Evidence map›Paper›PMID 27827902›Full record

ReviewMarine drugs2016

Chiral Alkyl Halides: Underexplored Motifs in Medicine.

Bálint Gál, Cyril Bucher, Noah Z Burns

Abstract readReview
In one paragraph

Review in Marine drugs, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.

0numbers the graph read from it
0cells of the map it votes in
31citing 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

31 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Journal of the American Chemical Society · 2025
    Article
  6. Article
  7. Article
  8. Article
  9. Review
  10. Article
  11. Article
  12. Palladium-catalyzed remote internal C(spNature communications · 2024
    Article
  13. Article
  14. Regioselective C(spRSC advances · 2024
    Article
  15. Article
  16. Article
  17. Article
  18. Article
  19. Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023
    Review
  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

3 authors.

Bálint GálDepartment of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305, USA. bgal@stanford.edu.
Cyril BucherDepartment of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305, USA. cbucher@stanford.edu.
Noah Z BurnsDepartment of Chemistry, Stanford University, 333 Campus Drive, Stanford, CA 94305, USA. nburns@stanford.edu.

Funding

Selective Halogenation Reactions for the Synthesis of Chiral Bioactive Small MoleculesR01GM114061 · NIGMS · STANFORD UNIVERSITY · PI BURNS, NOAH ZACHARY · 2015 to 2019
$1.5M
NIGMS NIH HHS R01 GM114061
6 · The paper itself

Abstract

While alkyl halides are valuable intermediates in synthetic organic chemistry, their use as bioactive motifs in drug discovery and medicinal chemistry is rare in comparison. This is likely attributable to the common misconception that these compounds are merely non-specific alkylators in biological systems. A number of chlorinated compounds in the pharmaceutical and food industries, as well as a growing number of halogenated marine natural products showing unique bioactivity, illustrate the role that chiral alkyl halides can play in drug discovery. Through a series of case studies, we demonstrate in this review that these motifs can indeed be stable under physiological conditions, and that halogenation can enhance bioactivity through both steric and electronic effects. Our hope is that, by placing such compounds in the minds of the chemical community, they may gain more traction in drug discovery and inspire more synthetic chemists to develop methods for selective halogenation.

Indexed as

HalogenationAnimalsBiological ProductsHumansHydrocarbons, HalogenatedMolecular ConformationMolecular StructureStereoisomerismBiological ProductsHydrocarbons, Halogenatedalkyl halideanestheticastinsclindamycincorticosteroidforazolinehalomonlapachonelipophilicitypimecrolimusstereochemistrysucralose

Identifiers

PMID27827902
PMCPMC5128749

What OpenQuestion holds

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LicenceCC BY
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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.