Targeted drugs by olefin metathesis: piperidine-based iminosugars

Drăguţan, Ileana; Drăguţan, Valerian; Demonceau, Albert

doi:10.1039/c1ra00910a

Cited by 96 publications

(37 citation statements)

References 127 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Finally, we investigated the synthesis of piperidyl dienes (entries 13-15) given the importance of nitrogen-containing heterocycles to the pharmaceutical industry. [26] Gratifyingly, the desired dienes could be synthesized in good yields [27] and high diastereoselectivities.…”

Section: Methodsmentioning

confidence: 99%

Single‐Electron/Pericyclic Cascade for the Synthesis of Dienes

Campbell

Sammis

2014

Angew Chem Int Ed

View full text Add to dashboard Cite

The highly efficient and diastereoselective synthesis of E dienes has been accomplished through radical cyclization of bromoallyl hydrazones. This methodology has been further extended to generate these products through a one-pot condensation/radical cyclization/cycloreversion cascade from simple aldehyde starting materials in high yields (>75%) and high diastereoselectivities (>95:5). Mechanistic investigations suggest that the cascade reaction proceeds through a cyclic diazene intermediate prior to the cycloreversion.

show abstract

Section: Methodsmentioning

confidence: 99%

Single‐Electron/Pericyclic Cascade for the Synthesis of Dienes

Campbell

Sammis

2014

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

“…1,2 The chemical and biological properties of these molecules can be greatly influenced by the location and configuration of carbon and heteroatom substituents. 2d Accordingly, numerous strategies have been developed to generate stereodefined, saturated, nitrogen heterocycles with various types of substitution.…”

mentioning

confidence: 99%

Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins

2014

View full text Add to dashboard Cite

A method for the enantioselective, intramolecular sulfenoamination of various olefins has been developed using a chiral BINAM-based selenophosphoramide, Lewis base catalyst. Terminal and trans disubstituted alkenes afforded pyrrolidines, piperidines, and azepanes in high yields and high enantiomeric ratios via enantioselective formation and subsequent stereospecific capture of the thiiranium intermediate with the pendant tosyl-protected amine.

show abstract

“…Although iminosugars have been extensively studied and have already found clinical use, recent efforts in their chemical synthesis coupled with an increased understanding of their affinity and target selectivity have notably improved their advancement as drug candidates. Efficient syntheses and new methods that allow to master the chemical and stereochemical complexity required are under continuous improvement …”

Section: Endocyclic Oxygen Replacementmentioning

confidence: 99%

Design and synthesis of glycomimetics: Recent advances

Tamburrini

Colombo

Bernardi

2019

Medicinal Research Reviews

View full text Add to dashboard Cite

In the past few decades, our understanding of glycan information‐encoding power has notably increased, thus leading to a significant growth also in the design and synthesis of glycomimetic probes. Combining data from multiple analytical sources, such as crystallography, nuclear magnetic resonance spectroscopy, and other biophysical methods (eg, surface plasmon resonance and carbohydrate microarrays) has allowed to shed light on the key interaction events between carbohydrates and their protein‐targets. However, the low metabolic stability of carbohydrates and their high hydrophilicity, which translates in low bioavailability, undermine their development as drugs. In this framework, the design of chemically modified analogues (called carbohydrate mimics or glycomimetics) appears as a valid alternative for the development of therapeutic agents. Glycomimetics, as structural and functional mimics of carbohydrates, can replace the native ligands in the interaction with target proteins, but are designed to show enhanced enzymatic stability and bioavailability and, possibly, an improved affinity and selectivity toward the target. In the present account, we specifically focus on the most recent advances in the design and synthesis of glycomimetics. In particular, we highlight the efforts of the scientific community in the development of straightforward synthetic procedures for the preparation of sugar mimics and in their preliminary biological evaluation.

show abstract

Targeted drugs by olefin metathesis: piperidine-based iminosugars

Cited by 96 publications

References 127 publications

Single‐Electron/Pericyclic Cascade for the Synthesis of Dienes

Single‐Electron/Pericyclic Cascade for the Synthesis of Dienes

Lewis Base Catalyzed, Enantioselective, Intramolecular Sulfenoamination of Olefins

Design and synthesis of glycomimetics: Recent advances

Contact Info

Product

Resources

About