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
-
Chemotherapy for Prostate Cancer
Current Pharmaceutical Design Tangy Scent in Toona sinensis (Meliaceae) Leaflets: Isolation, Functional Characterization, and Regulation of TsTPS1 and TsTPS2, Two Key Terpene Synthase Genes in the Biosynthesis of the Scent Compound
Current Pharmaceutical Biotechnology Anti-Inflammatory Activities of Some Bee Products by Inhibition of Bovine Testes Hyaluronidase
Current Enzyme Inhibition A Review of Lysergic Acid Diethylamide (LSD) in the Treatment of Addictions: Historical Perspectives and Future Prospects
Current Drug Abuse Reviews Quantitative Structure-activity Relationships of Imidazole-containing Farnesyltransferase Inhibitors Using Different Chemometric Methods
Medicinal Chemistry Isolation and Structural Elucidation of Antioxidant Peptides from Oyster (Saccostrea cucullata) Protein Hydrolysate
Protein & Peptide Letters Sorafenib (BAY 43-9006) in Hepatocellular Carcinoma Patients: From Discovery to Clinical Development
Current Medicinal Chemistry Inpatient Care of the HIV Infected Patient in the Highly Active Antiretroviral Therapy (HAART) Era
Current HIV Research Molecular Pathology and Molecular Markers of Ductal Carcinoma in-situ
Current Cancer Therapy Reviews Opto-Acoustic Imaging of Drug Discovery Biomarkers
Current Pharmaceutical Biotechnology Network Pharmacology: Reigning in Drug Attrition?
Current Drug Discovery Technologies Withdrawal Notice: Role of Zinc Oxide Nanoparticles Synthesized by Fenugreek Seeds Extract as Anticancer Agent: In Vitro and In Vivo Studies
Anti-Cancer Agents in Medicinal Chemistry Comparison of Two Types of Amino Acid Solutions on <sup>177</sup>Lu-Dotatate Pharmacokinetics and Pharmacodynamics in Patients with Metastatic Gastroenteropancreatic Neuroendocrine Tumors
Current Radiopharmaceuticals Exploring the Phosphoproteome with Mass Spectrometry
Mini-Reviews in Medicinal Chemistry Hydroxytyrosol and Derivatives: Isolation, Synthesis, and Biological Properties
Current Organic Chemistry Use of Metallomics in Environmental Pollution Assessment Using Mice Mus musculus/Mus spretus as Bioindicators
Current Analytical Chemistry Circulating Nucleic Acids in Plasma and Serum: Roles in Diagnosis and Prognosis in Diabetes and Cancer
Infectious Disorders - Drug Targets Recent Advancement in Topical Drug Delivery for Psoriasis: Clinical Pertinence and Potential Market
Current Drug Targets Novel Biomarkers Assessing the Calcium Deposition in Coronary Artery Disease
Current Medicinal Chemistry Phytochemicals for Drug Discovery in Alzheimer’s Disease: <i>In Silico</i> Advances
Current Pharmaceutical Design