One-pot synthesis of carbazole based 3-hydroxy-4H-chromen-4-ones by a modified Algar-Flynn-Oyamada reaction and their antimicrobial activity

被引:5
作者
Ashok, Dongamanti [1 ]
Ravi, Sidda [1 ]
Lakshmi, Bommidi Vijaya [1 ]
Ganesh, Arram [1 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
2-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-4H-chromen-4-ones; modified Algar-Flynn-Oyamada reaction; antimicrobial activity; MICROWAVE-ASSISTED SYNTHESIS; FLAVONOIDS; AGENTS;
D O I
10.2298/JSC141203051A
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new series of 2-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-4H-chromen-4-ones were synthesized from substituted 2-hydroxyacetophenones and 9-ethyl-9H-carbazole-3-carbaldehyde using NaOH and H2O2 by a modified Algar-Flynn-Oyamada reaction. In this method, the flavonols were synthesized in good yields (70-82 %) without isolating chalcones. The structures of the compounds were established based on H-1-NMR, C-13-NMR, FT-IR and mass spectral and analytical data. All the compounds were evaluated for their antimicrobial activity against bacteria, such as Staphylococus aureus, Bacillus subtilis, Escherichia coli and Klebsiella pneumoniae, as well as fungi, such as Aspergillus flavus and Fusarium oxysporum.
引用
收藏
页码:1361 / +
页数:9
相关论文
共 15 条
[1]   Microwave-assisted synthesis of novel 1,2,3-triazole derivatives and their antimicrobial activity [J].
Ashok, D. ;
Gandhi, D. Mohan ;
Srinivas, G. ;
Kumar, A. Vikas .
MEDICINAL CHEMISTRY RESEARCH, 2014, 23 (06) :3005-3018
[2]  
Ashok D., 2015, MED CHEM RES, V84, P2234
[3]   Synthesis of novel carbazole chalcones as radical scavenger, antimicrobial and cancer chemopreventive agents [J].
Bandgar, Babasaheb P. ;
Adsul, Laxman K. ;
Lonikar, Shrikant V. ;
Chavan, Hemant V. ;
Shringare, Sadanand N. ;
Patil, Sachin A. ;
Jalde, Shivkumar S. ;
Koti, Basawaraj A. ;
Dhole, Nagesh A. ;
Gacche, Rajesh N. ;
Shirfule, Amol .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2013, 28 (03) :593-600
[4]   Antibacterial, Antiviral, and Antifungal Properties of Wines and Winery Byproducts in Relation to Their Flavonoid Content [J].
Friedman, Mendel .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (26) :6025-6042
[5]   Flavonoids as Anticancer Agents: Recent Progress and State of the Art? [J].
Genoux, Estelle ;
Nicolle, Edwige ;
Boumendjel, Ahcene .
CURRENT ORGANIC CHEMISTRY, 2011, 15 (15) :2608-2615
[6]  
Girish D. H., 2014, MED CHEM RES, V23, P461
[7]   Synthesis, structure, electrochemical properties, cytotoxic effects and antioxidant activity of 5-amino-8-methyl-4H-benzopyran-4-one and its copper(II) complexes [J].
Grazul, Magdalena ;
Kufelnicki, Aleksander ;
Wozniczka, Magdalena ;
Lorenz, Ingo-Peter ;
Mayer, Peter ;
Jozwiak, Andrzej ;
Czyz, Malgorzata ;
Budzisz, Elzbieta .
POLYHEDRON, 2012, 31 (01) :150-158
[8]   Synthesis of hetero annulated carbazoles: exploration of in vitro cytotoxicity and molecular docking studies [J].
Indumathi, Thangavel ;
Muthusankar, Aathi ;
Shanmughavel, P. ;
Prasad, K. J. Rajendra .
MEDCHEMCOMM, 2013, 4 (02) :450-455
[9]  
Kim H. P., 1996, NAT PROD SCI, V2, P1
[10]  
Meltzer EO, 2005, ALLERGY ASTHMA PROC, V26, P445