Abstract
Background: We report a novel MCR4 useful for generating chiral analogs of staurosporine a promiscuous and potent protein kinases inhibitor.
Method: Our strategy introduces the use of substituted tetramic acids as chiral precursors which together with an aldehyde, an isocyanide, a dienophile and a Lewis acid lead to hexa-substituted benzenes in one pot.
Conclusion: Interestingly, the use of chiral precursors not only allowed obtaining a stereo- controlled reaction, but also observing unusual atropo-diastereomers with axial chirality. The reaction can be carried out both under thermal or microwave conditions. The methodology is demonstrated for a panel of aldehydes, tetramic acids, isocyanides and dienophiles.
Keywords: Staurosporine, multicomponent reaction, Ugi, isocyanide, tetramic acid, hexa-substituted benzene, Meldrum's acid.
Current Organic Chemistry
Title:A New Multicomponent Reaction MCR4 for the Synthesis of Analogs of Staurosporine
Volume: 22 Issue: 5
Author(s): Mati Gelman, Tlalit Massarano, Ronit Lavi and Gerardo Byk*
Affiliation:
- Department of Chemistry, Exact Sciences Faculty, Bar Ilan University, Ramat Gan,Israel
Keywords: Staurosporine, multicomponent reaction, Ugi, isocyanide, tetramic acid, hexa-substituted benzene, Meldrum's acid.
Abstract: Background: We report a novel MCR4 useful for generating chiral analogs of staurosporine a promiscuous and potent protein kinases inhibitor.
Method: Our strategy introduces the use of substituted tetramic acids as chiral precursors which together with an aldehyde, an isocyanide, a dienophile and a Lewis acid lead to hexa-substituted benzenes in one pot.
Conclusion: Interestingly, the use of chiral precursors not only allowed obtaining a stereo- controlled reaction, but also observing unusual atropo-diastereomers with axial chirality. The reaction can be carried out both under thermal or microwave conditions. The methodology is demonstrated for a panel of aldehydes, tetramic acids, isocyanides and dienophiles.
Export Options
About this article
Cite this article as:
Gelman Mati , Massarano Tlalit , Lavi Ronit and Byk Gerardo *, A New Multicomponent Reaction MCR4 for the Synthesis of Analogs of Staurosporine, Current Organic Chemistry 2018; 22 (5) . https://dx.doi.org/10.2174/1385272821666170817110101
DOI https://dx.doi.org/10.2174/1385272821666170817110101 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Cutting-edge technology for the development of electrochemical sensors
Electrochemistry based point of care diagnostics is a powerful tool which can revolutionize the current concept of personalize health care industry. There have been several efforts to amalgamate cutting edge technologies (nanotechnology, surface technology, anti-biofouling strategies) while developing assays. The success of each electrochemical sensor is very dependable upon how ...read more
Electrochemical C-X bond formation
Conventional methods for carrying out carbon–X bond formation are typically conducted at harsh reaction conditions, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of ...read more
From Lab Bench to Algorithm: The Future of Organic Chemistry Powered by AI
Organic chemistry, with its intricate dance of molecules and reactions, is undergoing a transformation fuelled by the power of Artificial Intelligence (AI) and Machine Learning (ML). The integration of AI/ML with Organic Chemistry is revolutionizing the field by enhancing the efficiency and accuracy of chemical research and development. These technologies ...read more
Related Journals

- 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
- Announcements
Related Articles
-
Traumatic Brain Injury as a Risk Factor for Alzheimer’s Disease: Is Inflammatory Signaling a Key Player?
Current Alzheimer Research Natural Product Inhibitors of the Ubiquitin-Proteasome Pathway
Current Drug Targets Integrating In Vitro Kinetic Data from Compounds Exhibiting Induction, Reversible Inhibition and Mechanism-Based Inactivation: In Vitro Study Design
Current Drug Metabolism The Relationship Between Inflammation and the Anticoagulant Pathway: The Emerging Role of Endothelial Nitric Oxide Synthase (eNOS)
Current Pharmaceutical Design Microvascular Endothelial Dysfunction in Obesity and Hypertension
Current Pharmaceutical Design Influence of Gender on C-Reactive Protein, Fibrinogen, and Erythrocyte Sedimentation Rate in Obstructive Sleep Apnea
Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry Ziconotide: Neuronal Calcium Channel Blocker for Treating Severe Chronic Pain
Current Medicinal Chemistry Application of Proteomics in Cardiovascular Research
Current Proteomics B Lymphocyte Memory in X-Linked Lymphoproliferative Disease (XLP)
Current Immunology Reviews (Discontinued) Humanized SCID Mice Models of SLE
Current Pharmaceutical Design Inflammation in Chronic Obstructive Pulmonary Disease: Implications for New Treatment Strategies
Current Medicinal Chemistry Targeting Signaling Pathways in Chronic Lymphocytic Leukemia
Current Cancer Drug Targets Advances in the Development of Inactivated Virus Vaccines
Recent Patents on Anti-Infective Drug Discovery Nuciferine Inhibits Skin Cutaneous Melanoma Cell Growth by Suppressing TLR4/NF-κB Signaling
Anti-Cancer Agents in Medicinal Chemistry Oleanolic Acid Derived from Plants: Synthesis and Pharmacological Properties of A-ring Modified Derivatives
Letters in Drug Design & Discovery Pharmacological Screening of Lantana camara for its Antiallergic Activity in Rodents
Clinical Anti-Inflammatory & Anti-Allergy Drugs (Discontinued) Luminescent Quantum Dots: A Very Attractive and Promising Tool in Biomedicine
Current Medicinal Chemistry IN MEMORIAM
Endocrine, Metabolic & Immune Disorders - Drug Targets Skin Cancers in Elderly Patients
Anti-Cancer Agents in Medicinal Chemistry Pyrazoline and Analogs: Substrate-based Synthetic Strategies
Current Organic Synthesis