Abstract
Acyclic nucleoside analogues bearing phosphonomethoxy residues in the side chain (ANP) attract much attention due to a very beneficial combination of biological properties. Intensive work of organic chemists during the last two decades resulted in a large panel of new compounds that were evaluated as potential antiviral drugs. Herein, we present an overview of major chemical structures within the group of acyclic nucleoside analogues containing phosphonomethoxy side fragments and describe main aspects of their synthesis and antiviral potential. We also describe progress in "prodrug" approaches applied to this chemical group to improve pharmacokinetic profiles of the potential candidates. Chemical modifications in the molecule of parental ANP aimed at blocking of phosphonate charges resulted in a set of promising derivatives, two of which have been recently approved for treatment of hepatits B (Hepsera®) and HIV (Viread®). The preparation, antiviral properties and some aspects of metabolic transformations and pharmacokinetics of ANP prodrugs are discussed.
Keywords: Acyclic nucleoside analogues, phosphonomethoxy groups, prodrugs, antiviral properties
Current Medicinal Chemistry
Title: The Synthesis and Antiviral Properties of Acyclic Nucleoside Analogues with a Phosphonomethoxy Fragment in the Side Chain
Volume: 13 Issue: 24
Keywords: Acyclic nucleoside analogues, phosphonomethoxy groups, prodrugs, antiviral properties
Abstract: Acyclic nucleoside analogues bearing phosphonomethoxy residues in the side chain (ANP) attract much attention due to a very beneficial combination of biological properties. Intensive work of organic chemists during the last two decades resulted in a large panel of new compounds that were evaluated as potential antiviral drugs. Herein, we present an overview of major chemical structures within the group of acyclic nucleoside analogues containing phosphonomethoxy side fragments and describe main aspects of their synthesis and antiviral potential. We also describe progress in "prodrug" approaches applied to this chemical group to improve pharmacokinetic profiles of the potential candidates. Chemical modifications in the molecule of parental ANP aimed at blocking of phosphonate charges resulted in a set of promising derivatives, two of which have been recently approved for treatment of hepatits B (Hepsera®) and HIV (Viread®). The preparation, antiviral properties and some aspects of metabolic transformations and pharmacokinetics of ANP prodrugs are discussed.
Export Options
About this article
Cite this article as:
The Synthesis and Antiviral Properties of Acyclic Nucleoside Analogues with a Phosphonomethoxy Fragment in the Side Chain, Current Medicinal Chemistry 2006; 13 (24) . https://dx.doi.org/10.2174/092986706778521896
DOI https://dx.doi.org/10.2174/092986706778521896 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |
Call for Papers in Thematic Issues
Advances in Medicinal Chemistry: From Cancer to Chronic Diseases.
The broad spectrum of the issue will provide a comprehensive overview of emerging trends, novel therapeutic interventions, and translational insights that impact modern medicine. The primary focus will be diseases of global concern, including cancer, chronic pain, metabolic disorders, and autoimmune conditions, providing a broad overview of the advancements in ...read more
Approaches to the treatment of chronic inflammation
Chronic inflammation is a hallmark of numerous diseases, significantly impacting global health. Although chronic inflammation is a hot topic, not much has been written about approaches to its treatment. This thematic issue aims to showcase the latest advancements in chronic inflammation treatment and foster discussion on future directions in this ...read more
Cellular and Molecular Mechanisms of Non-Infectious Inflammatory Diseases: Focus on Clinical Implications
The Special Issue covers the results of the studies on cellular and molecular mechanisms of non-infectious inflammatory diseases, in particular, autoimmune rheumatic diseases, atherosclerotic cardiovascular disease and other age-related disorders such as type II diabetes, cancer, neurodegenerative disorders, etc. Review and research articles as well as methodology papers that summarize ...read more
Chalcogen-modified nucleic acid analogues
Chalcogen-modified nucleosides, nucleotides and oligonucleotides have been of great interest to scientific research for many years. The replacement of oxygen in the nucleobase, sugar or phosphate backbone by chalcogen atoms (sulfur, selenium, tellurium) gives these biomolecules unique properties resulting from their altered physical and chemical properties. The continuing interest in ...read more
- 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
-
Cyclin-Dependent Kinase-2 as a Target for Cancer Therapy: Progress in the Development of CDK2 Inhibitors as Anti-Cancer Agents
Current Medicinal Chemistry Targeting the AKT Pathway in Glioblastoma
Current Pharmaceutical Design Malignant Pleural Effusion Evaluation and Management
Current Respiratory Medicine Reviews When Ubiquitin Meets NF-κB: A Trove for Anti-cancer Drug Development
Current Pharmaceutical Design Anticancer Drug Combinations, How Far We can Go Through?
Anti-Cancer Agents in Medicinal Chemistry Exploiting Internal Ribosome Entry Sites in Gene Therapy Vector Design
Current Gene Therapy An HIV-Positive Patient Presenting with Malignant Bone Tumor in Left Tibia Treated with Microwave Ablation for Limb Salvage
Current HIV Research Development of Therapeutics for High Grade Gliomas Using Orthotopic Rodent Models
Current Medicinal Chemistry Anti-Cancer/Anti-Tumor
Current Bioactive Compounds Role of Chemokines and Their Receptors in Cancer
Current Pharmaceutical Design Recombinant Human Serum Albumin Fusion Proteins and Novel Applications in Drug Delivery and Therapy
Current Pharmaceutical Design Ultrasound Imaging of Cervical Anatomic Variants
Current Medical Imaging Gender Disparity in Pediatric Diseases
Current Molecular Medicine Manganese Superoxide Dismutase (Sod2) and Redox-Control of Signaling Events That Drive Metastasis
Anti-Cancer Agents in Medicinal Chemistry Current Drug Targets for Thymic Neoplasms
Current Cancer Drug Targets Synthetic Peptides Derived from the C-Terminal Region of Lys49 Phospholipase A2 Homologues from Viperidae Snake Venoms: Biomimetic Activities and Potential Applications
Current Pharmaceutical Design Deep Penetration of Nanoparticulate Drug Delivery Systems into Tumors: Challenges and Solutions
Current Medicinal Chemistry Natural Sourced Inhibitors of EGFR, PDGFR, FGFR and VEGFRMediated Signaling Pathways as Potential Anticancer Agents
Current Medicinal Chemistry Emerging Immunotargets in Metastatic Renal Cell Carcinoma
Current Drug Targets Editorial
Current Medical Imaging