Fluorinated carbohydrates as chemical probes for molecular recognition studies. Current status and perspectives

B Linclau, A Ardá, NC Reichardt, M Sollogoub… - Chemical Society …, 2020 - pubs.rsc.org
This review provides an extensive summary of the effects of carbohydrate fluorination with
regard to changes in physical, chemical and biological properties with respect to regular …

Fluorinated cycloalkyl building blocks for drug discovery

OO Grygorenko, KP Melnykov, S Holovach… - …, 2022 - Wiley Online Library
The review covers various aspects of fluorinated cycloalkyl (C3− C7) building blocks for drug
discovery, including their synthesis, key physicochemical properties, and biological and …

Systematic investigation of lipophilicity modulation by aliphatic fluorination motifs

B Jeffries, Z Wang, HR Felstead… - Journal of Medicinal …, 2020 - ACS Publications
Optimization of compound lipophilicity is a key aspect of drug discovery. The aim of this work
was to compare the lipophilicity modulations induced by 16 distinct known and novel …

Enantioselective construction of tertiary fluoride stereocenters by organocatalytic fluorocyclization

Q Wang, M Lübcke, M Biosca… - Journal of the …, 2020 - ACS Publications
1, 1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo
oxidative fluorocyclization reactions with in situ generated chiral iodine (III)-catalysts. The …

Introducing affinity and selectivity into galectin-targeting nanoparticles with fluorinated glycan ligands

SJ Richards, T Keenan, JB Vendeville… - Chemical …, 2021 - pubs.rsc.org
Galectins are potential biomarkers and therapeutic targets. However, galectins display
broad affinity towards β-galactosides meaning glycan-based (nano) biosensors lack the …

Modulation of the H-bond basicity of functional groups by α-fluorine-containing functions and its implications for lipophilicity and bioisosterism

Y Zafrani, G Parvari, D Amir… - Journal of Medicinal …, 2021 - ACS Publications
Modulation of the H-bond basicity (p K HB) of various functional groups (FGs) by attaching
fluorine functions and its impact on lipophilicity and bioisosterism considerations are …

Placing CF2 in the Center: Major Physicochemical Changes Upon a Minor Structural Alteration in Gem‐Difunctional Compounds

S Saphier, S Katalan, G Yacov… - … A European Journal, 2023 - Wiley Online Library
Fluorine atoms play an important role in all branches of chemistry and accordingly, it is very
important to study their unique and varied effects systematically, in particular, the structure …

Access to Enantioenriched β‐Hydroxy gem‐Difluorinated Heterocyclic and Acyclic Derivatives through Rh(III)‐Catalyzed Asymmetric Transfer Hydrogenation

L Bacheley, R Ravindra, G Guillamot… - Advanced Synthesis …, 2024 - Wiley Online Library
We report a process to access a variety of enantioenriched α‐gem‐difluorinated alcohols. A
Rh (III)‐catalyzed asymmetric transfer hydrogenation method was developed in 85–98 …

Enzymatic glycosylation involving fluorinated carbohydrates

CE Council, KJ Kilpin, JS Gusthart, SA Allman… - Organic & …, 2020 - pubs.rsc.org
Fluorinated carbohydrates, where one (or more) fluorine atom (s) have been introduced into
a carbohydrate structure, typically through deoxyfluorination chemistry, have a wide range of …

Species-specific lipophilicities of fluorinated diketones in complex equilibria systems and their potential as multifaceted reversible covalent warheads

I Columbus, L Ghindes-Azaria, IM Herzog… - Communications …, 2023 - nature.com
Combined molecular, physicochemical and chemical properties of electrophilic warheads
can be applied to create covalent drugs with diverse facets. Here we study these properties …