700 and 1000 g/mL.
引用
收藏
页码:459 / 464
页数:6
相关论文
共 41 条
[1]  
Aaglawe M J., 2003, J KOR CHEM SOC, V2, P133, DOI [10.5012/jkcs.2003.47.2.133, DOI 10.5012/JKCS.2003.47.2.133]
[2]   A valuable heterocyclic ring transformation:: from isoxazolin-5(2H)-ones to quinolines [J].
Abbiati, G ;
Beccalli, EM ;
Broggini, G ;
Zoni, C .
TETRAHEDRON, 2003, 59 (50) :9887-9893
[3]   EFFICIENT ONE-POT SYNTHESIS OF β-UNSATURATED ISOXAZOL-5-ONES AND PYRAZOL-5-ONES UNDER ULTRASONIC IRRADIATION [J].
Ablajan, Keyume ;
Xiamuxi, Hainimu .
SYNTHETIC COMMUNICATIONS, 2012, 42 (08) :1128-1136
[4]   A family of substituted hydrazonoisoxazolones with potential biological properties [J].
Bustos, Carlos ;
Molins, Elies ;
Carcamo, Juan-Guillermo ;
Aguilar, Marcelo N. ;
Sanchez, Christian ;
Moreno-Villoslada, Ignacio ;
Nishide, Hiroyuki ;
Zarate, Ximena ;
Schott, Eduardo .
NEW JOURNAL OF CHEMISTRY, 2016, 40 (03) :2156-2167
[5]   Water as the reaction medium for multicomponent reactions based on boronic acids [J].
Candeias, Nuno R. ;
Cal, Pedro M. S. D. ;
Andre, Vania ;
Duarte, M. Teresa ;
Veiros, Luis F. ;
Gois, Pedro M. P. .
TETRAHEDRON, 2010, 66 (14) :2736-2745
[6]   Facile synthesis of active antitubercular, cytotoxic and antibacterial agents: a Michael addition approach [J].
Chande, MS ;
Verma, RS ;
Barve, PA ;
Khanwelkar, RR ;
Vaidya, RB ;
Ajaikumar, KB .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (11) :1143-1148
[7]  
Clark M. P., 2005, CHEMINFORM, V36, P2399
[8]   STRUCTURE OF ACYL DERIVATIVES OF FUNGICIDE DRAZOXOLON AND RELATED ARYLHYDRAZONOISOXAZOLONES [J].
ECKHARD, IF ;
LEHTONEN, K ;
STAUB, T ;
SUMMERS, LA .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1973, 26 (12) :2705-2710
[9]  
ERGENC N, 1993, PHARMAZIE, V48, P780
[10]   PARTIAL GABA(A) RECEPTOR AGONISTS - SYNTHESIS AND IN-VITRO PHARMACOLOGY OF A SERIES OF NONANNULATED ANALOGS OF 4,5,6,7-TETRAHYDROISOXAZOLO[5,4-C]PYRIDIN-3-OL [J].
FROLUND, B ;
KRISTIANSEN, U ;
BREHM, L ;
HANSEN, AB ;
KROGSGAARDLARSEN, P ;
FALCH, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (17) :3287-3296