Synthesis, characterization, and antimicrobial activity of some new coumarin derivatives

被引:23
作者
Al-Rifai, Asma'a A. [3 ]
Ayoub, Mikdad T. [3 ]
Shakya, Ashok K. [2 ]
Abu Safieh, Kayed A. [3 ]
Mubarak, Mohammad S. [1 ]
机构
[1] Univ Jordan, Dept Chem, Amman 11942, Jordan
[2] Al Ahliyya Amman Univ, Fac Pharm & Med Sci, Amman, Jordan
[3] Hashemite Univ, Dept Chem, Fac Sci, Zarqa 13115, Jordan
关键词
7-Amino-4-methylcoumarin; Acetohydrazide; Spectral analysis; Antimicrobial activity; STATE PROTON-TRANSFER; BIOLOGICAL-ACTIVITY; SOLVENT-FREE; AGENTS; QUINOLONES; CHEMISTRY;
D O I
10.1007/s00044-011-9553-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A number of new [(4-methyl-2-oxo-2H-chromen-7-yl)amino]methylcoumarins (5a-c), benzofuran (6), and benzoxazol (7) were synthesized through the reaction of 7-amino-4-methylcoumarin (1) with a number of organic halides. In addition, series of N-substituted 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetohydrazide (11a-h) and (12a-d) were prepared from the reaction of 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetohydrazide (8) with corresponding heteroaryl/alkyl halides (2-4, 9, and 10). The synthesized compounds were characterized by elemental analysis and by spectroscopic techniques such as H-1-NMR, C-13-NMR, and mass spectrometry and were tested for their in vitro antimicrobial activity. The newly synthesized compounds exerted significant inhibitory activity against the growth of tested bacterial strains and a few of them are found to be potent antimicrobial agents.
引用
收藏
页码:468 / 476
页数:9
相关论文
共 29 条
[1]  
Abu-Shaireh EAM, 2009, European Patent, Patent No. [09250251.7-2117, 0925025172117]
[2]  
Abu-Shaireh EAM, 2009, Eur Pat Appl EP, Patent No. [2985394 A2, 2985394]
[3]   Synthesis, characterization and anti-HIV and antitumor activities of new coumarin derivatives [J].
Al-Soud, Yaseen A. ;
Al-Sa'doni, Haitham H. ;
Amajaour, Houssain A. S. ;
Salih, Kifah S. M. ;
Mubarak, Mohammad S. ;
Al-Masoudi, Najim A. ;
Jaber, Ihsan H. .
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2008, 63 (01) :83-89
[4]  
Al-Zghoul KH, 2005, HETEROCYCLES, V65, P2937
[5]  
[Anonymous], 1993, M7A3 NCCLS
[6]   KAl(SO4)2•12H2O (alum) a reusable catalyst for the synthesis of some 4-substituted coumarins via Pechmann reaction under solvent-free conditions [J].
Azizian, Javad ;
Mohammadi, Ali A. ;
Bidar, Ilyar ;
Mirzaei, Peiman .
MONATSHEFTE FUR CHEMIE, 2008, 139 (07) :805-808
[7]   Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity [J].
Borges, F ;
Roleira, F ;
Milhazes, N ;
Santana, L ;
Uriarte, E .
CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) :887-916
[8]   Synthesis, structural characterization, and in vitro antitumor activity of novel N-(6-chloro-1,1-dioxo-1,4,2-benzodithiazin-3-yl)arylsulfonamides [J].
Brzozowski, Zdzislaw ;
Saczewski, Franciszek ;
Slawinski, Jaroslaw ;
Bednarski, Patrick J. ;
Gruenert, Renate ;
Gdaniec, Maria .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (07) :2560-2572
[9]  
Burbuliene M. M., 2005, CHEMIJA, V16, P39
[10]   Chemistry and biological activity of natural and synthetic prenyloxycoumarins [J].
Curini, M ;
Cravotto, G ;
Epifano, F ;
Giannone, G .
CURRENT MEDICINAL CHEMISTRY, 2006, 13 (02) :199-222