Abstract
This work describes cheap and simple methods to obtain biological active furano naphthoquinones in good yields. Hydroxyiso-β-lapachone (3) was obtained in 61% yield from the reaction of lapachol (1) and MCPBA in dichloromethane using Na2HPO4 as the base. Reaction of 1 with MCPBA, followed by the addition of KOH/DMSO furnished both stenocarpoquinone-A (2) and avicequinone-C (5) in 20% yield. Using oxone/acetone and NaHCO3, stenocarpoquinone-B (4) was obtained in 50% yield. The biological assays using tumor cell lines showed that 1 is, in general, less toxic than its derivatives. Compounds 4 and 5, on the other hand, were strongly active against the four tested tumor cells.
Keywords: Lapachol, natural naphthoquinones, cyclization reactions, anticancer, antibacterial, antimalarial, antifungal, antileishmanial, molluscicidal, antivirus
Letters in Organic Chemistry
Title: Natural Furano Naphtoquinones from Lapachol: Hydroxyiso-β -Lapachone, Stenocarpoquinone-B and Avicequinone-C
Volume: 8 Issue: 5
Author(s): Carlos Magno R. Ribeiro, Pablo P. de Souza, L. D.M. Ferreira, Sharlene L. Pereira, Ingrid da S. Martins, Rosangela de A. Epifanio, Leticia V. Costa-Lotufo, Paula C. Jimenez, Claudia Pessoa and Manoel O. de Moraes
Affiliation:
Keywords: Lapachol, natural naphthoquinones, cyclization reactions, anticancer, antibacterial, antimalarial, antifungal, antileishmanial, molluscicidal, antivirus
Abstract: This work describes cheap and simple methods to obtain biological active furano naphthoquinones in good yields. Hydroxyiso-β-lapachone (3) was obtained in 61% yield from the reaction of lapachol (1) and MCPBA in dichloromethane using Na2HPO4 as the base. Reaction of 1 with MCPBA, followed by the addition of KOH/DMSO furnished both stenocarpoquinone-A (2) and avicequinone-C (5) in 20% yield. Using oxone/acetone and NaHCO3, stenocarpoquinone-B (4) was obtained in 50% yield. The biological assays using tumor cell lines showed that 1 is, in general, less toxic than its derivatives. Compounds 4 and 5, on the other hand, were strongly active against the four tested tumor cells.
Export Options
About this article
Cite this article as:
Magno R. Ribeiro Carlos, P. de Souza Pablo, D.M. Ferreira L., L. Pereira Sharlene, da S. Martins Ingrid, de A. Epifanio Rosangela, V. Costa-Lotufo Leticia, C. Jimenez Paula, Pessoa Claudia and O. de Moraes Manoel, Natural Furano Naphtoquinones from Lapachol: Hydroxyiso-β -Lapachone, Stenocarpoquinone-B and Avicequinone-C, Letters in Organic Chemistry 2011; 8 (5) . https://dx.doi.org/10.2174/157017811795685063
DOI https://dx.doi.org/10.2174/157017811795685063 |
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
-
Development of Yeast Molecular Display Systems Focused on Therapeutic Proteins, Enzymes, and Foods: Functional Analysis of Proteins and its Application to Bioconversion
Recent Patents on Biotechnology Silimarin and Cancer
Anti-Cancer Agents in Medicinal Chemistry Monitoring of Environmental Metals in Human Blood: The Need for Data Validation
Current Analytical Chemistry Chromatin Structure and Epigenetics of Tumour Cells: A Review
Cardiovascular & Hematological Disorders-Drug Targets Therapeutic Vaccines for Cervical Cancer: Dendritic Cell-Based Immunotherapy
Current Pharmaceutical Design Chiral Separation of Several Flavanones by Liquid Chromatography
Current Pharmaceutical Analysis Machine Intelligence Techniques for the Identification and Diagnosis of COVID-19
Current Medicinal Chemistry Genetic Manipulation to Increase Lipase Production in Microorganisms – A Recent Review
Current Biochemical Engineering (Discontinued) Hydrogen Sulfide: A New Tool to Design and Develop Drugs
Clinical Anti-Inflammatory & Anti-Allergy Drugs (Discontinued) High-Content Screening and Mechanism-Based Evaluation of Estrogenic Botanical Extracts
Combinatorial Chemistry & High Throughput Screening The Interest of Folic Acid in Targeted Photodynamic Therapy
Current Medicinal Chemistry Probiotics/Prebiotics in Viral Respiratory Infections: Implication for Emerging Pathogens
Recent Patents on Biotechnology Prevention and Therapy of Prostate Cancer: An Update on Alternatives for Treatment and Future Perspectives
Current Drug Therapy Repurposing of Benzimidazole Scaffolds for HER2 Positive Breast Cancer Therapy: An <i>In-Silico</i> Approach
Current Drug Research Reviews LipoSVM: Prediction of Lysine lipoylation in Proteins based on the Support Vector Machine
Current Genomics Coupling of Conjugating Enzymes and Efflux Transporters: Impact on Bioavailability and Drug Interactions
Current Drug Metabolism Molecular Beacon Aptamers for Protein Monitoring in Real-Time and in Homogeneous Solutions
Current Proteomics Lipid Mediator Profiling in Pulmonary Disease
Current Pharmaceutical Biotechnology A Facile “Click Chemistry” Approach to Novel Flavonol Glycoconjugates and Their Cytotoxic Activity
Letters in Organic Chemistry Synthesis, EGFR Inhibition and Anti-cancer Activity of New 3,6-dimethyl-1-phenyl-4-(substituted-methoxy)pyrazolo[3,4-d] pyrimidine Derivatives
Anti-Cancer Agents in Medicinal Chemistry