About: Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations

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About: Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations Goto Sponge NotDistinct Permalink

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

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type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
title	Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations
Creator	Schols, Dominique Andrei, Graciela Snoeck, Robert Makuc, Damjan Mintas, Mladen Plavec, Janez Wittine, Karlo Kraljevi C Paveli C D , Kre Simir Paveli C D, Sandra Martinovi, Tamara Stipkovi C Babi C A, Maja
source	Elsevier; Medline; PMC
abstract	Abstract Keeping the potential synergy of biological activity of synthetic anomalous derivatives of deazapurines and l-ascorbic acid (l-AA) in mind, we have synthesized new 3-, 7- and 9-deazapurine derivatives of l-ascorbic (1–4, 8–10, 13–15) and imino-l-ascorbic acid (5–7, 11, 12, 16–19). These novel compounds were evaluated for their cytostatic and antiviral activity in vitro against a panel of human malignant tumour cell lines and normal murine fibroblasts (3T3). Among all evaluated compounds, the 9-deazapurine derivative of l-AA (13) exerted the most potent inhibitory activity on the growth of CEM/0 cells (IC50 = 4.1 ± 1.8 μM) and strong antiproliferative effect against L1210/0 (IC50 = 4.7 ± 0.1 μM) while the 9-deazahypoxanthine derivative of l-AA (15) showed the best effect against HeLa cells (IC50 = 5.6 ± 1.3 μM) and prominent effect on L1210/0 (IC50 = 4.5 ± 0.5 μM). Furthermore, the 9-deazapurine derivative disubstituted with two imino-l-AA moieties (18) showed the best activity against L1210/0 tumour cells (IC50 = 4.4 ± 0.3 μM) and the most pronounced antiproliferative effects against MiaPaCa-2 cells (IC50 = 5.7 ± 0.2 μM). All these compounds showed selective cytostatic effect on tumour cell lines in comparison with embryonal murine fibroblasts (3T3). When evaluating their antiviral activity, the 3-deazapurine derivative of l-AA (3) exhibited the highest activity against both laboratory-adapted strains of human cytomegalovirus (HCMV) (AD-169 and Davis) with EC50 values comparable to those of the well-known anti-HCMV drug ganciclovir and without cytotoxic effects on normal human embryonal lung (HEL) cells.
has issue date	2015-09-18(xsd:dateTime)
bibo:doi	10.1016/j.ejmech.2015.08.008
bibo:pmid	26291038
has license	els-covid
sha1sum (hex)	507e89af048133bdd35f4f40903bbaa0a4ed0b6f
schema:url	https://doi.org/10.1016/j.ejmech.2015.08.008
resource representing a document's title	Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations
has PubMed Central identifier	PMC7125971
has PubMed identifier	26291038
schema:publication	European Journal of Medicinal Chemistry
resource representing a document's body	covid:507e89af048133bdd35f4f40903bbaa0a4ed0b6f#body_text
is schema:about of	named entity 'cytostatic' named entity 'activity' named entity 'embryonal' named entity 'synthesized' named entity 'All' named entity 'normal' covid:arg/507e89af048133bdd35f4f40903bbaa0a4ed0b6f named entity 'fibroblasts' named entity 'derivative' named entity 'cells' named entity 'biological activity' named entity 'activity' named entity 'HCMV' named entity 'potent' named entity 'human' named entity 'moieties' named entity 'cell lines' named entity 'evaluated' named entity 'ganciclovir' named entity 'Novel' named entity 'lung' named entity 'fibroblasts' named entity 'HeLa cells' named entity 'imino' named entity 'embryonal' named entity 'HCMV' named entity 'cytotoxic effects' named entity 'embryonal' named entity 'antiviral activity' named entity 'halogenated' named entity '1,4-Dioxane' named entity 'embryonal' named entity '3T3' named entity 'adenosine kinase' named entity 'Mitsunobu reaction' named entity 'regioisomer' named entity 'dichloromethane' named entity 'Antiviral activity' named entity 'HMBC' named entity 'methanol' named entity 'L-ascorbic acid' named entity 'HCMV' named entity 'lung' named entity 'antitumour' named entity 'HBV' named entity 'dichloromethane' named entity '1, 2' named entity 'Methanol' named entity 'virus' named entity 'hexamethyldisilazane' named entity 'argon' named entity 'column chromatography' named entity 'PPh' named entity 'imino' named entity 'cell line' named entity 'L-ascorbic acid' named entity '2D NMR' named entity 'cytotoxic effects' named entity 'nucleoside' named entity 'boron' named entity 'dichloromethane' named entity 'coupling constant' named entity 'mouse embryonic fibroblast' named entity 'cell line' named entity 'column chromatography' named entity 'methanol' named entity 'benzyl' named entity 'Sigma Aldrich' named entity 'alkylated' named entity 'imino' named entity 'HepG2' named entity 'imino'

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