Evidence map›Paper›PMID 39518987›Full record

ArticleInternational journal of molecular sciences2024

1,3-Dipolar Cycloaddition of Nitrile Oxides and Nitrilimines to (-)-β-Caryophyllene: Stereoselective Synthesis of Polycyclic Derivatives and Their Biological Testing.

Dmitry E Shybanov, Maxim E Kukushkin, Yuri K Grishin, Vitaly A Roznyatovsky, Viktor A Tafeenko, Louay Abo Qoura, Vadim S Pokrovsky, Olga I Yarovaya, Svetlana V Belyaevskaya, Alexandrina S Volobueva and 3 more

Abstract read
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In one paragraph

Article in International journal of molecular sciences, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing 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

1 citing paper in PubMed.

  1. 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

13 authors.

Dmitry E ShybanovDepartment of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
Maxim E KukushkinDepartment of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
Yuri K GrishinDepartment of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.ORCID 0000-0001-7709-5245
Vitaly A RoznyatovskyDepartment of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.ORCID 0000-0002-5673-8931
Viktor A TafeenkoDepartment of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.
Louay Abo QouraResearch Institute of Molecular and Cellular Medicine, People's Friendship University of Russia (RUDN University), 117198 Moscow, Russia.ORCID 0000-0001-5391-5077
Vadim S PokrovskyResearch Institute of Molecular and Cellular Medicine, People's Friendship University of Russia (RUDN University), 117198 Moscow, Russia.
Olga I YarovayaN.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, 630090 Novosibirsk, Russia.ORCID 0000-0002-2333-4893
Svetlana V BelyaevskayaPasteur Research Institute of Epidemiology and Microbiology, 14 MiraStr, 197101 St. Petersburg, Russia.
Alexandrina S VolobuevaPasteur Research Institute of Epidemiology and Microbiology, 14 MiraStr, 197101 St. Petersburg, Russia.
Iana L EsaulkovaPasteur Research Institute of Epidemiology and Microbiology, 14 MiraStr, 197101 St. Petersburg, Russia.
Vladimir V ZarubaevPasteur Research Institute of Epidemiology and Microbiology, 14 MiraStr, 197101 St. Petersburg, Russia.ORCID 0000-0002-5224-3771
Elena K BeloglazkinaDepartment of Chemistry, M. V. Lomonosov Moscow State University, 119991 Moscow, Russia.

Funding

Russian Science Foundation 24-13-00004
6 · The paper itself

Abstract

The cycloaddition of nitrile oxides and nitrilimines to one or both of the C=C double bonds of caryophyllene is described. The possibility of introducing five-membered fused and spiro-linked heterocycles into the structure of sesquiterpenes by the 1,3-dipolar cycloaddition reactions of nitrile oxides and nitrilimines to caryophyllene was demonstrated. As a result of these reactions, pharmacophore fragments of isoxazoline and pyrazoline are introduced into the structure of caryophyllene, which leads to an increase in the conformational rigidity of the molecule. A complete stereochemical assignment of 1,3-dipolar cycloaddition adducts to caryophyllene was carried out. The study of antiviral and cytotoxic activity for some heterocyclic derivatives synthesized in this work revealed relatively high biological activity of previously little-studied cycloaddition adducts at the exocyclic C=CH

Indexed as

Antiviral AgentsCycloaddition ReactionNitrilesPolycyclic SesquiterpenesAnimalsDogsHumansIminesInfluenza A Virus, H1N1 SubtypeMadin Darby Canine Kidney CellsOxidesSesquiterpenesStereoisomerismAntiviral AgentscaryophylleneIminesNitrilesOxidesPolycyclic SesquiterpenesSesquiterpenes1,3-dipolar cycloadditionantiviral activitycaryophyllenecytotoxicitynitrile oxidesnitrilimines

Identifiers

PMID39518987
PMCPMC11545984

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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.