Microwave-assisted synthesis and biological evaluation of carbazole-based chalcones, aurones and flavones

被引:33
作者
Ashok, D. [1 ]
Ravi, S. [1 ]
Ganesh, Arram [1 ]
Lakshmi, B. Vijaya [1 ]
Adam, Shaik [2 ]
Murthy, S. D. S. [2 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, Andhra Pradesh, India
[2] Sri Venkateswara Univ, Dept Biochem, Tirupati 517502, Andhra Pradesh, India
关键词
Antimicrobial activity; Antioxidant activity; Carbazole Chalcones; Aurones; Flavones; Microwave irradiation; DERIVATIVES; DISCOVERY;
D O I
10.1007/s00044-016-1537-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A new class of chalcones, aurones and flavones derived from carbazole is designed as potential antimicrobial and antioxidant agents. Synthesis of (Z)-2-((9-ethyl-9H-carbazol-3-yl)methylene)benzofuran-3(2H)-ones and 2-(9-ethyl-9H-carbazol-3-yl)-4H-chromen-4-ones was carried out by the oxidation of (E)-3-(9-ethyl-9H-carbazol-3-yl)-1-(2-hydroxyphenyl)prop-2-en-1-ones under microwave irradiation and conventional heating. All the newly synthesized compounds were characterized on the basis of IR, H-1 NMR, C-13 NMR, mass and analytical data. All the synthesized compounds were evaluated for their antibacterial, antifungal and antioxidant activities. Synthesized compounds were screened in vitro for antibacterial activity against two gram-positive bacterial strains like Staphylococcus aureus and Bacillus subtilis and two gram-negative bacterial strains like Escherichia coli and Klebsiella pneumonia and antifungal activity by inhibitory action against three fungal strains like Fusarium oxysporum, Aspergillus niger and Aspergillus flavus. The synthesized compounds were also evaluated for their DPPH radical scavenging activity. All the newly synthesized compounds have shown good antibacterial, antifungal and antioxidant activities.
引用
收藏
页码:909 / 922
页数:14
相关论文
共 25 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, 2013, INDIAN J HETEROCY CH, V23, P11
[3]   Synthesis of some novel chalcones, flavanones and flavones and evaluation of their anti-inflammatory activity [J].
Bano, Sameena ;
Javed, Kalim ;
Ahmad, Shamim ;
Rathish, I. G. ;
Singh, Surender ;
Chaitanya, M. ;
Arunasree, K. M. ;
Alam, M. S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 65 :51-59
[4]   Design, synthesis and antileishmanial in vitro activity of new series of chalcones-like compounds: A molecular hybridization approach [J].
Barbosa, Ticiano P. ;
Sousa, Suervy C. O. ;
Amorim, Francianne M. ;
Rodrigues, Yara K. S. ;
de Assis, Priscilla A. C. ;
Caldas, John P. A. ;
Oliveira, Marcia R. ;
Vasconcellos, Mario L. A. A. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (14) :4250-4256
[5]   Antimitotic and antiproliferative activities of chalcones: Forward structure-activity relationship [J].
Boumendjel, Ahcene ;
Boccard, Juien ;
Carrupt, Pierre-Alain ;
Nicolle, Edwige ;
Blanc, Madeleine ;
Geze, Annabelle ;
Choisnard, Luc ;
Wouessidjewe, Denis ;
Matera, Eva-Laure ;
Dumontet, Charles .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (07) :2307-2310
[6]   Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb [J].
Chen, Zhuo ;
Liu, Yu-Mei ;
Yang, Song ;
Song, Bao-An ;
Xu, Guang-Fang ;
Bhadury, Pinaki S. ;
Jin, Lin-Hong ;
Hu, De-Yu ;
Liu, Fang ;
Xue, Wei ;
Zhou, Xia .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (03) :1337-1344
[7]   Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines [J].
Cheng, Huimin ;
Zhang, Lianwen ;
Liu, Yingxue ;
Chen, Shaopeng ;
Cheng, Hao ;
Lu, Xin ;
Zheng, Zhuxia ;
Zhou, Guo-Chun .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) :5950-5957
[8]   Antioxidant properties of hydroxy-flavones [J].
Cotelle, N ;
Bernier, JL ;
Catteau, JP ;
Pommery, J ;
Wallet, JC ;
Gaydou, EM .
FREE RADICAL BIOLOGY AND MEDICINE, 1996, 20 (01) :35-43
[9]  
de Groot H, 1998, FUND CLIN PHARMACOL, V12, P249
[10]   Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity [J].
Detsi, Anastasia ;
Majdalani, Maya ;
Kontogiorgis, Christos A. ;
Hadjipavlou-Litina, Dimitra ;
Kefalas, Panagiotis .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (23) :8073-8085