Abstract
Highly functionalized regio- and stereoisomers of 1,2,3-triazole-substituted cyclopentanes were prepared in six steps from either bicyclic β-lactam 7 or γ-lactam 23 by 1,3-dipolar cycloaddition of the azido cyclopentanol intermediates with acetylenes. The reactions of azido aminocyclopentanols with non-symmetric acetylenes resulted regioselectively in the corresponding 1,4-disubstitued triazole derivatives under both thermal and Cu(I)-catalysed conditions. These compounds can be regarded as highly functionalized 1,2,3-triazole-modified carbocyclic nucleoside analogues.
Keywords: Amino alcohols, azides, carbocyclic nucleosides, click chemistry, 1,3-dipolar cycloaddition, enzymes, 1,2,3- triazoles, antiviral activity, Triazole-modified, multifunctionalized cyclopentanes
Letters in Organic Chemistry
Title: Synthesis of Regio- and Stereoisomers of Highly Functionalized 1,2,3- Triazole-substituted Cyclopentanes
Volume: 8 Issue: 3
Author(s): Lorand Kiss, Eniko Forro and Ferenc Fulop
Affiliation:
Keywords: Amino alcohols, azides, carbocyclic nucleosides, click chemistry, 1,3-dipolar cycloaddition, enzymes, 1,2,3- triazoles, antiviral activity, Triazole-modified, multifunctionalized cyclopentanes
Abstract: Highly functionalized regio- and stereoisomers of 1,2,3-triazole-substituted cyclopentanes were prepared in six steps from either bicyclic β-lactam 7 or γ-lactam 23 by 1,3-dipolar cycloaddition of the azido cyclopentanol intermediates with acetylenes. The reactions of azido aminocyclopentanols with non-symmetric acetylenes resulted regioselectively in the corresponding 1,4-disubstitued triazole derivatives under both thermal and Cu(I)-catalysed conditions. These compounds can be regarded as highly functionalized 1,2,3-triazole-modified carbocyclic nucleoside analogues.
Export Options
About this article
Cite this article as:
Kiss Lorand, Forro Eniko and Fulop Ferenc, Synthesis of Regio- and Stereoisomers of Highly Functionalized 1,2,3- Triazole-substituted Cyclopentanes, Letters in Organic Chemistry 2011; 8 (3) . https://dx.doi.org/10.2174/157017811795038359
DOI https://dx.doi.org/10.2174/157017811795038359 |
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
-
Identification of 1-Aryl-1H-1,2,3-triazoles as Potential New Antiretroviral Agents
Medicinal Chemistry Analysis of Biological Macromolecular Assemblies Using Static Light Scattering Methods
Current Organic Chemistry Artificial Carriers: A Strategy for Constructing Antigenic/Immunogenic Conjugates
Current Topics in Medicinal Chemistry Protective Effects of Low Dose Vorinostat on Cisplatin-Induced Nephrotoxicity in Rats
Current Molecular Pharmacology Synthesis and Cellular Pharmacology Studies of a Series of 2-amino-3-aroyl-4-substituted Thiophene Derivatives
Medicinal Chemistry Recent Advances on the Development of Pharmacotherapeutic Agents on the Basis of Human Serum Albumin
Current Pharmaceutical Design BSA Au Clusters as a Probe for Enhanced Fluorescence Detection Using Multipulse Excitation Scheme
Current Pharmaceutical Biotechnology Pathogenesis of and Therapeutic Strategies to Ameliorate the Transthyretin Amyloidoses
Current Pharmaceutical Design Overexpression, Purification and Characterization of Recombinant Salmon Calcitonin, A Therapeutic Protein, in Streptomyces Avermitilis
Protein & Peptide Letters Functional Calixarenes for Material and Life Science
Current Organic Chemistry Design and In vitro Validation of Multivalent Dendrimer Methotrexates as a Folate-targeting Anticancer Therapeutic
Current Pharmaceutical Design Thermal Stability and Phase Transitions in WO<sub>3</sub>-ZrO<sub>2</sub> and WO<sub>3</sub>-TiO<sub>2</sub> Composites
Innovations in Corrosion and Materials Science (Discontinued) The Development of Protein Chips for High Throughput Screening (HTS) of Chemically Labeling Small Molecular Drugs
Mini-Reviews in Medicinal Chemistry A Novel Gene Selection Method Based on Sparse Representation and Max-Relevance and Min-Redundancy
Combinatorial Chemistry & High Throughput Screening FLIM-FRET for Cancer Applications
Current Molecular Imaging (Discontinued) Synthesis of Some Benzothiazole Based Piperazine-Dithiocarbamate Derivatives and Evaluation of Their Anticancer Activities
Letters in Drug Design & Discovery Involvement of Cytoskeleton in AhR-Dependent CYP1A1 Expression
Current Drug Metabolism Simple C-2-Substituted Quinolines and their Anticancer Activity
Letters in Drug Design & Discovery Chemical Constituents and Biological Activity of Chinese Medicinal Herb ‘Xihuangcao’
Combinatorial Chemistry & High Throughput Screening Trizbenzim, Cu-Trizbenzim and Zn-Trizbenzim as G-Quadruplex Inducing and Stabilizing Compounds on Human Telomeric Sequence and their Anticancer Properties
Anti-Cancer Agents in Medicinal Chemistry