Abstract
4-(Bromomethyl) coumarins 1 have been reacted with vanillins, 2 and 2A to obtain the corresponding ethers 3 and 5. Ethers 3 have been reacted with ethyl cyanoacetate to obtain the unsaturated esters 4. Ethers 5 have been converted to the corresponding 4-(2'-benzo[b] furanyl) coumarins 6 by an intramolecular aldol condensation. Eight compounds have been screened for their anti-inflammatory activity. Out of these the 5,6-benzo-4-2'-benzo[b]furanyl) coumarin (6c) and the aryloxymethyl coumarin (4) with p-formyl group were found to be most active.
MeSH terms
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Animals
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Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
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Anti-Inflammatory Agents, Non-Steroidal / toxicity
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Aspirin / pharmacology
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Benzaldehydes / chemistry*
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Carrageenan
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Coumarins / chemical synthesis*
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Coumarins / pharmacology*
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Edema / chemically induced
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Edema / prevention & control
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Ethers / chemical synthesis
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Ethers / pharmacology
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Female
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Granuloma / chemically induced
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Granuloma / prevention & control
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Indicators and Reagents
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Magnetic Resonance Spectroscopy
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Male
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Pain Measurement / drug effects
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Rats
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Rats, Wistar
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Reaction Time / drug effects
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Spectrophotometry, Infrared
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Stomach Ulcer / chemically induced
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Stomach Ulcer / pathology
Substances
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Anti-Inflammatory Agents, Non-Steroidal
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Benzaldehydes
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Coumarins
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Ethers
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Indicators and Reagents
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Carrageenan
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vanillin
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Aspirin