Abstract
The spirostanic side chain of pennogenin can be quantitatively transformed under mild acidic conditions in a 22-oxocholestanic framework through a one step procedure. This methodology is the shortest way to afford the 3,16,26- trihydroxy-22-oxocholestanic derivative, analogue of the protected aglycon of the potent antitumor agent OSW-1. The primary hydroxyl group at C-26 could be selectively transformed.
Keywords: Acetolysis, extraction, OSW-1, pennogenin, sapogenin side chain, spirostan, saponins, cardiovascular, gastrointestinal, hydroxysapogenin
Letters in Organic Chemistry
Title: Synthesis of (25R)-17α-Hydroxy-22-oxocholest-5-ene-3β,16β,26-triyl Triacetate: A One-Pot Approach to the Protected Aglycon Analogue of OSW-1
Volume: 8 Issue: 5
Author(s): Maria A. Fernandez-Herrera, Ma. G. Hernandez-Linares, Gabriel Guerrero-Luna, Socorro Meza-Reyesa, Sara Montiel-Smith and Jesus Sandoval-Ramirez
Affiliation:
Keywords: Acetolysis, extraction, OSW-1, pennogenin, sapogenin side chain, spirostan, saponins, cardiovascular, gastrointestinal, hydroxysapogenin
Abstract: The spirostanic side chain of pennogenin can be quantitatively transformed under mild acidic conditions in a 22-oxocholestanic framework through a one step procedure. This methodology is the shortest way to afford the 3,16,26- trihydroxy-22-oxocholestanic derivative, analogue of the protected aglycon of the potent antitumor agent OSW-1. The primary hydroxyl group at C-26 could be selectively transformed.
Export Options
About this article
Cite this article as:
A. Fernandez-Herrera Maria, G. Hernandez-Linares Ma., Guerrero-Luna Gabriel, Meza-Reyesa Socorro, Montiel-Smith Sara and Sandoval-Ramirez Jesus, Synthesis of (25R)-17α-Hydroxy-22-oxocholest-5-ene-3β,16β,26-triyl Triacetate: A One-Pot Approach to the Protected Aglycon Analogue of OSW-1, Letters in Organic Chemistry 2011; 8 (5) . https://dx.doi.org/10.2174/157017811795685018
DOI https://dx.doi.org/10.2174/157017811795685018 |
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
-
Edible Transgenic Plant Vaccines for Different Diseases
Current Pharmaceutical Biotechnology Developments in High-Yield System Expressed Vaccines and Immunotherapy
Recent Patents on Biotechnology Antimutagenic, Antiproliferative and Antioxidant Properties of Sea Grape Leaf Extract Fractions (<i>Coccoloba uvifera</i> L.)
Anti-Cancer Agents in Medicinal Chemistry Chest Pain in Children
Current Pediatric Reviews Targeting the Cancer-Stroma Interaction: A Potential Approach for Pancreatic Cancer Treatment
Current Pharmaceutical Design In vivo Monitoring of Oxygen Levels in Human Brain Tumor Between Fractionated Radiotherapy Using Oxygen-enhanced MR Imaging
Current Medical Imaging Dantrolene Potentiates the Antineoplastic Effect of Sorafenib in Hepatocellular Carcinoma via Targeting Ca<sup>+2</sup>/PI3K Signaling Pathway
Current Molecular Pharmacology Modulation of Toll-Like Receptor 4. Insights from X-Ray Crystallography and Molecular Modeling
Current Topics in Medicinal Chemistry CDK Inhibitors Induce Mitochondria-mediated Apoptosis Through the Activation of Polyamine Catabolic Pathway in LNCaP, DU145 and PC3 Prostate Cancer Cells
Current Pharmaceutical Design Versatile Synthesis of Organic Compounds Derived from Ascorbic Acid
Current Organocatalysis Is There a Role for Antioxidants in the Prevention of Infection-Associated Carcinogenesis and in the Treatment of Infection-Driven Tumors?
Current Topics in Medicinal Chemistry Isoform-Selective PI3K Inhibitors for Various Diseases
Current Topics in Medicinal Chemistry Influence of Dietary Substances on Intestinal Drug Metabolism and Transport
Current Drug Metabolism Multi- and Inter-Disciplinary Science in Personalized Delivery of Stem Cells for Tissue Repair
Current Stem Cell Research & Therapy MicroRNA-21: From Cancer to Cardiovascular Disease
Current Drug Targets WNT Signaling in Stem Cell Biology and Regenerative Medicine
Current Drug Targets Microdissection and the Study of Cancer Pathways
Current Molecular Medicine Characteristics of HSV-2, <i>M. genitalium</i> and <i>C. trachomatis</i> in HPV Genotypes Associated with Cervical Intraepithelial Neoplasia and Genital Infections
Infectious Disorders - Drug Targets Molecular Targeted Approaches to Cancer Therapy and Prevention Using Chalcones
Current Cancer Drug Targets miR-21, An Oncogenic Target miRNA for Cancer Therapy: Molecular Mechanisms and Recent Advancements in Chemo and Radio-resistance
Current Gene Therapy