Evidence map›Paper›PMID 35328816›Full record

ReviewInternational journal of molecular sciences2022

Improvements, Variations and Biomedical Applications of the Michaelis-Arbuzov Reaction.

Stavroula Kostoudi, Georgios Pampalakis

Abstract readReview
In one paragraph

Review in International journal of molecular sciences, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing 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

2 citing papers in PubMed.

  1. Iron-Photocatalyzed C(spAngewandte Chemie (International ed. in English) · 2026
    Article
  2. 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

2 authors.

Stavroula KostoudiDepartment of Pharmacognosy-Pharmacology, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
Georgios PampalakisDepartment of Pharmacognosy-Pharmacology, School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.ORCID 0000-0002-2119-4292

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Compounds bearing the phosphorus-carbon (P-C) bond have important pharmacological, biochemical, and toxicological properties. Historically, the most notable reaction for the formation of the P-C bond is the Michaelis-Arbuzov reaction, first described in 1898. The classical Michaelis-Arbuzov reaction entails a reaction between an alkyl halide and a trialkyl phosphite to yield a dialkylalkylphosphonate. Nonetheless, deviations from the classical mechanisms and new modifications have appeared that allowed the expansion of the library of reactants and consequently the chemical space of the yielded products. These involve the use of Lewis acid catalysts, green methods, ultrasound, microwave, photochemically-assisted reactions, aryne-based reactions, etc. Here, a detailed presentation of the Michaelis-Arbuzov reaction and its developments and applications in the synthesis of biomedically important agents is provided. Certain examples of such applications include the development of alkylphosphonofluoridates as serine hydrolase inhibitors and activity-based probes, and the P-C containing antiviral and anticancer agents.

Indexed as

Lewis AcidsPhosphorusAntiviral AgentsCatalysisMicrowavesAntiviral AgentsLewis AcidsPhosphorusactivity-based probesMichaelis–Arbuzov reactionpharmaceutical applicationsphosphonatesphosphonofluoridates

Identifiers

PMID35328816
PMCPMC8955222

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Registered trials

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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.