An efficient and eco-friendly synthesis and evaluation of antibactrial activity of pyrano[2,3-c]pyrazole derivatives

被引:39
作者
Mamaghani, Manouchehr [1 ]
Nia, Roghayeh Hossein [1 ]
Shirini, Farhad [1 ]
Tabatabaeian, Khalil [1 ]
Rassa, Mehdi [2 ]
机构
[1] Univ Guilan, Dept Chem, Fac Sci, Rasht, Iran
[2] Univ Guilan, Dept Biol, Fac Sci, Rasht, Iran
关键词
Hydrazine hydrate; Pyrano[2,3-c]pyrazole; Solvent-free; Ionic liquid; Antibacterial; Spiro; ONE-POT SYNTHESIS; REGIOSELECTIVE SYNTHESIS; IONIC LIQUID; CATALYST; IDENTIFICATION; MICROWAVE; FACILE; WATER;
D O I
10.1007/s00044-014-1271-y
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A rapid, straightforward, and highly efficient one-pot synthesis of pyrano[2,3-c]pyrazole derivatives and spiro-conjugated pyrano[2,3-c]pyrazole has been developed based on newly introduced and environmentally benign Bronsted-acidic ionic liquid catalyst [DMBSI]HSO4 via one-pot four-component reaction under solvent-free conditions. The synthesized compounds were screened for their antibacterial activities against both gram-negative (Pseudomonas aeruginosa and Escherichia coli) and gram-positive (Micrococcus luteus and Bacillus subtilis) bacteria.
引用
收藏
页码:1916 / 1926
页数:11
相关论文
共 40 条
[31]   Catalytic reactions in ionic liquids [J].
Sheldon, R .
CHEMICAL COMMUNICATIONS, 2001, (23) :2399-2407
[32]   An efficient and simple approach for the synthesis of pyranopyrazoles using imidazole (catalytic) in aqueous medium, and the vibrational spectroscopic studies on 6-amino-4-(4′-methoxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4-dihydropyrano[2,3-c]pyrazole using density functional theory [J].
Siddekha, Aisha ;
Nizam, Aatika ;
Pasha, M. A. .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2011, 81 (01) :431-440
[33]   Enantioselective chemo- and bio-catalysis in ionic liquids [J].
Song, CE .
CHEMICAL COMMUNICATIONS, 2004, (09) :1033-1043
[34]   Identification of isoflavone derivatives as effective anticryptosporidial agents in vitro and in vivo [J].
Stachulski, AV ;
Berry, NG ;
Low, ACL ;
Moores, SL ;
Row, E ;
Warhurst, DC ;
Adagu, LS ;
Rossignol, JF .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (04) :1450-1454
[35]   6H-benzo[c]chromen-6-one derivatives as selective ERβ agonists [J].
Sun, WY ;
Cama, LD ;
Birzin, ET ;
Warrier, S ;
Locco, L ;
Mosley, R ;
Hammond, ML ;
Rohrer, SP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (06) :1468-1472
[36]   Rapid four-component reactions in water: synthesis of pyranopyrazoles [J].
Vasuki, Gnanasambandam ;
Kumaravel, Kandhasamy .
TETRAHEDRON LETTERS, 2008, 49 (39) :5636-5638
[37]   Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells [J].
Wang, JL ;
Liu, DX ;
Zhang, ZJ ;
Shan, SM ;
Han, XB ;
Srinivasula, SM ;
Croce, CM ;
Alnemri, ES ;
Huang, ZW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2000, 97 (13) :7124-7129
[38]   Room-temperature ionic liquids. Solvents for synthesis and catalysis [J].
Welton, T .
CHEMICAL REVIEWS, 1999, 99 (08) :2071-2083
[39]  
Zaki MEA, 2006, Z NATURFORSCH C, V61, P1
[40]   A facile one pot synthesis of pyrano[2,3-c]pyrazole derivatives under microwave irradiation [J].
Zhou, JF ;
Tu, SJ ;
Zhu, HQ ;
Zhi, SJ .
SYNTHETIC COMMUNICATIONS, 2002, 32 (21) :3363-3366