ArticleACS medicinal chemistry letters2022
Bioisostere Effects on the EPSA of Common Permeability-Limiting Groups.
Article in ACS medicinal chemistry letters, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
13 citing papers in PubMed.
- Structure-based design and synthesis of group A streptogramins that bind to the nascent peptide exit tunnel of the ribosome.European journal of medicinal chemistry · 2026Article
- Electrosynthesis of 1,1-Bis(difluoromethyl)alkenes via Twofold C-H Difluoromethylation as Bioisosteres of Elusive 1,1-Enediols.Nature communications · 2026Article
- Do Amino-Oxetanes Resemble Amides? A Matched Molecular Pairs Property and Structural Comparison.Journal of medicinal chemistry · 2026Article
- Rational design, synthesis of some quinolinone-Schiff bases/ pyridazino[4,5-c]quinolinones with potent anti-lung cancer and antituberculosis performance.Scientific reports · 2025Article
- Accessing sulfonamides via formal SONature chemistry · 2025Article
- An Electrosynthesis of 1,3,4-Oxadiazoles from N-Acyl Hydrazones.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Innovative On-Resin and in Solution Peptidomimetics Synthesis via Metal-Free Photocatalytic Approach.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- Sandmeyer Chlorosulfonylation of (Hetero)Aromatic Amines Using DABSO as an SOOrganic letters · 2024Article
- Structure and Biosynthesis of Hectoramide B, a Linear Depsipeptide from Marine CyanobacteriumACS chemical biology · 2024Article
- Design and Discovery of Novel NLRP3 Inhibitors and PET Imaging Radiotracers Based on a 1,2,3-Triazole-Bearing Scaffold.Journal of medicinal chemistry · 2024Article
- One-Pot Synthesis of Sulfonamides from Unactivated Acids and Amines via Aromatic Decarboxylative Halosulfonylation.Journal of the American Chemical Society · 2023Article
- Design, Synthesis, and Evaluation of Novel ΔJournal of medicinal chemistry · 2023Article
- Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Polar molecular surface area provides a valuable metric when optimizing properties as varied as membrane permeability and efflux susceptibility. The EPSA method to measure this quantity has had a substantial impact in medicinal chemistry, providing insight into the conformational and stereoelectronic features that govern the polarity of small molecules, targeted protein degraders, and macrocyclic peptides. Recognizing the value of bioisosteres in replacing permeation-limiting polar groups, we determined the effects of common amide, carboxylic acid, and phenol bioisosteres on EPSA, using matched molecular pairs within the Merck compound collection. Our findings reinforce EPSA's utility in optimizing permeability, highlight bioisosteres within each class that are particularly effective in lowering EPSA and others, which despite widespread use, offer little to no such benefit. Our method for matched-pair identification is generalizable across large compound collections and, thus, may constitute a flexible platform to study the effects of bioisosterism both in EPSA and other in vitro assays.
Identifiers
What OpenQuestion holds
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.