Abstract
A series of 2-methyl-N-substituted-benzimidazoles, bearing hydroxypyrrolidinon-5-yl or hydroxypyrrolidin-2- yl, 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside, 2,3,5,6-tetrahydroxy-α-D-mannofuranoside, 1:2,5:6-di-O-isopropylidene- α-D-gluco-furanose,3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-α-D-xylo-heptofuranos-5-ulose, 3-O-benzyl- 6,7-dideoxy-1,2-dihydroxy-α-D-xylo-heptofuranos-5-ulose, 1,2,5,6-tetrahydroxy-α-D-glucofuranose sugar moieties, were obtained in good yields from 2-methyl N-(trichloroacetamidomethyl)benzimidazole as a donor and carbohydrate residues as acceptor precursors in the presence of catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as Lewis acid. Compounds 6, 7, 10, 13, 15, and 16 showed significant anti-inflammatory and analgesic activities.
Keywords: Benzimidazole, trichloroacetimidate, imidomethylation, anti-inflammatory, analgesic
Medicinal Chemistry
Title: Structure-Based Design of Benzimidazole Sugar Conjugates: Synthesis, SAR and In Vivo Anti-inflammatory and Analgesic Activities
Volume: 5 Issue: 6
Author(s): Ahmed O.H. El-Nezhawy, Samir T. Gaballah, Mohamed A.A. Radwan, Ayman R. Baiuomy and Omar M.E. Abdel-Salam
Affiliation:
Keywords: Benzimidazole, trichloroacetimidate, imidomethylation, anti-inflammatory, analgesic
Abstract: A series of 2-methyl-N-substituted-benzimidazoles, bearing hydroxypyrrolidinon-5-yl or hydroxypyrrolidin-2- yl, 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside, 2,3,5,6-tetrahydroxy-α-D-mannofuranoside, 1:2,5:6-di-O-isopropylidene- α-D-gluco-furanose,3-O-benzyl-6,7-dideoxy-1:2-O-isopropylidene-α-D-xylo-heptofuranos-5-ulose, 3-O-benzyl- 6,7-dideoxy-1,2-dihydroxy-α-D-xylo-heptofuranos-5-ulose, 1,2,5,6-tetrahydroxy-α-D-glucofuranose sugar moieties, were obtained in good yields from 2-methyl N-(trichloroacetamidomethyl)benzimidazole as a donor and carbohydrate residues as acceptor precursors in the presence of catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as Lewis acid. Compounds 6, 7, 10, 13, 15, and 16 showed significant anti-inflammatory and analgesic activities.
Export Options
About this article
Cite this article as:
El-Nezhawy O.H. Ahmed, Gaballah T. Samir, Radwan A.A. Mohamed, Baiuomy R. Ayman and Abdel-Salam M.E. Omar, Structure-Based Design of Benzimidazole Sugar Conjugates: Synthesis, SAR and In Vivo Anti-inflammatory and Analgesic Activities, Medicinal Chemistry 2009; 5 (6) . https://dx.doi.org/10.2174/157340609790170461
DOI https://dx.doi.org/10.2174/157340609790170461 |
Print ISSN 1573-4064 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6638 |
Call for Papers in Thematic Issues
Carbohydrates in Computational and Medicinal Chemistry
Carbohydrates are the most essential organic molecules and are involved in the maintenance of various physiological and metabolic processes in living organisms. Carbohydrate-based compounds have come to the attention of researchers because of their significant contributions to biological functions, such as cell development and cell proliferation, connections between several cells, ...read more
Recent Advances in the Medicinal Chemistry of Cancer
Scope of the Thematic Issue: Correlation between structure and function is one of the important aspects of the success of anti-cancer compounds associated with their structure-activity interactions, physiology, biochemical, molecular, and genetic processes. Overcoming these obstacles is key to obtaining further insights into developments in rational drug design, bioorganic chemistry, ...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
Related Articles
-
Therapeutic Application of Histone Deacetylase Inhibitors for Stroke
Central Nervous System Agents in Medicinal Chemistry Berberine Exerts Anti-cancer Activity by Modulating Adenosine Monophosphate- Activated Protein Kinase (AMPK) and the Phosphatidylinositol 3-Kinase/ Protein Kinase B (PI3K/AKT) Signaling Pathways
Current Pharmaceutical Design Cell-penetrating Peptides for Cancer-targeting Therapy and Imaging
Current Cancer Drug Targets Adhesion Mechanisms of the Lyme Disease Spirochete, Borrelia burgdorferi
Current Drug Targets - Infectious Disorders Antineoplastic Potential of Medicinal Plants
Recent Patents on Biotechnology Nonsynaptic Receptors for GABA and Glutamate
Current Topics in Medicinal Chemistry The Use of Anthracyclines for Therapy of CNS Tumors
Anti-Cancer Agents in Medicinal Chemistry Role of NF-κB and NF-κB-regulated Gene Products in Chemoresistance and Radioresistance
Current Cancer Therapy Reviews Carbohydrates: Potential Sweet Tools Against Cancer
Current Medicinal Chemistry The Arrestin Fold: Variations on a Theme
Current Genomics CYP4 Enzymes As Potential Drug Targets: Focus on Enzyme Multiplicity, Inducers and Inhibitors, and Therapeutic Modulation of 20- Hydroxyeicosatetraenoic Acid (20-HETE) Synthase and Fatty Acid ω- Hydroxylase Activities
Current Topics in Medicinal Chemistry Yttrium-90 – Current Status, Expected Availability and Applications of a High Beta Energy Emitter
Current Radiopharmaceuticals Non Polymeric Nanoparticles for Photodynamic Therapy Applications: Recent Developments
Current Medicinal Chemistry Circulating Tumor Stem Cells as Biomarkers for Cancer Progression
Recent Patents on Biomarkers Vascularization of Biomaterials for Bone Tissue Engineering: Current Approaches and Major Challenges
Current Angiogenesis (Discontinued) The Inverse Relationship Between Cancer and Alzheimer's Disease: A Possible Mechanism
Current Alzheimer Research Poxvirus Cancer Therapy
Recent Patents on Anti-Infective Drug Discovery Recent Developments in Anti-Cancer Agents Targeting the Ras/Raf/ MEK/ERK Pathway
Recent Patents on Anti-Cancer Drug Discovery The Emerging Role of Stereotactic Radiosurgery in the Treatment of Glioblastoma Multiforme
Current Radiopharmaceuticals Flavonoids as Anticancer Agents: Recent Progress and State of the Art?
Current Organic Chemistry