A convenient synthesis of medicinally important coumarins and their substituted analogs

ORGN 525

Nawal K. Sharma, nks6@pitt.edu1, Pramod K. Sharma, pramod_sharma47@rediffmail.com2, Kausik Ghosh2, and Daya S. Seth2. (1) Department of Bioengineering, University of Pittsburgh, 721 Parran Hall, 130 DeSoto Street, Pittsburgh, PA 15213, (2) Department of Chemistry, St. John's College, Agra, Chemical Research Laboratories, Agra, India
Coumarins and their derivatives, both of natural and synthetic origin are well known for their broad spectrum of biological activities. Some of the coumarin analogues have been identified as active non-peptidic HIV protease inhibitors. The importance of coumarins in medcinal chemistry marked greatly for their uses as sedative, cytogenetic, anticoagulant, analgesic, anti-inflammatory agents in addition to the anti-microbial applications worldwide. The wide range of applications prompted us to synthesize analogues of these novel coumarins with varying and unique substitution patterns.

In our present study, we have synthesized set of these coumarins by the condensation of various azo salicylaldehydes with malonomic acids having varying substitution pattern in each case. The synthetic studies also resulted in the formation of corresponding Schiffs bases during coumarins synthesis as a minor product possibly by the hydrolysis of reactive methylene component to the free amine and followed by condensation with the aldehydes. The separation and purification of Schiff's base and coumarins were achieved based on the marked difference in their solubility in ethyl alcohol. The structures were confirmed by their H-NMR, IR and mass spectral data.

Details of experimental procedure, purification and spectroscopic characterization methods will be presented during the meeting.

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Sci-Mix

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006