Abstract
The stereospecific synthesis of nine trans-combretastatin analogs (5 - 13) is described. The trans geometry of these products was ascertained by the vinylenic proton NMR coupling constants of 15 - 16 Hz, and also by a single crystal x-ray structure of the tetramethoxy compound 6. Continuous 3-day exposure of murine B16 melanoma cells to the trans-combretastatin analogs 5 - 13 showed that two of the analogs (2 and 4) had good cytotoxicity. According to a MTT assay, the IC50 values for compounds 2 and 4 were 4.5 μM and 13.5 μM, respectively. Compounds that exhibited cytotoxic properties contain a 4,4-dimethoxy-transstilbene skeleton.
Keywords: combretastatin, tubulin, anticancer, chugaev reaction, cytotoxicity
Letters in Drug Design & Discovery
Title: A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity
Volume: 1 Issue: 3
Author(s): Hari Pati, Zarmeen Taherbhai, Lori Forrest, Martha Wicks, Suzanna Bailey, Andrew Staples, Michelle Stewart, William Pennington, Jeffrey Harris and Moses Lee
Affiliation:
Keywords: combretastatin, tubulin, anticancer, chugaev reaction, cytotoxicity
Abstract: The stereospecific synthesis of nine trans-combretastatin analogs (5 - 13) is described. The trans geometry of these products was ascertained by the vinylenic proton NMR coupling constants of 15 - 16 Hz, and also by a single crystal x-ray structure of the tetramethoxy compound 6. Continuous 3-day exposure of murine B16 melanoma cells to the trans-combretastatin analogs 5 - 13 showed that two of the analogs (2 and 4) had good cytotoxicity. According to a MTT assay, the IC50 values for compounds 2 and 4 were 4.5 μM and 13.5 μM, respectively. Compounds that exhibited cytotoxic properties contain a 4,4-dimethoxy-transstilbene skeleton.
Export Options
About this article
Cite this article as:
Pati Hari, Taherbhai Zarmeen, Forrest Lori, Wicks Martha, Bailey Suzanna, Staples Andrew, Stewart Michelle, Pennington William, Harris Jeffrey and Lee Moses, A Stereospecific Route for the Preparation of Trans-Combretastatin Analogs: Synthesis and Cytotoxicity, Letters in Drug Design & Discovery 2004; 1 (3) . https://dx.doi.org/10.2174/1570180043398821
DOI https://dx.doi.org/10.2174/1570180043398821 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
- 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
-
Targeted Therapies in Hepatocellular Carcinoma
Current Medicinal Chemistry The Application of Natural Products in Cancer Therapy by Targeting Apoptosis Pathways
Current Drug Metabolism Formulation and Evaluation of Resveratrol Loaded Cubosomal Nanoformulation for Topical Delivery
Current Drug Delivery Overview of Prostate Biomarkers as Potential Targets for Immunotherapy
Current Cancer Therapy Reviews Diagnosis and Management of Lynch Syndrome
Recent Patents on Regenerative Medicine Is Metformin a Therapeutic Paradigm for Colorectal Cancer: Insight into the Molecular Pathway?
Current Drug Targets Advances in Development of Inhibitors of 17β-Hydroxysteroid Dehydrogenases
Anti-Cancer Agents in Medicinal Chemistry Effects of PPARγ Agonists against Vascular and Renal Dysfunction
Current Molecular Pharmacology Extracellular Matrix and Aberrant Signaling in Lung Carcinoma: Role of Fibronectin in the Control of Human Lung Carcinoma Cell Growth,Apoptosis and Resistance to Therapy
Current Signal Transduction Therapy Prediction by Pharmacogenetics of Safety and Efficacy of Non-Steroidal Anti- Inflammatory Drugs: A Review
Current Drug Metabolism The 21st Century Form of Vitamin E - Tocotrienol
Current Pharmaceutical Design Small Players With Big Roles: MicroRNAs as Targets to Inhibit Breast Cancer Progression
Current Drug Targets Angiogenesis Inhibitors: Implications for Combination with Conventional Therapies
Current Pharmaceutical Design Sentinel Node Imaging
Current Medical Imaging Transcriptional Regulation of mPGES1 in Cancer: An Alternative Approach to Drug Discovery?
Current Drug Targets Dipyridamole: A Drug with Unrecognized Antioxidant Activity
Current Topics in Medicinal Chemistry Targeting Tumor Lymphangiogenesis: An Update
Current Medicinal Chemistry Novel Hybrid Molecules of Quinazoline Chalcone Derivatives: Synthesis and Study of in vitro Cytotoxic Activities
Letters in Drug Design & Discovery Mechanisms of Cellular Resistance to Camptothecins
Current Medicinal Chemistry Ovarian Toxicity: From Environmental Exposure to Chemotherapy
Current Pharmaceutical Design