Abstract
Scutellarin (1) possesses distinguished efficacy in the clinical therapy of cerebral infarction, coronary heart disease, and angina pectoris. Scutellarin (1) is readily converted in vivo, therefore, synthetic methods for the construction of its metabolites will be very important in the near future. In this work, an efficient and first synthetic method for 6-O-methyl- scutellarein (3), one metabolite of scutellarin in vivo, is developed. Dichlorodiphenylmethane in diphenyl ether is used firstly to protect the dihydroxy groups at C-6 and C-7 in scutellarein (2). Then, benzyl bromide is used to selectively protect the hydroxy groups at C-4' and C-7 in 10. 6-O-Methyl-scutellarein (3) is obtained in high yield through seven steps.
Keywords: 6-O-methyl-scutellarein, metabolite, scutellarin, synthesis, regioselective protection.
Letters in Organic Chemistry
Title:Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation
Volume: 10 Issue: 10
Author(s): Min-Zhe Shen, Zhi-Hao Shi, Nian-Guang Li, Hao -Tang, Qian-Ping Shi, Yu-Ping Tang, Jian-Ping Yang and Jin-Ao Duan
Affiliation:
Keywords: 6-O-methyl-scutellarein, metabolite, scutellarin, synthesis, regioselective protection.
Abstract: Scutellarin (1) possesses distinguished efficacy in the clinical therapy of cerebral infarction, coronary heart disease, and angina pectoris. Scutellarin (1) is readily converted in vivo, therefore, synthetic methods for the construction of its metabolites will be very important in the near future. In this work, an efficient and first synthetic method for 6-O-methyl- scutellarein (3), one metabolite of scutellarin in vivo, is developed. Dichlorodiphenylmethane in diphenyl ether is used firstly to protect the dihydroxy groups at C-6 and C-7 in scutellarein (2). Then, benzyl bromide is used to selectively protect the hydroxy groups at C-4' and C-7 in 10. 6-O-Methyl-scutellarein (3) is obtained in high yield through seven steps.
Export Options
About this article
Cite this article as:
Shen Min-Zhe, Shi Zhi-Hao, Li Nian-Guang, -Tang Hao, Shi Qian-Ping, Tang Yu-Ping, Yang Jian-Ping and Duan Jin-Ao, Efficient Synthesis of 6-O-methyl-scutellarein from Scutellarin via Selective Methylation, Letters in Organic Chemistry 2013; 10 (10) . https://dx.doi.org/10.2174/15701786113109990046
DOI https://dx.doi.org/10.2174/15701786113109990046 |
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
-
From Diabetes to Metabolic Syndrome: A View Point on An Evolving Concept
Current Pharmaceutical Design Pleiotropic Effects of HDL: Towards New Therapeutic Areas for HDL-Targeted Interventions
Current Molecular Medicine Rhodanine as a Privileged Scaffold in Drug Discovery
Current Medicinal Chemistry Mechanical Design and Control Method for SEA and VSA-based Exoskeleton Devices for Elbow Joint Rehabilitation
Neuroscience and Biomedical Engineering (Discontinued) Mutations of Nuclear and Mitochondrial Genomes as Potential Targets for the Treatment of Metabolic Syndrome
Current Pharmaceutical Design Dyslipidemia as a Risk Factor for Erectile Dysfunction
Current Medicinal Chemistry Investigation of Chemical Compounds, Antioxidant and Antimicrobial Properties of Teucrium arduini L. (Lamiaceae)
Current Drug Targets The Hydrocarbon Staple & Beyond: Recent Advances Towards Stapled Peptide Therapeutics that Target Protein-Protein Interactions
Current Topics in Medicinal Chemistry Blood-based Biomarkers of Alzheimer’s Disease: The Long and Winding Road
Current Pharmaceutical Design A Comprehensive Review on the Biological and Pharmacological Activities of Rhodanine Based Compounds for Research and Development of Drugs
Mini-Reviews in Medicinal Chemistry Retinal Vascular Features for Cardio Vascular Disease Prediction: A Review
Recent Patents on Computer Science Maternal Sepsis 2010: Early Recognition and Aggressive Treatment with Early Goal Directed Therapy can Improve Maternal Outcomes
Current Women`s Health Reviews Mesenchymal Stem Cells: New Approaches for the Treatment of Neurological Diseases
Current Stem Cell Research & Therapy Hypertension and Diabetes: Emphasis on the Renin-Angiotensin System in Atherosclerosis
Current Hypertension Reviews Editorial [Hot topic: New Developments in the Treatment and Prevention of Vascular Disease - Part 1 (Executive Editors: N. Katsiki, V.G. Athyros and D.P. Mikhailidis)]
Current Pharmaceutical Design Management of Cardiogenic Shock due to Thyrotoxicosis: A Systematic Literature Review
Current Cardiology Reviews Modulation of Angiogenesis for Cancer Prevention: Strategies Based On Antioxidants and Copper Deficiency
Current Pharmaceutical Design The Right Ventricle: Biologic Insights and Response to Disease: Updated
Current Cardiology Reviews Recent Developments in the Synthesis of Acetylcholinesterase Inhibitors
Mini-Reviews in Medicinal Chemistry CD93: Recent Advances and Implications in Disease
Current Drug Targets