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
About this article
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 |

- Author Guidelines
- Bentham Author Support Services (BASS)
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Template Dependent Human DNA Polymerases
Current Topics in Medicinal Chemistry Static Cerebral Blood Flow Autoregulation in Humans
Current Hypertension Reviews HLA-G Expression in Cancers: Potential Role in Diagnosis, Prognosis and Therapy
Endocrine, Metabolic & Immune Disorders - Drug Targets Proresolution Mediators and Receptors: Novel Drug Targets for Enhancing Pharmacological Armamentarium against Periodontal Inflammation
Infectious Disorders - Drug Targets An Intricate Mechanism of Action of Avonex in Relapsing Remitting Multiple Sclerosis Patients: Variation of Serum Titre of Interleukin-17A, Interleukin-10 and Transforming Growth Factor-β
CNS & Neurological Disorders - Drug Targets Apoptosis and Autoimmune Disease
Current Medicinal Chemistry - Anti-Inflammatory & Anti-Allergy Agents Biomarkers in Atrial Fibrillation and Heart Failure
Current Medicinal Chemistry PLK1 Inhibition: Prospective Role for the Treatment of Pediatric Tumors
Current Drug Targets Structural and Functional Properties of Human Multidrug Resistance Protein 1 (MRP1/ABCC1)
Current Medicinal Chemistry Patent Annotations
Recent Patents on Inflammation & Allergy Drug Discovery A Critical Evaluation of Adenosine A2A Receptors as Potentially “Druggable” Targets in Huntingtons Disease
Current Pharmaceutical Design S-Nitrosothiols as Nitric Oxide-Donors: Chemistry, Biology and Possible Future Therapeutic Applications
Current Medicinal Chemistry Inflammatory Markers in SIRS, Sepsis and Septic Shock
Current Medicinal Chemistry Repositioning of DHFR Inhibitors
Current Topics in Medicinal Chemistry Crystallization and Preliminary X-Ray Crystallographic Studies on SICLP, a Novel Human Glyco_18 Domain – Containing Protein
Protein & Peptide Letters Chemopreventive Effects of Conjugated Linolenic Acids (CLN) Occurring in Plant Seed Oils
Current Nutrition & Food Science The Role of Platelet/Lymphocyte Serotonin Transporter in Depression and Beyond
Current Drug Targets Selective Activation of Intracellular Signalling Pathways in Dendritic Cells for Cancer Immunotherapy
Anti-Cancer Agents in Medicinal Chemistry The Role of Chemokines and their Receptors in Tumor Progression and Invasion: Potential New Targets of Biological Therapy
Current Cancer Therapy Reviews Chemokines and Chemokine Receptors as Targets in the Therapy of Psoriasis
Current Drug Targets - Inflammation & Allergy