Abstract
A new, convenient and high yield route to luzindole, the most commonly used melatonin receptor antagonist, is described. The new method involves the Sonogashira coupling reaction between 2-iodoaniline and 3-phenyl-1-propyne followed by cyclisation of the adduct formed, C-3 indole nitroolefination with 1-(dimethylamino)-2-nitroethylene/TFA, reduction to the respective tryptamine and finally acetylation.
Keywords: Luzindole, melatonin receptor antagonist, ortho-alkynylanilines, nitroolefination, 2-benzyltryptamides
Letters in Organic Chemistry
Title: Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis
Volume: 5 Issue: 6
Author(s): Andrew Tsotinis and Pandelis A. Afroudakis
Affiliation:
Keywords: Luzindole, melatonin receptor antagonist, ortho-alkynylanilines, nitroolefination, 2-benzyltryptamides
Abstract: A new, convenient and high yield route to luzindole, the most commonly used melatonin receptor antagonist, is described. The new method involves the Sonogashira coupling reaction between 2-iodoaniline and 3-phenyl-1-propyne followed by cyclisation of the adduct formed, C-3 indole nitroolefination with 1-(dimethylamino)-2-nitroethylene/TFA, reduction to the respective tryptamine and finally acetylation.
Export Options
About this article
Cite this article as:
Tsotinis Andrew and Afroudakis A. Pandelis, Melatonin Receptor Antagonist Luzindole: A Facile New Synthesis, Letters in Organic Chemistry 2008; 5 (6) . https://dx.doi.org/10.2174/157017808785740561
DOI https://dx.doi.org/10.2174/157017808785740561 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
- Author Guidelines
- 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
-
Does Mechanism of Drug Action Matter to Inform Rational Polytherapy in Epilepsy?
CNS & Neurological Disorders - Drug Targets Stress in Gastrointestinal Tract and Stable Gastric Pentadecapeptide BPC 157. Finally, do we have a Solution?
Current Pharmaceutical Design Pharmacological and Non-pharmacological Therapies of Cognitive Impairment in Multiple Sclerosis
Current Neuropharmacology The Use of SIFT-MS to Investigate Headspace Aldehydes as Markers of Lipid Peroxidation
Current Analytical Chemistry Voice Markers of Lexical Access in Mild Cognitive Impairment and Alzheimer's Disease
Current Alzheimer Research Insight into Pain Modulation: Nociceptors Sensitization and Therapeutic Targets
Current Drug Targets P2X7 Receptor-Associated Programmed Cell Death in the Pathophysiology of Hemorrhagic Stroke
Current Neuropharmacology Inflammation in Neurodegenerative Disorders: Friend or Foe?
Current Aging Science Purine Molecules as Hypnogenic Factors Role of Adenosine, ATP, and Caffeine
Central Nervous System Agents in Medicinal Chemistry Dopamine Administration in Very Low Birth Weight Preterm Infants:Emerging Issues on Endocrine Effects
Current Pediatric Reviews Clinical Pharmacology of Serotonin Receptor Type 3 (5-HT3) Antagonists
Current Medicinal Chemistry - Central Nervous System Agents A Disposable, Highly Sensitive Biosensing System: Determination of Haptoglobin as a Significant Acute Phase Biomarker
Current Analytical Chemistry Unsuspected Intrinsic Property of Melanin to Dissociate Water Can Be Used for the Treatment of CNS Diseases
CNS & Neurological Disorders - Drug Targets Role of FAS in HIV Infection
Current HIV Research Mitochondrial Dysfunction and Lipid Homeostasis
Current Drug Metabolism Pharmacological Treatment of Attention Deficit Hyperactivity Disorder (ADHD): A Systematic Review of Recent Data
Current Psychopharmacology Translating Cancer Biomarker Discoveries to Clinical Tests: What should be Considered?
Recent Patents on Biomarkers Metal and Inflammatory Targets for Alzheimers Disease
Current Drug Targets TRP Channels as Novel Targets for Endogenous Ligands: Focus on Endocannabinoids and Nociceptive Signalling
Current Neuropharmacology Recent Progress in the Development of Adenosine Receptor Ligands as Antiinflammatory Drugs
Current Topics in Medicinal Chemistry