Abstract
(5Z,9Z)-11-Phenylundeca-5,9-dienoic acid was stereoselectively synthesized, based on original cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and buta-2,3-dien-1-ylbenzene with EtMgBr in the presence of the Cp2TiCl2 catalyst giving 2,5-dialkylydenemagnesacyclopentane in 86% yield. The acid hydrolysis of the product and Jones oxidation of the resulting 2-{[(5Z,9Z)-11-phenylundeca-5,9-dien-1-yl]oxy}tetrahydro-2Н-pyran afforded (5Z,9Z)-11-phenylundeca-5,9-dienoic acid in an overall yield of 75%. A high inhibitory activity of the synthesized acid with respect to human topoisomerase I (hTop1) and II (hTop2α) was detected. Resorting to the data of molecular docking, a mechanism of inhibition was proposed.
Keywords: Cyclomagnesiation, docking, fatty acids, homogeneous catalysis, novel topoisomerase I and IIα inhibitors, stereoselective synthesis of 5Z, 9Z-dienoic acid.
Current Cancer Drug Targets
Title:11-Phenylundeca-5Z,9Z-dienoic Acid: Stereoselective Synthesis and Dual Topoisomerase I/IIα Inhibition
Volume: 15 Issue: 6
Author(s): Vladimir A. D’yakonov, Lilya U. Dzhemileva, Aleksey A. Makarov, Alfiya R. Mulyukova, Dmitry S. Baevd, Elza K. Khusnutdinova, Tatiana G. Tolstikova and Usein M. Dzhemilev
Affiliation:
Keywords: Cyclomagnesiation, docking, fatty acids, homogeneous catalysis, novel topoisomerase I and IIα inhibitors, stereoselective synthesis of 5Z, 9Z-dienoic acid.
Abstract: (5Z,9Z)-11-Phenylundeca-5,9-dienoic acid was stereoselectively synthesized, based on original cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and buta-2,3-dien-1-ylbenzene with EtMgBr in the presence of the Cp2TiCl2 catalyst giving 2,5-dialkylydenemagnesacyclopentane in 86% yield. The acid hydrolysis of the product and Jones oxidation of the resulting 2-{[(5Z,9Z)-11-phenylundeca-5,9-dien-1-yl]oxy}tetrahydro-2Н-pyran afforded (5Z,9Z)-11-phenylundeca-5,9-dienoic acid in an overall yield of 75%. A high inhibitory activity of the synthesized acid with respect to human topoisomerase I (hTop1) and II (hTop2α) was detected. Resorting to the data of molecular docking, a mechanism of inhibition was proposed.
Export Options
About this article
Cite this article as:
D’yakonov Vladimir A., Dzhemileva Lilya U., Makarov Aleksey A., Mulyukova Alfiya R., S. Baevd Dmitry, Khusnutdinova Elza K., Tolstikova Tatiana G. and Dzhemilev Usein M., 11-Phenylundeca-5Z,9Z-dienoic Acid: Stereoselective Synthesis and Dual Topoisomerase I/IIα Inhibition , Current Cancer Drug Targets 2015; 15 (6) . https://dx.doi.org/10.2174/1568009615666150506093155
DOI https://dx.doi.org/10.2174/1568009615666150506093155 |
Print ISSN 1568-0096 |
Publisher Name Bentham Science Publisher |
Online ISSN 1873-5576 |
Call for Papers in Thematic Issues
Advances in Cancer Biomarkers and Potential Drug Targets: From Diagnosis to Therapy
Cancer biomarkers play a crucial role in the diagnosis, prognosis, and treatment of cancer. They provide valuable information for cancer detection, risk assessment, treatment selection, and monitoring response to therapy. With advancements in molecular biology and high-throughput technologies, there has been an increasing interest in identifying and characterizing cancer biomarkers ...read more
Novel Therapeutic Approaches to Target Drug Resistant Tumors
With the development of disciplines such as chemical biology and molecular biology, the genes or proteins closely related to tumor occurrence and development have gradually become clear. Targeted therapies targeting these genes or proteins provide more effective methods for tumor treatment. Tumor targeted drugs generally only act on specific targets ...read more
ROLE OF IMMUNE AND GENOTOXIC RESPONSE BIOMARKERS IN TUMOR MICROENVIRONMENT IN CANCER DIAGNOSIS AND TREATMENT
Biological biomarkers have been used in medical research as an indicator of a normal or abnormal process inside the body, or of a disease. Nowadays, various researchers are in process to explore and investigate the biological markers for the early assessment of cancer. DNA Damage response (DDR) pathways and immune ...read more
Targeting the battlefield between host and tumor: basic research and clinical practice on reshaping tumor immune microenvironment
Immune system protects host against malignant tumors through effector cells and molecules. Cancer development and its response to therapy are regulated by inflammation, which either promotes or suppresses cancer progression. Chronic inflammation facilitates cancer progression and treatment resistance, whereas induction of acute inflammatory reactions often lead to anti-cancer immune responses. ...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
-
A Review of Pharmacological Treatment Options for Lung Cancer: Emphasis on Novel Nanotherapeutics and Associated Toxicity
Current Drug Targets An Overview of Galenic Preparation Methods for Medicinal Cannabis
Current Bioactive Compounds Opiates as Antidepressants
Current Pharmaceutical Design Hereditary Breast Cancer in Sub-Saharan Africa
Current Women`s Health Reviews Formulation and Characterization of Anthocyanins-Loaded Nanoparticles
Current Drug Delivery Oxidatively Generated DNA Lesions as Potential Biomarkers of In Vivo Oxidative Stress
Current Molecular Medicine Current State of Intellectual Property in Microfluidic Nucleic Acid Analysis
Recent Patents on Engineering The Role of NAD+ Dependent Histone Deacetylases (sirtuins) in Ageing
Current Drug Targets Clinical Evaluation of Anti-Obesity Drugs
Current Drug Targets Pisco Bagasse as a Potential Source of Bioactive Compounds – A Review
Recent Patents on Engineering Integrated Differential Regulatory Analysis Reveals a Novel Prognostic 36-Gene Signature for Gastric Cancer in Asian Population
Combinatorial Chemistry & High Throughput Screening The mTOR/4E-BP1/eIF4E Signalling Pathway as a Source of Cancer Drug Targets
Current Medicinal Chemistry Comparison of Luminescence ADP Production Assay and Radiometric Scintillation Proximity Assay for Cdc7 Kinase
Combinatorial Chemistry & High Throughput Screening Advances in DNA Sensing Using BioFETs
Micro and Nanosystems Metabolic Response Assessment in Non-Small Cell Lung Cancer Patients after Platinum-Based Therapy: A Preliminary Analysis
Current Medical Imaging Nuclear Targeting of Gold Nanoparticles for Improved Therapeutics
Current Topics in Medicinal Chemistry Processing and Regulation Mechanisms within Antigen Presenting Cells: A Possibility for Therapeutic Modulation
Current Pharmaceutical Design Structure-Based Virtual Screening for Drug Discovery: Principles, Applications and Recent Advances
Current Topics in Medicinal Chemistry Genetic and Pharmacogenetic Aspects of Alcohol-Dependence
Current Pharmacogenomics Mechanisms of MDMA (Ecstasy)-Induced Oxidative Stress, Mitochondrial Dysfunction, and Organ Damage
Current Pharmaceutical Biotechnology