Article

Natural and synthetic 2,2-dimethylpyranocoumarins with antibacterial activity.

Division of Pharmacognosy and Natural Products Chemistry, Department of Pharmacy, University of Athens, Panepistimiopolis, Zografou, GR-15771 Athens, Greece.
Journal of Natural Products (impact factor: 3.13). 02/2005; 68(1):78-82. DOI:10.1021/np0497447 pp.78-82
Source: PubMed

ABSTRACT A new efficient synthetic approach to the natural coumarins 5-hydroxyseselin (5), 5-methoxyseselin (3), and (+/-) cis-grandmarin (9) is described as well as the synthesis of some new derivatives in the 5-methoxyseselin series (10-15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products. The type of fusion of the pyrano ring in all cases has been established by 2D NMR spectroscopy. The compounds have been studied for their in vitro antibacterial activity, which has been compared with that of some previously synthesized seselin derivatives. The most active compounds were 3, 7, 8, 11, and 14. Some structure-activity relationships are discussed.

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Keywords

2D NMR spectroscopy
 
5-methoxyseselin
 
5-methoxyseselin series
 
active compounds
 
cases
 
compounds
 
natural coumarins 5-hydroxyseselin
 
natural coumarins 7-hydroxyalloxanthyletin
 
new derivatives
 
new efficient synthetic approach
 
pyrano ring
 
secondary products
 
structure-activity relationships
 
synthesized seselin derivatives
 
vitro antibacterial activity