About: Novel Isoxazolidine and γ-Lactam Analogues of Homonucleosides

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About: Novel Isoxazolidine and γ-Lactam Analogues of Homonucleosides Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : wasabi.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
title	Novel Isoxazolidine and γ-Lactam Analogues of Homonucleosides
Creator	Schols, Dominique Andrei, Graciela Snoeck, Robert Gotkowska, Joanna Głowacka, Iwona Piotrowska, Dorota
source	Medline; PMC
abstract	Homonucleoside analogues cis-16 and trans-17 having a (5-methoxycarbonyl)isoxazolidine framework were synthesized via the 1,3-dipolar cycloaddition of nucleobase-derived nitrones with methyl acrylate. Hydrogenolysis of the isoxazolidines containing thymine, dihydrouracil, theophylline and adenine moieties efficiently led to the formation of the respective γ-lactam analogues. γ-Lactam analogues having 5-bromouracil and 5-chlorouracil fragments were synthesized by treatment of uracil-containing γ-lactams with NBS and NCS. Isoxazolidine and γ-lactam analogues of homonucleosides obtained herein were evaluated for activity against a broad range of DNA and RNA viruses. None of the compounds that were tested exhibited antiviral or cytotoxic activity at concentrations up to 100 µM. The cytostatic activities of all compounds toward nine cancerous cell lines was tested. γ-Lactams trans-15e (Cl-Ura) and cis-15h (Theo) appeared the most active toward pancreatic adenocarcinoma cells (Capan-1), showing IC(50) values 21.5 and 18.2 µM, respectively. Isoxazolidine cis-15e (Cl-Ura) inhibited the proliferation of colorectal carcinoma (HCT-116).
has issue date	2019-11-06(xsd:dateTime)
bibo:doi	10.3390/molecules24224014
bibo:pmid	31698778
has license	cc-by
sha1sum (hex)	8a2ca0a9b9108a56a79d6a610c6537102c124697
schema:url	https://doi.org/10.3390/molecules24224014
resource representing a document's title	Novel Isoxazolidine and γ-Lactam Analogues of Homonucleosides
has PubMed Central identifier	PMC6891762
has PubMed identifier	31698778
schema:publication	Molecules
resource representing a document's body	covid:8a2ca0a9b9108a56a79d6a610c6537102c124697#body_text
is schema:about of	named entity '5-BROMOURACIL' named entity 'TREATMENT' named entity 'LACTAMS' named entity 'INHIBITED' named entity 'DERIVED' named entity 'TRANS' named entity 'THYMINE' named entity 'FRAGMENTS' named entity 'SYNTHESIZED' named entity 'DIHYDROURACIL' named entity 'CONCENTRATIONS' named entity 'URA' named entity 'evaluated' named entity 'cis' named entity 'dihydrouracil' named entity 'ISOXAZOLIDINE' named entity 'NOVEL' covid:arg/8a2ca0a9b9108a56a79d6a610c6537102c124697 named entity 'TESTED' named entity 'NITRONES' named entity 'ACTIVITY' named entity 'THEOPHYLLINE' named entity 'CONTAINING' named entity 'METHYL ACRYLATE' named entity 'RANGE' named entity 'COLORECTAL CARCINOMA' named entity '5-CHLOROURACIL' named entity 'NBS' named entity 'DIPOLAR CYCLOADDITION' named entity 'PANCREATIC ADENOCARCINOMA' named entity 'METHOXYCARBONYL' named entity 'ACTIVE' named entity 'LACTAM' named entity 'MOLECULES' named entity 'LACTAM' named entity 'CYTOTOXIC' named entity 'CELL LINES' named entity 'ADENOCARCINOMA CELLS' named entity '15H' named entity '18.2' named entity 'URACIL' named entity 'ISOXAZOLIDINE' named entity 'CYTOSTATIC' named entity 'PROLIFERATION' named entity '116' named entity 'DNA' named entity 'NCS' named entity 'RNA VIRUSES' named entity 'BROAD' named entity 'OBTAINED' named entity 'CIS' named entity 'LED' named entity 'UP TO' named entity 'NUCLEOBASE' named entity '100' named entity 'ADENINE' named entity 'ANTIVIRAL' named entity 'FORMATION' named entity 'EVALUATED' named entity 'HYDROGENOLYSIS' named entity 'VALUES' named entity 'ACTIVITIES' named entity 'formation' named entity 'RNA' named entity 'range' named entity 'inhibited' named entity 'carcinoma' named entity 'NBS' named entity 'nitrones' named entity 'cytostatic' named entity 'adenine' named entity 'uracil' named entity 'cell lines' named entity 'colorectal carcinoma' named entity '1,3-dipolar cycloaddition' named entity 'theophylline'

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