Synthesis and biological evaluation of guanidine-type iminosugars

The Journal of Organic Chemistry
Matilde AguilarJ M García Fernández

Abstract

The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose --> piperidine rearrangement of 5-deoxy-5-guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

References

Mar 28, 2001·Science·J Alper
Mar 28, 2001·Science·P M RuddR A Dwek
Nov 10, 2001·The Journal of Organic Chemistry·M I García-MorenoJ M García Fernández
Mar 22, 2002·Journal of Virology·Shu-Fen WuYi-Ling Lin
Jul 19, 2002·Chemical Communications : Chem Comm·M Isabel García-MorenoJosé M García Fernández
Feb 7, 2003·Current Topics in Medicinal Chemistry·P GreimelT M Wrodnigg
Apr 30, 2003·Proceedings of the National Academy of Sciences of the United States of America·Davor PavlovićNicole Zitzmann
Jun 25, 2003·Glycoconjugate Journal·H Paulsen, I Brockhausen
Nov 8, 2003·The Journal of Organic Chemistry·M Isabel García-MorenoJosé M García Fernández
Nov 8, 2003·Journal of Inherited Metabolic Disease·T M CoxUNKNOWN Advisory Council to the European Working Group on Gaucher Disease
Dec 17, 2003·Proceedings of the National Academy of Sciences of the United States of America·Junichiro MatsudaYoshiyuki Suzuki
May 11, 2004·The Journal of Organic Chemistry·M Isabel García-MorenoJosé M García Fernández
May 12, 2004·Mini Reviews in Medicinal Chemistry·Tanja M Wrodnigg, Friedrich K Fitz Sprenger
Jul 1, 2006·The Journal of Organic Chemistry·José L Jiménez BlancoJosé M García Fernandez
Nov 14, 2006·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·J-Y SunJ-B Wang

❮ Previous
Next ❯

Citations

Jun 14, 2013·Glycoconjugate Journal·Amrita Srivastava, Duraikkannu Loganathan
Apr 5, 2011·Expert Opinion on Therapeutic Patents·Juan M BenitoCarmen Ortiz Mellet
Apr 5, 2016·Chemical Communications : Chem Comm·Elena M Sánchez-FernándezCarmen Ortiz Mellet
Oct 16, 2009·Chembiochem : a European Journal of Chemical Biology·Zhuo LuanYoshiyuki Suzuki
Apr 23, 2013·Chembiochem : a European Journal of Chemical Biology·Pilar AlfonsoPilar Giraldo
Mar 5, 2014·Organic & Biomolecular Chemistry·Julio Rodríguez-LavadoJosé M García Fernández
Apr 24, 2020·Chemical Communications : Chem Comm·Manuel González-CuestaJosé M García Fernández
Jun 18, 2009·Organic & Biomolecular Chemistry·Matilde Aguilar-MoncayoJosé M García Fernández
Apr 21, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Teresa Mena-BarragánCarmen Ortiz Mellet
Aug 11, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Elena M Sánchez-FernándezCarmen Ortiz Mellet
Jul 18, 2009·Organic Letters·Elena M Sánchez-FernándezJosé M García Fernández
Jun 30, 2010·The Journal of Organic Chemistry·Andrés G SantanaConcepción C González

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

© 2021 Meta ULC. All rights reserved