ArticlePloS one2018
Rapid assessment of conformational preferences in biaryl and aryl carbonyl fragments.
Article in PloS one, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 35 citations in OpenAlex.
- Quantitative approaches to understanding conformational flexibility in crystalline sponges.CrystEngComm · 2026Article
- Biphenyl as a Privileged Structure in Medicinal Chemistry: Advances in Anti-Infective Drug Discovery.Molecules (Basel, Switzerland) · 2026Review
- FragPT2: Multifragment Wave Function Embedding with Perturbative Interactions.Journal of chemical theory and computation · 2025Article
- Synthetic studies on the tetrasubstituted D-ring of cystobactamids lead to potent terephthalic acid antibiotics.Communications chemistry · 2024Article
- Open Force Field BespokeFit: Automating Bespoke Torsion Parametrization at Scale.Journal of chemical information and modeling · 2022Article
- Leveraging Atropisomerism to Obtain a Selective Inhibitor of RET Kinase with Secondary Activities toward EGFR Mutants.ACS chemical biology · 2019Article
- Transoid-to-Cisoid Conformation Changes of Single Molecules on Surfaces Triggered by Metal Coordination.ACS omega · 2018Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The ability to rapidly assess the preferred conformation of key fragments in a structure "by visual inspection" is a very useful starting point in the process of drug design. With the ability to do so, one could address questions like: "How could we avoid planarity in a molecule?", "Will a molecule change its conformational preference if we make it more or less basic?" or "How does this electronic repulsion affect the conformational preference in the system?" in timely fashion. In this paper, we describe how the conformational energy profile (CEP, plot of energy as a function of dihedral bond angle) of a fragment can be interpreted through the understanding the interplay between resonance stabilization, steric effects and electrostatic interactions. Fifty-nine biaryl and aryl carbonyl fragments present in oral drugs or which are close derivatives thereof were selected. Calculation of their CEPs using ab initio methodology allowed us to conclude the relative importance of these factors in the conformational preference of these fragments as follows: "steric repulsion > lone pair-lone pair repulsion > lone pair-fluorine repulsion > resonance stabilization" and to formulate "rules of thumb" that the practicing medicinal/organic chemist can apply when analysing molecules that contain these fragments.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.