Abstract
Cancer is a serious worldwide health threat, killing almost seven million people per year. Quinones are an important class of antitumour agents that are activated by tumour hypoxia. Primin (2-methoxy-6-n-pentyl-1,4-benzoquinone), a naturally-occurring product obtained from Primula obconica (Primulaceae) has shown antimicrobial and antitumour properties. The synthesis of the Primin to obtain 3-, 5- or 6-alkyl substituted derivatives has been previously attempted seeking antitumour activity. The intermediate reaction products, 2-methoxy-hydroquinone-di-(2-tetrahydropyranyl) ether and 2-methoxy-6-n-pentyl-hydroquinone-di-(2-tetrahydropyranyl) ether were obtained and evaluated against sarcoma 180 (S-180) and Ehrlich carcinoma, as well as toxicity tests were performed. The antitumour activity tests showed that these intermediate compounds were able to inhibit S-180 sarcoma and Ehrlich carcinoma growth in mice. These results indicated that the tetrahydropyranyl protect group conserved the antitumour activity in comparison with quinone group, however, it exhibited a less toxic effect, with no characteristic of quinones. These results can suggest that compound 2-methoxy-6-n-pentyl-hydroquinone-di-(2-tetrahydropyranyl) ether may act as a prodrug with some advantages in comparison with the Primin.
Keywords: Primin derivative, benzoquinone, antitumour agent, prodrug
Medicinal Chemistry
Title: Synthesis and Antitumour Activity of the Primin (2-methoxy-6-n-pentyl-1,4-benzoquinone) and Analogues
Volume: 3 Issue: 4
Author(s): D.J. Brondani, C.R.M. Nascimento, D.R. de M. Moreira, A.C. Lima Leite, I.A. de Souza and L.W. Bieber
Affiliation:
Keywords: Primin derivative, benzoquinone, antitumour agent, prodrug
Abstract: Cancer is a serious worldwide health threat, killing almost seven million people per year. Quinones are an important class of antitumour agents that are activated by tumour hypoxia. Primin (2-methoxy-6-n-pentyl-1,4-benzoquinone), a naturally-occurring product obtained from Primula obconica (Primulaceae) has shown antimicrobial and antitumour properties. The synthesis of the Primin to obtain 3-, 5- or 6-alkyl substituted derivatives has been previously attempted seeking antitumour activity. The intermediate reaction products, 2-methoxy-hydroquinone-di-(2-tetrahydropyranyl) ether and 2-methoxy-6-n-pentyl-hydroquinone-di-(2-tetrahydropyranyl) ether were obtained and evaluated against sarcoma 180 (S-180) and Ehrlich carcinoma, as well as toxicity tests were performed. The antitumour activity tests showed that these intermediate compounds were able to inhibit S-180 sarcoma and Ehrlich carcinoma growth in mice. These results indicated that the tetrahydropyranyl protect group conserved the antitumour activity in comparison with quinone group, however, it exhibited a less toxic effect, with no characteristic of quinones. These results can suggest that compound 2-methoxy-6-n-pentyl-hydroquinone-di-(2-tetrahydropyranyl) ether may act as a prodrug with some advantages in comparison with the Primin.
Export Options
About this article
Cite this article as:
D.J. Brondani , C.R.M. Nascimento , D.R. de M. Moreira , A.C. Lima Leite , I.A. de Souza and L.W. Bieber , Synthesis and Antitumour Activity of the Primin (2-methoxy-6-n-pentyl-1,4-benzoquinone) and Analogues, Medicinal Chemistry 2007; 3 (4) . https://dx.doi.org/10.2174/157340607781024410
DOI https://dx.doi.org/10.2174/157340607781024410 |
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
-
Pattern of Care for Skin Cancers - Canada and France
Current Cancer Therapy Reviews Review of Structures Containing Fullerene-C60 for Delivery of Antibacterial Agents. Multitasking model for Computational Assessment of Safety Profiles
Current Bioinformatics TRPV1: On the Road to Pain Relief
Current Molecular Pharmacology Targeting Death Receptors to Fight Cancer: From Biological Rational to Clinical Implementation
Current Medicinal Chemistry Interaction of ABC Multidrug Transporters with Anticancer Protein Kinase Inhibitors: Substrates and/or Inhibitors?
Current Cancer Drug Targets Transcriptional Analysis of JAK/STAT Signaling in Glioblastoma Multiforme
Current Pharmacogenomics and Personalized Medicine Targeting the Tumor Stroma with Peroxisome Proliferator Activated Receptor (PPAR) Agonists
Anti-Cancer Agents in Medicinal Chemistry Development of Therapeutics for High Grade Gliomas Using Orthotopic Rodent Models
Current Medicinal Chemistry Therapeutic Potential of γ -Secretase Inhibitors and Modulators
Current Topics in Medicinal Chemistry Oncologic Imaging End-Points for the Assessment of Therapy Response
Recent Patents on Anti-Cancer Drug Discovery Peptide-Mediated Delivery of Therapeutic and Imaging Agents Into Mammalian Cells
Current Pharmaceutical Design Upregulation of Focal Adhesion Kinase by 14-3-3ε via NFκB Activation in Hepatocellular Carcinoma
Anti-Cancer Agents in Medicinal Chemistry Hypoxia-inducible Factor (HIF) in Hormone Signaling During Health and Disease
Cardiovascular & Hematological Agents in Medicinal Chemistry Comparison of Uptake Mechanisms for Anthracyclines in Human Leukemic Cells
Current Drug Delivery Anti-Angiogenic Peptides for Cancer Therapeutics
Current Pharmaceutical Biotechnology Clinical Experiment of Mutant Herpes Simplex Virus HF10 Therapy for Cancer
Current Cancer Drug Targets MicroRNA as Regulators of Cancer Stem Cells and Chemoresistance in Colorectal Cancer
Current Cancer Drug Targets Gene Therapy (Part II)
Current Gene Therapy The NGF Metabolic Pathway in the CNS and its Dysregulation in Down Syndrome and Alzheimer’s Disease
Current Alzheimer Research KRAS: A Promising Therapeutic Target for Cancer Treatment
Current Topics in Medicinal Chemistry