Evidence map›Paper›PMID 32301265›Full record

ArticleAngewandte Chemie (International ed. in English)2020

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs.

Christopher J Smedley, Gencheng Li, Andrew S Barrow, Timothy L Gialelis, Marie-Claire Giel, Alessandra Ottonello, Yunfei Cheng, Seiya Kitamura, Dennis W Wolan, K Barry Sharpless and 1 more

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 39 papers.

0numbers the graph read from it
0cells of the map it votes in
39citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

39 citing papers in PubMed.

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  12. Diversity Oriented Clicking for Modular Synthesis.Nature reviews. Methods primers · 2025
    Article
  13. SONature communications · 2024
    Article
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4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

11 authors.

Christopher J SmedleyLa Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC, 3086, Australia.ORCID 0000-0001-5110-2574
Gencheng LiDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA, 92037, USA.
Andrew S BarrowLa Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC, 3086, Australia.
Timothy L GialelisLa Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC, 3086, Australia.
Marie-Claire GielLa Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC, 3086, Australia.
Alessandra OttonelloLa Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC, 3086, Australia.
Yunfei ChengDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA, 92037, USA.
Seiya KitamuraDepartment of Molecular Medicine, The Scripps Research Institute, La Jolla, CA, 92037, USA.
Dennis W WolanDepartment of Molecular Medicine, The Scripps Research Institute, La Jolla, CA, 92037, USA.
K Barry SharplessDepartment of Chemistry, The Scripps Research Institute, La Jolla, CA, 92037, USA.ORCID 0000-0001-6051-1599
John E MosesLa Trobe Institute for Molecular Science, La Trobe University, Melbourne, VIC, 3086, Australia.ORCID 0000-0003-2162-3234

Funding

Single-Cell Biology Shared ResourceP30CA045508 · NCI · COLD SPRING HARBOR LABORATORY · PI John Edward Moses · 1987 to 2026
$118.9M
Project 9P50GM103368 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI ARNOLD, EDWARD · 2012 to 2016
$20.0M
X-ray Crystallographic Fragment Screening CoreU54AI150472 · NIAID · SEATTLE CHILDREN'S HOSPITAL · PI LYUMKIS, DMITRY · 2019 to 2021
$15.7M
Sulfur(VI) Fluoride Exchange (SuFEx): new developments and biological applicationsR01GM117145 · NIGMS · SCRIPPS RESEARCH INSTITUTE, THE · PI SHARPLESS, KARL BARRY · 2016 to 2023
$3.9M
NCI NIH HHS P30 CA045508NIAID NIH HHS U54 AI150472NIGMS NIH HHS P50 GM103368NIGMS NIH HHS R01 GM117145
6 · The paper itself

Abstract

Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving "diversity with ease", by combining classic C-C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels-Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates-demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.

Indexed as

Click ChemistryCycloaddition ReactionMolecular StructureSulfinic AcidsSulfinic Acidssulfuryl fluoridecycloadditionsdiversity oriented clickingheterocyclesSuFEx click chemistrysulfonyl fluorides

Identifiers

PMID32301265
PMCPMC7572632

What OpenQuestion holds

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Registered trials

None linked

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.