Evidence map›Paper›PMID 29064688›Full record

ArticleJournal of the American Chemical Society2017

Enantioselective Total Synthesis of Antibiotic CJ-16,264, Synthesis and Biological Evaluation of Designed Analogues, and Discovery of Highly Potent and Simpler Antibacterial Agents.

K C Nicolaou, Kiran Kumar Pulukuri, Stephan Rigol, Marek Buchman, Akshay A Shah, Nicholas Cen, Megan D McCurry, Kathryn Beabout, Yousif Shamoo

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing 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

3 citing papers in PubMed.

  1. Article
  2. Article
  3. Scalable Access to Arylomycins via C-H Functionalization Logic.Journal of the American Chemical Society · 2018
    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

9 authors.

K C NicolaouDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.ORCID 0000-0001-5332-2511
Kiran Kumar PulukuriDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
Stephan RigolDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.ORCID 0000-0003-2470-3512
Marek BuchmanDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
Akshay A ShahDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.ORCID 0000-0001-9451-0869
Nicholas CenDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
Megan D McCurryDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.
Kathryn BeaboutDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.ORCID 0000-0003-2353-9685
Yousif ShamooDepartment of Chemistry, BioScience Research Collaborative and ‡Department of BioSciences, Rice University , 6100 Main Street, Houston, Texas 77005, United States.ORCID 0000-0001-9241-8962

Funding

TOTAL SYNTHESIS OF THIOSTREPTONR01AI055475 · NIAID · SCRIPPS RESEARCH INSTITUTE, THE · PI NICOLAOU, K. C. · 2002 to 2014
$7.0M
Defining Evolutionary Trajectories: Molecular adaptation to antibiotic resistanceR01AI080714 · NIAID · RICE UNIVERSITY · PI SHAMOO, YOUSIF · 2009 to 2023
$4.3M
NIAID NIH HHS R01 AI055475NIAID NIH HHS R01 AI080714
6 · The paper itself

Abstract

An improved and enantioselective total synthesis of antibiotic CJ-16,264 through a practical kinetic resolution and an iodolactonization reaction to form the iodo pyrrolizidinone fragment of the molecule is described. A series of racemic and enantiopure analogues of CJ-16,264 was designed and synthesized through the developed synthetic technologies and tested against drug-resistant bacterial strains. These studies led to interesting structure-activity relationships and the identification of a number of simpler, and yet equipotent, or even more potent, antibacterial agents than the natural product, thereby setting the foundation for further investigations in the quest for new anti-infective drugs.

Indexed as

Anti-Bacterial AgentsChemistry Techniques, SyntheticGram-Positive BacteriaGram-Positive Bacterial InfectionsHumansLactonesMicrobial Sensitivity TestsPyrazolesStereoisomerismStructure-Activity RelationshipAnti-Bacterial AgentsCJ-16,264LactonesPyrazoles

Identifiers

PMID29064688
PMCPMC5826612

What OpenQuestion holds

Textmetadata
LicenceTDM
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.