Microwave-assisted one-pot synthesis of some new flavonols by modified Algar-Flynn-Oyamada reaction and their antimicrobial activity

被引:14
作者
Ashok, Dongamanti [1 ]
Kifah, Mohsin Ahmed [1 ]
Lakshmi, Bommidi Vijaya [1 ]
Sarasija, Madderla [2 ]
Adam, Shaik [3 ]
机构
[1] Osmania Univ, Dept Chem, Hyderabad 500007, Telangana, India
[2] Satavahana Univ, Dept Chem, Karimnagar 505001, Telangana, India
[3] ANGRAU, Reg Agr Res Stn, Tirupati 517502, Andhra Pradesh, India
关键词
3-hydroxy-2-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]-4H-chromen-4-ones; 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde; antimicrobial activity; microwave irradiation; modified Algar-Flynn-Oyamada reaction; BIOLOGICAL EVALUATION; PYRAZOLE; DERIVATIVES; DESIGN; SERIES;
D O I
10.1007/s10593-016-1852-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new series of 3-hydroxy-2-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]-4H-chromen-4-ones has been synthesized from substituted 2-hydroxyacetophenones and 1-phenyl-3-(thiophen-2-yl)-1H-pyrazole-4-carbaldehyde using NaOH and H2O2 by modified Algar-Flynn-Oyamada reaction under conventional and microwave irradiation conditions. In this method flavonols are synthesized without isolating chalcones in good yields (80-85%). The structures of the compounds were established on the basis of IR, H-1, C-13 NMR and mass spectral and elemental analysis data. The synthesized compounds were screened for their antibacterial and antifungal activities.
引用
收藏
页码:172 / 176
页数:5
相关论文
共 38 条
[1]  
Amr Abd El-Galil El-Sayed, 2006, Acta Pharmaceutica (Zagreb), V56, P203
[2]   Microwave-assisted synthesis of substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones and their antimicrobial activity [J].
Ashok, D. ;
Lakshmi, B. Vijaya ;
Ravi, S. ;
Ganesh, A. .
MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (04) :1487-1495
[3]   Microwave-assisted synthesis of some new coumarin-pyrazoline hybrids and their antimicrobial activity [J].
Ashok, Dongamanti ;
Lakshmi, Bommidi Vijaya ;
Ravi, Sidda ;
Ganesh, Arram .
JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2015, 80 (03) :305-313
[4]   Synthesis and biological evaluation of a novel series of 2,2-bisaminomethylated aurone analogues as anti-inflammatory and antimicrobial agents [J].
Bandgar, Babasaheb R. ;
Patil, Sachin A. ;
Korbad, Balaji L. ;
Biradar, Satish C. ;
Nile, Shivraj N. ;
Khobragade, Chandrahasya N. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (07) :3223-3227
[5]  
Bhuiyan Md. Mosharef Hossain, 2009, Pakistan Journal of Scientific and Industrial Research, V52, P180
[6]  
Blair B., 2011, PCT Int. Appl, Patent No. [WO 2011005674 A1 20110113, 2011005674]
[7]   Antibacterial, antifungal and cytotoxic properties of some sulfonamide-derived chromones [J].
Chohan, Zahid H. ;
Rauf, Abdul ;
Naseer, Muhammad M. ;
Somra, Muhammad A. ;
Supuran, Claudiu T. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2006, 21 (02) :173-177
[8]   Radical scavenging and xanthine oxidase inhibitory activity of phenolic compounds from Bridelia ferruginea stem bark [J].
Cimanga, K ;
Ying, L ;
De Bruyne, T ;
Apers, S ;
Cos, P ;
Hermans, N ;
Bakana, P ;
Tona, L ;
Kambu, K ;
Kalenda, DT ;
Pieters, L ;
Vanden Berghe, D ;
Vlietinck, AJ .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 2001, 53 (05) :757-761
[9]   Simultaneous determination of five pyrazole fungicides in cereals, vegetables and fruits using liquid chromatography/tandem mass spectrometry [J].
Dong, Fengshou ;
Chen, Xiu ;
Liu, Xingang ;
Xu, Jun ;
Li, Yuanbo ;
Shan, Weili ;
Zheng, Yongquan .
JOURNAL OF CHROMATOGRAPHY A, 2012, 1262 :98-106
[10]   A Novel COX-2 Inhibitor Pyrazole Derivative Proven Effective as an Anti-Inflammatory and Analgesic Drug [J].
El-Din, Mahmoud M. Mohy ;
Senbel, Amira M. ;
Bistawroos, Azza A. ;
El-Mallah, Ahmed ;
El-Din, Nour A. Nour ;
Bekhit, Adnan A. ;
Abd El Razik, Heba A. .
BASIC & CLINICAL PHARMACOLOGY & TOXICOLOGY, 2011, 108 (04) :263-273