Evidence map›Paper›PMID 21526820›Full record

ArticleACS combinatorial science2011

Synthesis of a stereochemically diverse library of medium-sized lactams and sultams via S(N)Ar cycloetherification.

Baudouin Gerard, Jeremy R Duvall, Jason T Lowe, Tiffanie Murillo, Jingqiang Wei, Lakshmi B Akella, Lisa A Marcaurelle

Abstract read
In one paragraph

Article in ACS combinatorial science, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.

0numbers the graph read from it
0cells of the map it votes in
27citing 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

27 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Automated Solid Phase Assisted Synthesis of a Heparan Sulfate Disaccharide Library.Organic chemistry frontiers : an international journal of organic chemistry · 2022
    Article
  5. Article
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  7. Article
  8. Small-molecule enhancers of autophagy modulate cellular disease phenotypes suggested by human genetics.Proceedings of the National Academy of Sciences of the United States of America · 2015
    Article
  9. Review
  10. Discovery of a Small-Molecule Probe for V-ATPase Function.Journal of the American Chemical Society · 2015
    Article
  11. Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Article
  20. Article
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

7 authors.

Baudouin GerardChemical Biology Platform, The Broad Institute of Harvard and MIT, Cambridge Center, Massachusetts 02142, United States.
Jeremy R Duvall
Jason T Lowe
Tiffanie Murillo
Jingqiang Wei
Lakshmi B Akella
Lisa A Marcaurelle

Funding

The Incubator ProjectP50GM069721 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI SCHREIBER, STUART L · 2003 to 2012
$21.3M
Discovery Pipeline (2 of 4)RL1CA133834 · NCI · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI GOLUB, TODD R. · 2007 to 2011
$9.9M
Driving Medical Projects (4 of 4)RL1GM084437 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI SCOLNICK, EDWARD MARK · 2007 to 2011
$5.9M
Target ID (3 of 4)RL1HG004671 · NHGRI · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI SCHREIBER, STUART L · 2007 to 2011
$5.8M
Genomics Based Drug DiscoveryUL1RR024924 · NCRR · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI SCOLNICK, EDWARD MARK · 2007 to 2007
$352k
NCI NIH HHS RL1 CA133834NCI NIH HHS RL1CA133834NCRR NIH HHS UL1 RR024924NCRR NIH HHS UL1RR024924NHGRI NIH HHS RL1 HG004671NHGRI NIH HHS RL1HG004671NIGMS NIH HHS P50 GM069721NIGMS NIH HHS RL1 GM084437NIGMS NIH HHS RL1GM084437
6 · The paper itself

Abstract

We have implemented an aldol-based "build/couple/pair" (B/C/P) strategy for the synthesis of stereochemically diverse 8-membered lactam and sultam scaffolds via S(N)Ar cycloetherification. Each scaffold contains two handles, an amine and aryl bromide, for solid-phase diversification via N-capping and Pd-mediated cross coupling. A sparse matrix design strategy that achieves the dual objective of controlling physicochemical properties and selecting diverse library members was implemented. The production of two 8000-membered libraries is discussed including a full analysis of library purity and property distribution. Library diversity was evaluated in comparison to the Molecular Library Small Molecule Repository (MLSMR) through the use of a multifusion similarity (MFS) map and principal component analysis (PCA).

Indexed as

Combinatorial Chemistry TechniquesDrug DiscoveryLactamsMacrocyclic CompoundsModels, ChemicalSmall Molecule LibrariesStereoisomerismLactamsMacrocyclic CompoundsSmall Molecule Libraries

Identifiers

PMID21526820
PMCPMC3134123

What OpenQuestion holds

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Read underepoch 390

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.