A FACILE ONE-STEP MULTI-COMPONENT APPROACH TOWARD THE SYNTHESIS OF 3-(2-AMINO-4-THIAZOLYL) COUMARINS BY USING TRIMETHYLSILYL ISOTHIOCYANATE AND THEIR ANTIOXIDANT AND ANTI-INFLAMMATORY ACTIVITY

被引:12
作者
Ramagiri, Raj Kumar [1 ]
Vedula, Rajeswar Rao [1 ]
Thupurani, Murali Krishna [2 ]
机构
[1] Natl Inst Technol, Dept Chem, Warangal 506004, Andhra Pradesh, India
[2] Chaithanya Postgrad Coll Autonomous, Dept Biotechnol, Hanamkonda, Andhra Pradesh, India
关键词
Trimethylsilyl isothiocyanate; coumarin; multi-component reaction; primary amines; REAGENT;
D O I
10.1080/10426507.2014.990016
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A multi-component synthesis of 3-(2-amino-4-thiazolyl)coumarins has been reported from 3-(2-bromoacetyl)-2H-chromen-2-ones primary amines and using commercially available trimethylsilyl isothiocyanate. The structures of newly synthesized compounds were characterized by their analytical and spectral data. All the title compounds were screened for antioxidant and anti-inflammatory activity. Among the screened compounds, 4b exhibited highest free radical scavenging activity and also 4b was found to be effective in inhibiting the protein denaturation at all tested concentrations.
引用
收藏
页码:1393 / 1397
页数:5
相关论文
共 28 条
[1]  
Anklekar KY, 2003, INDIAN J CHEM B, V42, P1548
[2]   Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents [J].
Argyropoulou, Iro ;
Geronikaki, Athina ;
Vicini, Paola ;
Zani, Franca .
ARKIVOC, 2009, :89-102
[3]   Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling [J].
Bach, T ;
Heuser, S .
TETRAHEDRON LETTERS, 2000, 41 (11) :1707-1710
[4]   ANTIOXIDANT DETERMINATIONS BY THE USE OF A STABLE FREE RADICAL [J].
BLOIS, MS .
NATURE, 1958, 181 (4617) :1199-1200
[5]   Coumarin-based luminescent ligand that forms helicates with dicationic metal ions [J].
Bullock, Sam J. ;
Felton, Cara E. ;
Fennessy, Rebecca V. ;
Harding, Lindsay P. ;
Andrews, Michael ;
Pope, Simon J. A. ;
Rice, Craig R. ;
Riis-Johannessen, T. .
DALTON TRANSACTIONS, 2009, (47) :10570-10573
[6]  
Chandra Sangita, 2012, Asian Pacific Journal of Tropical Biomedicine, V2, pS178
[7]   Design of new cognition enhancers: From computer prediction to synthesis and biological evaluation [J].
Geronikaki, AA ;
Dearden, JC ;
Filimonov, D ;
Galaeva, I ;
Garibova, TL ;
Gloriozova, T ;
Krajneva, V ;
Lagunin, A ;
Macaev, FZ ;
Molodavkin, G ;
Poroikov, VV ;
Pogrebnoi, SI ;
Shepeli, F ;
Voronina, TA ;
Tsitlakidou, M ;
Vlad, L .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (11) :2870-2876
[8]  
Ghazaryan Artyom V., 2007, Cardiovascular & Hematological Disorders - Drug Targets, V7, P170, DOI 10.2174/187152907781745233
[9]   Substituted coumarins as potent 5-lipoxygenase inhibitors [J].
Grimm, EL ;
Brideau, C ;
Chauret, N ;
Chan, CC ;
Delorme, D ;
Ducharme, Y ;
Ethier, D ;
Falgueyret, JP ;
Friesen, RW ;
Guay, J ;
Hamel, P ;
Riendeau, D ;
Soucy-Breau, C ;
Tagari, P ;
Girard, Y .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (09) :2528-2531
[10]   Trimethylsilyl isothiocyanate (TMSNCS): an efficient reagent for the one-pot synthesis of mercapto-1,2,4-triazoles [J].
Guda, Dinneswara Reddy ;
Wang, Tengjiao ;
Cho, Hyeon Mo ;
Lee, Myong Euy .
TETRAHEDRON LETTERS, 2012, 53 (39) :5238-5242