Triphenyl Phosphite-mediated “Green” Synthesis of Novel Carboxycoumarin Amides

Author(s): Pramod K. Sharma, Divya Mathur, Shashwat Malhotra, Neha Rana, Brajendra K. Singh, Ashok K. Prasad, Anjani J. Varma, Najam A. Shakil, Balaram Ghosh, Christophe Len, Ramesh C. Kuhad, Francois Jerome, Virinder S. Parmar*

Journal Name: Current Green Chemistry

Volume 3 , Issue 4 , 2016

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Graphical Abstract:


Background: A library of eleven novel coumarin carboxamides were efficiently synthesized in high yields, by triphenyl phosphite-activated direct condensation of coumarin carboxylic acids and various alkyl amines.

Methods: The procedure has several advantages and addresses key “Green” chemistry issues, such as one step condensation, no prior activation of coumarin carboxylic acids by toxic chlorinating agents, no toxic by-products are produced and does not involve troublesome/hazardous disposal of the catalyst. The synthesized coumarin carboxamides were examined for their antiinflammatory activity by measuring the effect on tumour necrosis factor-α (TNF-α) induced expression of intercellular adhesion moledule-1 (ICAM-1).

Conclusion: The structure-activity relationship (SAR) studies revealed that N-dodecyl-7- hydroxy-4-methyl-2-oxo-2H-chromene-8-carboxamide (23) exhibited the maximum inhibition (90%) of ICAM-1 expression at an IC50 value of 43 μM.

Keywords: Triphenyl phosphite, coumarin carboxamides, green synthesis, TNF-α, ICAM-1, anti-inflammatory.

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Article Details

Year: 2016
Page: [366 - 373]
Pages: 8
DOI: 10.2174/2213346104666170306100140

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