Synthesis and antibacterial activity of ethyl 2-amino-6-methyl-5-oxo-4-aryl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate

被引：32
作者：
Asghari, Sakineh [1 ,2 ]
Ramezani, Samaneh [1 ]
Mohseni, Mojtaba [2 ,3 ]
机构：
[1] Univ Mazandaran, Dept Organ Chem, Fac Chem, Babol Sar 4741695447, Iran
[2] Univ Mazandaran, Nano & Biotechnol Res Grp, Babol Sar 4741695447, Iran
[3] Univ Mazandaran, Dept Microbiol, Fac Sci, Babol Sar 4741695447, Iran
来源：
CHINESE CHEMICAL LETTERS | 2014年 / 25卷 / 03期
关键词：
Three-component reaction; Pyranoquinoline; 4-Dimethyl aminopyridine (DMAP); Antibacterial activity; ONE-POT SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; 3-COMPONENT; DERIVATIVES; PYRANOQUINOLINE;
D O I：
10.1016/j.cclet.2013.12.010
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The three-component reaction of 4-hydroxy-1-methyl-2(1H)-quinolinone, aromatic aldehydes and ethyl cyanoacetate was carried out in the presence of a catalytic amount of 4-dimethyl aminopyridine (DMAP) in aqueous ethanol. The reactions result in the formation of pyranoquinoline derivatives in excellent yields. Antibacterial activity has been evaluated against Gram positive and Gram negative bacteria for some of the synthesized compounds. The results indicated that these compounds are moderately effective against bacterial growth and their effectiveness is highest against Pseudomonas aeruginosa. (C) 2013 Sakineh Asghari. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码：431 / 434
页数：4
相关论文
共 32 条
[1]  
Afonso A., 1993, US Patent, Patent No. [5179093A, 5179093]
[2]  
Afonso A., 1995, US Patent, Patent No. [5,382,572, 5382572]
[3]   Regio and diastereoselective synthesis of functionalized 2,3-dihydrofuro[3,2-c]coumarins via a one-pot three-component reaction [J].
Altieri, Elisa ;
Cordaro, Massimiliano ;
Grassi, Giovanni ;
Risitano, Francesco ;
Scala, Angela .
TETRAHEDRON, 2010, 66 (49) :9493-9496
[4]   A facile route to N-acetyl α,β-unsaturated γ-lactam derivatives using ethyl acetamidocyanoacetate and dialkyl acetylenedicarboxylate in the presence of triphenylphosphine [J].
Asghari, Sakineh ;
Taibakhsh, Mahmood ;
Taghipour, Vali .
TETRAHEDRON LETTERS, 2008, 49 (11) :1824-1827
[5]   One pot three-component regioselective and diastereoselective synthesis of halogenated pyrido[2,1-b][1,3]oxazines [J].
Asghari, Sakineh ;
Habibi, Ahmad Khabbazi .
TETRAHEDRON, 2012, 68 (43) :8890-8898
[6]   Synthesis of Halogenated α,β-Unsaturated γ-Butyrolactone Derivatives by Triphenylphosphine-Catalyzed Cyclization of α-Halogeno Ketones with Dialkyl Acetylenedicarboxylates (=Dialkyl But-2-ynedioates) [J].
Asghari, Sakineh ;
Habibi, Ahmad Khabbazi .
HELVETICA CHIMICA ACTA, 2012, 95 (05) :810-817
[7]   One-pot synthesis of 4-arylquinolines from aromatic aminoketones and vinylphosphonium salts [J].
Asghari, Sakineh ;
Qandalee, Mohammad ;
Naderi, Zahra ;
Sobhaninia, Zahra .
MOLECULAR DIVERSITY, 2010, 14 (03) :569-574
[8]   Three-Component, One-Pot Synthesis of New Functionalized Pyrrolines [J].
Asghari, Sakineh ;
Qandalee, Mohammad .
SYNTHETIC COMMUNICATIONS, 2010, 40 (14) :2172-2177
[9]   A green one-pot multicomponent synthesis of 4H-pyrans and polysubstituted aniline derivatives of biological, pharmacological, and optical applications using silica nanoparticles as reusable catalyst [J].
Banerjee, Subhash ;
Horn, Alissa ;
Khatri, Hari ;
Sereda, Grigoriy .
TETRAHEDRON LETTERS, 2011, 52 (16) :1878-1881
[10]   CHEMICAL AND BIOACTIVE CONSTITUENTS FROM ZANTHOXYLUM SIMULANS [J].
CHEN, IS ;
WU, SJ ;
TSAI, IL ;
WU, TS ;
PEZZUTO, JM ;
LU, MC ;
CHAI, H ;
SUH, N ;
TENG, CM .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (09) :1206-1211
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