Header menu link for other important links
X
Synthesis of Coumarins in Search of Better Nonpeptidic HIV Protease Inhibitors
A K MITRA, A DE, N KARCHAUDHURI, S K MISRA, A K MUKHOPADHYAY
Published in INDIAN CHEMICAL SOC
1998
Volume: 75
   
Issue: 43750
Pages: 666 - 671
Abstract
3-Substituted-4-hydroxycoumarins have been recently identified as active nonpeptidic HIV protease inhibitors. In order to get more potent inhibitors, synthesis of a number of 3-substituted-4-hydroxycoumarins have been designed. Nucleophilicity of C-3 in 4-hydroxycoumarin is exploited by reacting with an electrophile 3-carbethoxycoumarin to achieve a new C-3 substituted-4-hydroxycoumarin. But the product identified is a benzopyranodicoumarin (2), which is also obtained by the reaction of 4-hydroxycoumarin with salicylaldehyde. However, the reaction of 4-hydroxycoumarin with a number of 2-oxygenated aldehydes 4b-e affords dicoumarols (5a-d) only. On the contrary, with 2,4,5-trimethoxybenzaldehyde (4f), a benzopyranodicoumarin (6a) is formed. The reaction of 4-hydroxycoumarin with 6-bromo-3,4-methylenedioxybenzaldehyde (4g) and 6-bromo-3,4-dimethoxybenzaldehyde (4h), when treated separately, furnishes benzopyranodicoumarin (6b) and benzopyranocoumarin (7) respectively. In both the cases, unusual nucleophilic aromatic substitution of bromine occurs in electron-rich aromatic systems without any catalyst.
About the journal
JournalJournal of the Indian Chemical Society
PublisherINDIAN CHEMICAL SOC
ISSN0019-4522