Heteroatom–heteroatom bond formation in natural product biosynthesis

AJ Waldman, TL Ng, P Wang, EP Balskus - Chemical Reviews, 2017 - ACS Publications
Natural products that contain functional groups with heteroatom-heteroatom linkages (X–X,
where X= N, O, S, and P) are a small yet intriguing group of metabolites. The reactivity and …

Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry

T Mendgen, C Steuer, CD Klein - Journal of medicinal chemistry, 2012 - ACS Publications
Rhodanines and related five-membered heterocycles with multiple heteroatoms have
recently gained a reputation of being unselective compounds that appear as “frequent …

The vinylogous aldol addition of heterocyclic silyloxy dienes: Application in synthesis

G Rassu, F Zanardi, L Battistini, G Casiraghi - Synlett, 1999 - thieme-connect.com
Open-chain dienolate motifs, deriving from deprotonation of a, b-unsaturated carbonyl
compounds, have been recently introduced as practically applicable building blocks for …

Heteroaromatic rings of the future

WR Pitt, DM Parry, BG Perry… - Journal of medicinal …, 2009 - ACS Publications
Small aromatic ring systems are of central importance in the development of novel synthetic
protein ligands. Here we generate a complete list of 24847 such ring systems. We call this …

Conformational restriction and/or steric hindrance in medicinal chemistry

A Mann - The practice of medicinal chemistry, 2008 - Elsevier
Publisher Summary The understanding of the thermodynamics of the events that are
governing molecular recognition is essential for the practice of medicinal chemistry. This …

A “traceless” Staudinger ligation for the chemoselective synthesis of amide bonds

E Saxon, JI Armstrong, CR Bertozzi - Organic letters, 2000 - ACS Publications
Here we report a novel modification of our previously reported “Staudinger ligation” that
generates an amide bond from an azide and a specifically functionalized phosphine. This …

1, 4-Diazaspiro [2.2] pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads

JW Rigoli, LA Boralsky, JC Hershberger… - The Journal of …, 2012 - ACS Publications
Nitrogen-containing stereotriads occur in a number of biologically active compounds, but
general and flexible methods to access these compounds are limited mainly to the …

Oxetanes in Drug Discovery Campaigns

JJ Rojas, JA Bull - Journal of Medicinal Chemistry, 2023 - ACS Publications
The oxetane ring is an emergent, underexplored motif in drug discovery that shows attractive
properties such as low molecular weight, high polarity, and marked three-dimensionality …

Expanding the Chemistry of Dihaloacetamides as Tunable Electrophiles for Reversible Covalent Targeting of Cysteines

D Yamane, R Tetsukawa, N Zenmyo… - Journal of Medicinal …, 2023 - ACS Publications
The choice of an appropriate electrophile is crucial in the design of targeted covalent
inhibitors (TCIs). In this report, we systematically investigated the glutathione (GSH) …

A new and versatile allylic alcohol anion and acyl β-anion equivalent for three-carbon homologations

R Caputo, A Guaragna, G Palumbo… - The Journal of Organic …, 1997 - ACS Publications
There are many reagents useful for the extension of organic molecules by three carbons
with some functionality at the new terminus. 1 However, to the best of our knowledge, the …