Abstract
A variety of natural and unnatural molecules containing a 5-hydroxyindole moiety have displayed strong pharmacological activities. In this context the Nenitzescu reaction has proven to be extremely useful for the preparation of 5- hydroxyindoles directly from simple and accessible materials like 1,4-benzoquinone and enamines. This review will summarize recent applications for the synthesis of complex 5-hydroxyindole derivatives such as pyrimido[4,5-b]indol-4- amines, 5H-benzo[b]carbazoles, 5-hydroxynaltrindolomorphinans, and 3-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)- 1H-indol-5-yloxy]propylphosphonic acid (LY311727) which possess important biological activities. The Mechanism of the Nenitzescu reaction is discussed and as is recent utilization of solid phase chemistry to the Nenitzescu reaction.
Current Organic Chemistry
Title: Synthetic Applications of the Nenitzescu Reaction to Biologically Active 5-Hydroxyindoles
Volume: 12 Issue: 9
Author(s): Shivaputra A. Patil, Renukadevi Patil and Duane D. Miller
Affiliation:
Abstract: A variety of natural and unnatural molecules containing a 5-hydroxyindole moiety have displayed strong pharmacological activities. In this context the Nenitzescu reaction has proven to be extremely useful for the preparation of 5- hydroxyindoles directly from simple and accessible materials like 1,4-benzoquinone and enamines. This review will summarize recent applications for the synthesis of complex 5-hydroxyindole derivatives such as pyrimido[4,5-b]indol-4- amines, 5H-benzo[b]carbazoles, 5-hydroxynaltrindolomorphinans, and 3-[3-(amidomethyl)-2-ethyl-1-(phenylmethyl)- 1H-indol-5-yloxy]propylphosphonic acid (LY311727) which possess important biological activities. The Mechanism of the Nenitzescu reaction is discussed and as is recent utilization of solid phase chemistry to the Nenitzescu reaction.
Export Options
About this article
Cite this article as:
Patil A. Shivaputra, Patil Renukadevi and Miller D. Duane, Synthetic Applications of the Nenitzescu Reaction to Biologically Active 5-Hydroxyindoles, Current Organic Chemistry 2008; 12 (9) . https://dx.doi.org/10.2174/138527208784567223
DOI https://dx.doi.org/10.2174/138527208784567223 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- 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
- Announcements
Related Articles
-
Mesenchymal Stem Cells as Mediators of Neural Differentiation
Current Stem Cell Research & Therapy Targeting Kynurenine 3-Monooxygenase (KMO): Implications for Therapy in Huntingtons Disease
CNS & Neurological Disorders - Drug Targets Nutraceuticals against Neurodegeneration: A Mechanistic Insight
Current Neuropharmacology Foreword
Recent Patents on CNS Drug Discovery (Discontinued) The Role of Iron Toxicity in Oxidative Stress-induced Cellular Degeneration in Down Syndrome: Protective Effects of Phenolic Antioxidants
Current Nutrition & Food Science Recent Patents on Proteases and Kinases as Anti-Infective Agents: A Review
Recent Patents on Anti-Infective Drug Discovery PET Studies of Brain Monoamine Transporters
Current Pharmaceutical Design Renin-Angiotensin-Aldosterone System: A Current Drug Target for the Management of Neuropathic Pain
Current Drug Targets Editorial :
Recent Patents on CNS Drug Discovery (Discontinued) Monoamine Oxidase Inhibitors as Neuroprotective Agents in Age-Dependent Neurodegenerative Disorders
Current Pharmaceutical Design Liver Growth Factor as a Tissue Regenerating Factor in Neurodegenerative Diseases
Recent Patents on CNS Drug Discovery (Discontinued) RNA Interference (RNAi) Patents and Human Health Related Applications of RNAi
Recent Patents on DNA & Gene Sequences Nanotechnology and Antioxidant Therapy: An Emerging Approach for Neurodegenerative Diseases
Current Medicinal Chemistry Evaluation of Current Pharmacological Treatment Options in the Management of Rett Syndrome: From the Present to Future Therapeutic Alternatives.
Current Clinical Pharmacology Editorial [ Therapeutics for Protein Misfolding Diseases Executive Editor: Claudio Soto ]
Current Pharmaceutical Design Is Amyloid Binding Alcohol Dehydrogenase a Drug Target for Treating Alzheimer’s Disease?
Current Alzheimer Research Cannabinoid Receptor Type 2 Activation Yields Delayed Tolerance to Focal Cerebral Ischemia
Current Neurovascular Research Calpain and Its Involvement in the Pathophysiology of CNS Injuries and Diseases: Therapeutic Potential of Calpain Inhibitors for Prevention of Neurodegeneration
Current Drug Targets - CNS & Neurological Disorders Tet-On Systems For Doxycycline-inducible Gene Expression
Current Gene Therapy Efficacy of HGF Gene Transfer for Various Nervous Injuries and Disorders
Central Nervous System Agents in Medicinal Chemistry