The role of allylic strain for conformational control in medicinal chemistry

H Zhao, J Brånalt, M Perry… - Journal of Medicinal …, 2023 - ACS Publications
It is axiomatic in medicinal chemistry that optimization of the potency of a small molecule at a
macromolecular target requires complementarity between the ligand and target. In order to …

Triarylmethanes and their Medium‐Ring Analogues by Unactivated Truce–Smiles Rearrangement of Benzanilides

R Abrams, MH Jesani, A Browning… - Angewandte …, 2021 - Wiley Online Library
Intramolecular nucleophilic aromatic substitution (Truce–Smiles rearrangement) of the
anions of 2‐benzyl benzanilides leads to triarylmethanes in an operationally simple manner …

Theoretical Study on Acidities of (S)-Proline Amide Derivatives in DMSO and Its Implications for Organocatalysis

XY Huang, HJ Wang, J Shi - The Journal of Physical Chemistry A, 2010 - ACS Publications
The acidities (p K a values) of proline amide derivatives are of great importance for
understanding the catalytic activity of proline-based organocatalysts. The development of …

Reaction of carboxylic acids and isonitriles in small spaces

JL Hou, D Ajami, J Rebek Jr - Journal of the American Chemical …, 2008 - ACS Publications
Reversible encapsulation complexes are applied to the reaction of isonitriles with carboxylic
acids. Encapsulation facilitates these reactions by amplifying the concentration of reactants …

Why Do N-Alkylated Anilides Bend Over? The Factors Dictating the Divergent Conformational Preferences of 2° and 3° N-Aryl Amides

GJ Pros, AJ Bloomfield - The Journal of Physical Chemistry A, 2019 - ACS Publications
The conformational preferences of 28 sterically and electronically diverse N-aryl amides
were determined using density functional theory (DFT), using the B3LYP functional and 6 …

Adamantyl antiestrogens with novel side chains reveal a spectrum of activities in suppressing estrogen receptor mediated activities in breast cancer cells

J Min, VS Guillen, A Sharma, Y Zhao… - Journal of medicinal …, 2017 - ACS Publications
To search for new antiestrogens more effective in treating breast cancers, we explored
alternatives to the acrylic acid side chain used in many antiestrogens. To facilitate our …

A True Reverse Anomeric Effect Does Exist After All: A Hydrogen Bonding Stereocontrolling Effect in 2-Iminoaldoses

E Matamoros, EMS Pérez, ME Light… - The Journal of …, 2024 - ACS Publications
The reverse anomeric effect is usually associated with the equatorial preference of nitrogen
substituents at the anomeric center. Once postulated as another anomeric effect with …

Discovery of 2-pyridylureas as glucokinase activators

RJ Hinklin, TD Aicher, DA Anderson… - Journal of Medicinal …, 2014 - ACS Publications
Glucokinase (GK) is the rate-limiting step for insulin release from the pancreas in response
to high levels of glucose. Flux through GK also contributes to reducing hepatic glucose …

From Potential Prebiotic Synthons to Useful Chiral Scaffolds: A Synthetic and Structural Reinvestigation of 2-Amino-Aldononitriles

E Matamoros, ME Light, P Cintas, JC Palacios - Molecules, 2024 - mdpi.com
This paper explores and revisits in detail the formation and characterization of sugar-based
aminonitriles, whose ultimate origin can be traced to the interaction of biomolecules with …

Relative hydrophilicities of cis and trans formamides

YS Li, L Escobar, YJ Zhu, Y Cohen… - Proceedings of the …, 2019 - National Acad Sciences
Secondary formamides are widely encountered in biology and exist as mixtures of both cis
and trans isomers. Here, we assess hydrophilicity differences between isomeric formamides …