Abstract
Grignard reactions with the Weinreb amide (N-methoxy-N-methylamide) of indole-3-acetic acid provide a facile access to indol- 3-yl ketones, which are potential agonists of the human aryl hydrocarbon receptor ("dioxin receptor"). Addition of one equivalent of the MgBr2•THF complex avoids discolorations and oxidative side reactions, for which the 3-indolyl system is notorious. The product ketones carry aliphatic, olefinic, as well as (hetero)aromatic residues. The reaction conditions were thoroughly optimized, and full sets of analytical data including example crystal structures are presented.
Keywords: (3-indolyl)methyl ketones, indole-3-acetic acid, Weinreb amides, Grignard reaction, human arylhydrocarbon receptor.
Current Organic Synthesis
Title:Synthesis of 2-(Indol-3-yl)-ethanone-based Arylhydrocarbon Receptor Agonist Candidates via Weinreb Amides of Indole-3-acetic Acid.
Volume: 10 Issue: 5
Author(s): Martina Opietnik, Alois Jungbauer, Kurt Mereiter and Thomas Rosenau
Affiliation:
Keywords: (3-indolyl)methyl ketones, indole-3-acetic acid, Weinreb amides, Grignard reaction, human arylhydrocarbon receptor.
Abstract: Grignard reactions with the Weinreb amide (N-methoxy-N-methylamide) of indole-3-acetic acid provide a facile access to indol- 3-yl ketones, which are potential agonists of the human aryl hydrocarbon receptor ("dioxin receptor"). Addition of one equivalent of the MgBr2•THF complex avoids discolorations and oxidative side reactions, for which the 3-indolyl system is notorious. The product ketones carry aliphatic, olefinic, as well as (hetero)aromatic residues. The reaction conditions were thoroughly optimized, and full sets of analytical data including example crystal structures are presented.
Export Options
About this article
Cite this article as:
Opietnik Martina, Jungbauer Alois, Mereiter Kurt and Rosenau Thomas, Synthesis of 2-(Indol-3-yl)-ethanone-based Arylhydrocarbon Receptor Agonist Candidates via Weinreb Amides of Indole-3-acetic Acid., Current Organic Synthesis 2013; 10 (5) . https://dx.doi.org/10.2174/1570179411310050012
DOI https://dx.doi.org/10.2174/1570179411310050012 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |

- 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
Related Articles
-
Physiological Functions of Presenilins; Beyond γ-Secretase
Current Pharmaceutical Biotechnology Therapy Against Ischemic Injury
Current Pharmaceutical Design Application of Mesenchymal Stem Cells in Melanoma: A Potential Therapeutic Strategy for Delivery of Targeted Agents
Current Medicinal Chemistry Cardioprotective Effects of the Polyphenol Hydroxytyrosol from Olive Oil
Current Drug Targets Plasmid-Mediated Muscle-Targeted Gene Therapy for Circulating Therapeutic Protein Replacement: A Tale of the Tortoise and the Hare?
Current Gene Therapy Wnt Signaling in Renal Cancer
Current Drug Targets Enrichment of Up-regulated and Down-regulated Gene Clusters Using Gene Ontology, miRNAs and lncRNAs in Colorectal Cancer
Combinatorial Chemistry & High Throughput Screening Sp/KLF Family and Tumor Angiogenesis in Pancreatic Cancer
Current Pharmaceutical Design Lung Cancer Surgery in Patients with Chronic Obstructive Pulmonary Disease (COPD): Surgical Selection Challenges and Clinical Outcomes
Current Respiratory Medicine Reviews Regulation of Hepatic Transporters by Xenobiotic Receptors
Current Drug Metabolism Omacetaxine as an Anticancer Therapeutic: What is Old is New Again
Current Pharmaceutical Design Targeting Invasion Induction as a Therapeutic Strategy for the Treatment of Cancer
Current Cancer Drug Targets Stability Studies on Piroxicam Encapsulated Niosomes
Current Drug Delivery Hypothetical Link Between Infertility and Genetically Modified Food
Recent Patents on Food, Nutrition & Agriculture Transductional Targeting of Adenoviral Cancer Gene Therapy
Current Gene Therapy Brain Targeting of siRNA via Intranasal Pathway
Current Pharmaceutical Design Biodegradable Polymeric Nanoparticles as the Delivery Carrier for Drug
Current Drug Delivery Editorial [Hot Topic: Drug Delivery Strategies in Targeting Cancer:Current Concepts and Future Developments (Guest Editor: Jose L. Arias)]
Current Drug Targets Application of Plasmonic Gold Nanoparticle for Drug Delivery System
Current Drug Targets Brain Tumor-Related Epilepsy
Current Neuropharmacology