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.
Graphical Abstract
Current Green Chemistry
Title:Triphenyl Phosphite-mediated “Green” Synthesis of Novel Carboxycoumarin Amides
Volume: 3 Issue: 4
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 and Virinder S. Parmar*
Affiliation:
- Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007,India
Keywords: Triphenyl phosphite, coumarin carboxamides, green synthesis, TNF-α, ICAM-1, anti-inflammatory.
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.Export Options
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Cite this article as:
Sharma K. Pramod, Mathur Divya, Malhotra Shashwat, Rana Neha, Singh K. Brajendra, Prasad K. Ashok, Varma J. Anjani, Shakil A. Najam, Ghosh Balaram, Len Christophe , Kuhad C. Ramesh, Jerome Francois and Parmar S. Virinder*, Triphenyl Phosphite-mediated “Green” Synthesis of Novel Carboxycoumarin Amides, Current Green Chemistry 2016; 3 (4) . https://dx.doi.org/10.2174/2213346104666170306100140
DOI https://dx.doi.org/10.2174/2213346104666170306100140 |
Print ISSN 2213-3461 |
Publisher Name Bentham Science Publisher |
Online ISSN 2213-347X |
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