Abstract
Background: Modified pyrimidines is a very important pharmacophore core of naturally occurring and synthetic bioactive compounds, interacting with the synthesis and function of nucleic acids, interfering with biosynthetic pathways and competing for the same binding sites of naturally occurring pyrimidines.
Method: C5-arylalkynyl glucopyranonucleosides 3, 5 and -3´-C-trifluoromethyl-β-D-allopyranonucleosides of uracil 13, were synthesized using the one-step Sonogashira reaction under microwave irradiation and subsequent deprotection. Hydrogenation of acetylated 2a,e,i,j,k,n with NiCl2 and NaBH4, gave C5-phenylethenyl 6n and C5-arylethyl 8a,e,i,j,k uracil pyranonucleosides, which upon deacetylation, afforded the unprotected pyranonucleosides 7n and 9a,e,i,j,k, respectively.
Results: The newly synthesized compounds were evaluated for their potential cytostatic activities in cell culture.
Conclusion: The results of the cytostatic examinations indicated that compounds 2a,e,i,j and 12c,d are suitable candidates for further biological studies on lead drug and structural optimization.
Keywords: C5-pyrimidine pyranonucleosides, cytotoxic activity, microwave irradiation, sonogashira reaction, synthesized compounds, synthetic.
Current Microwave Chemistry
Title:Facile Microwave-assisted Synthesis of Various C5-modified Pyrimidine Pyranonucleosides as Potential Cytotoxic Antitumor Agents
Volume: 4 Issue: 4
Author(s): Athina Dimopoulou, Nikolaos Kollatos, Stella Manta, Aggeliki Panagiotopoulou, Athanasios Karastergiou, Filitsa Kontopoulou, Dominique Schols and Dimitri Komiotis*
Affiliation:
- Department of Biochemistry and Biotechnology, Laboratory of Bioorganic Chemistry, University of Thessaly, Viopolis, Larissa,Greece
Keywords: C5-pyrimidine pyranonucleosides, cytotoxic activity, microwave irradiation, sonogashira reaction, synthesized compounds, synthetic.
Abstract: Background: Modified pyrimidines is a very important pharmacophore core of naturally occurring and synthetic bioactive compounds, interacting with the synthesis and function of nucleic acids, interfering with biosynthetic pathways and competing for the same binding sites of naturally occurring pyrimidines.
Method: C5-arylalkynyl glucopyranonucleosides 3, 5 and -3´-C-trifluoromethyl-β-D-allopyranonucleosides of uracil 13, were synthesized using the one-step Sonogashira reaction under microwave irradiation and subsequent deprotection. Hydrogenation of acetylated 2a,e,i,j,k,n with NiCl2 and NaBH4, gave C5-phenylethenyl 6n and C5-arylethyl 8a,e,i,j,k uracil pyranonucleosides, which upon deacetylation, afforded the unprotected pyranonucleosides 7n and 9a,e,i,j,k, respectively.
Results: The newly synthesized compounds were evaluated for their potential cytostatic activities in cell culture.
Conclusion: The results of the cytostatic examinations indicated that compounds 2a,e,i,j and 12c,d are suitable candidates for further biological studies on lead drug and structural optimization.
Export Options
About this article
Cite this article as:
Dimopoulou Athina , Kollatos Nikolaos , Manta Stella , Panagiotopoulou Aggeliki , Karastergiou Athanasios , Kontopoulou Filitsa , Schols Dominique and Komiotis Dimitri *, Facile Microwave-assisted Synthesis of Various C5-modified Pyrimidine Pyranonucleosides as Potential Cytotoxic Antitumor Agents, Current Microwave Chemistry 2017; 4 (4) . https://dx.doi.org/10.2174/2213335604666170720151941
DOI https://dx.doi.org/10.2174/2213335604666170720151941 |
Print ISSN 2213-3356 |
Publisher Name Bentham Science Publisher |
Online ISSN 2213-3364 |
Call for Papers in Thematic Issues
Advance in Drug Delivery Carrier Microwave-Assisted Reactions for Enhanced Therapeutics and Diagnostic Purposes
Microwave irradiation technology has numerous applications in organic synthesis, pharmaceuticals, and the development of nanocarriers. To date, microwave-assisted reactions have garnered significant attention in synthesizing drug delivery carriers. Considering the advantages of microwave-assisted reactions, such as high percentage yield, shorter reaction time, and compound purity; microwave-assisted technology holds promise in ...read more
Microwave Technology: Advancements and Applications in Chemistry, Environment and Food Science
Microwave technology has emerged as a transformative tool in various fields, offering unique opportunities for rapid, efficient, and clean processes. This thematic issue aims to encapsulate the latest research, innovative strategies, and progressive methodologies concerning the application of microwave technology in three main areas: Chemistry: Highlighting the advancements in microwave-assisted ...read more
Related Journals
![](/images/wayfinder.jpg)
- 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
-
The Synthesis and Anticancer Potentials of Quinoline Analogues: A Review of Literature
Mini-Reviews in Organic Chemistry Histone Deacetylase Inhibitors: New Promise in the Treatment of Immune and Inflammatory Diseases
Current Drug Targets Protein-protein Interactions: Network Analysis and Applications in Drug Discovery
Current Pharmaceutical Design Colloidal Supramolecular Aggregates for Therapeutic Application in Neuromedicine
Current Medicinal Chemistry [BMIM][[HSO4]: An Efficient and Green Promoter for the Synthesis of 5H-benzo[a]phenothiazine Derivatives
Current Catalysis The Immunohistochemical Assessment of HPV Related Adenocarcinoma: Pathologic and Clinical Prognostic Significance
Current Pharmaceutical Design UPLC-MS Metabonomics Reveals Perturbed Metabolites in HIV-Infected Sera
Current Metabolomics Osteogenic Differentiation Factors of Multipotent Mesenchymal Stromal Cells in the Current Understanding
Current Pharmaceutical Design Molecular Mechanism of Aniline Induced Spleen Toxicity and Neuron Toxicity in Experimental Rat Exposure: A Review
Current Neuropharmacology Breakthrough Pain
Current Drug Therapy An Active and Low-cost Microwave Imaging System for Detection of Breast Cancer Using Back Scattered Signal
Current Medical Imaging Electrochemical Protein-based Bioanalytical Devices for Drug Analysis
Current Topics in Medicinal Chemistry Effect of Thawing Conditions on Polyphenol Content and Antioxidant Activity of Frozen Haskap Berries (<i>Lonicera caerulea L.</i>)
Current Nutrition & Food Science Recent Advances in the Methodology and Application for the Metabolism of Phytochemical Compounds-An Update Covering the Period of 2009-2014
Current Drug Metabolism Molecular Basis for the Neuroprotective Properties of FKBP-Binding Immunophilin Ligands
Current Medicinal Chemistry - Central Nervous System Agents Bioinformatics Approach in Plant Genomic Research
Current Genomics Realizing the Potential of Health-Promoting Rosehips from Dogroses (Rosa sect. Caninae)
Current Bioactive Compounds Metalloprotein Inhibitors for the Treatment of Human Diseases
Current Topics in Medicinal Chemistry (1→3)-α-D-Glucans from Aspergillus spp.: Structural Characterization and Biological Study on their Carboxymethylated Derivatives
Current Drug Targets Involvement of Endoplasmic Reticulum Stress in Isoliquiritigenin-Induced SKOV-3 Cell Apoptosis
Recent Patents on Anti-Cancer Drug Discovery