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

[ Vol. 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   Pages 366 - 373 ( 8 )

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.

Affiliation:

Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, Molecular Immunology and Immunogenetics Laboratory, CSIR-Institute of Genomics and Integrative Biology, Mall Road, Delhi 110 007, Sorbonne Universites, Universite de Technologie de Compiegne, EA4297 Transformations Chimiques de la Matière Renouvelable, F-60203 Compiegne Cedex, School of Chemical Sciences, Central University of Haryana, Mahendragarh, Haryana 123 029, University of Poitiers, Ecole Nationale Superieure d`Ingenieurs de Poitiers, Institut de Chimie des Milieux et Materiaux de Poitiers, 1 rue Marcel Dore, 86073 Poitiers cedex 9, Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007

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