About: Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides

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About: Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides 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	Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides
Creator	Bouton, Jakob Van Hecke, Kristof Calenbergh, Serge
source	Elsevier; Medline; PMC
abstract	Abstract Azanucleosides, sugar-modified nucleoside analogues containing a 4′ nitrogen atom, have shown a lot of therapeutic potential, e.g. as anti-cancer and antiviral agents. We report the synthesis of a series of 2’-homoazanucleosides, in which the nucleobase is attached to the 2’-position of the pyrrolidine ring via a methylene linker. A suitable orthogonally protected iminosugar was synthesized by ring closing metathesis and dihydroxylation as key steps and further converted to a series of 8 nucleoside analogues through Mitsunobu reaction with suitably protected nucleobases. The 5′ position of the adenine analogue was then further derivatized with thiols to afford 2 additional compounds. The final compounds were evaluated for biological activity.
has issue date	2017-07-27(xsd:dateTime)
bibo:doi	10.1016/j.tet.2017.05.083
bibo:pmid	32287431
has license	els-covid
sha1sum (hex)	9b59ae00fbafbb4fefc13e2cc6f3752472063300
schema:url	https://doi.org/10.1016/j.tet.2017.05.083
resource representing a document's title	Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides
has PubMed Central identifier	PMC7111761
has PubMed identifier	32287431
schema:publication	Tetrahedron
resource representing a document's body	covid:9b59ae00fbafbb4fefc13e2cc6f3752472063300#body_text
is schema:about of	named entity 'EFFICIENT' named entity 'ANALOGUE' named entity 'RING CLOSING METATHESIS' named entity 'NITROGEN ATOM' named entity 'NUCLEOBASES' named entity 'FINAL' named entity 'METHYLENE' named entity 'REPORT' named entity 'NUCLEOBASE' named entity 'THIOLS' named entity 'CLASS' named entity 'ANTIVIRAL AGENTS' named entity 'DIHYDROXYLATION' named entity 'NUCLEOSIDE ANALOGUES' named entity 'SYNTHESIS' named entity 'BIOLOGICAL ACTIVITY' named entity 'KEY' named entity 'CANCER' named entity 'EVALUATED' named entity 'PYRROLIDINE' named entity 'THERAPEUTIC' named entity 'HAVE' named entity 'ADENINE' named entity 'SYNTHESIS' named entity 'NEW' named entity 'ADDITIONAL' named entity 'MITSUNOBU REACTION' named entity 'MODIFIED' named entity 'LINKER' named entity 'POSITION' named entity 'ATTACHED TO' named entity 'RING' named entity 'SUGAR' named entity 'POTENTIAL' named entity 'CONTAINING' named entity 'SUITABLE' named entity 'A LOT OF' named entity 'STEPS' named entity 'SERIES' named entity 'mmol' named entity 'antiparasitic' named entity 'CH 2' named entity 'antibacterial activity' named entity 'Grubbs II' named entity 'NH 4' named entity 'methyl' named entity 'iminosugar' named entity 'thiols' named entity 'diastereoselective' named entity 'HCl' named entity 'nucleoside' named entity 'alkylation' named entity 'hexanes' named entity 'stereocenter' named entity 'number of bonds' named entity 'deprotection' named entity 'Vaccinia virus' named entity 'salts' named entity 'NaH' named entity 'mmol' named entity 'MeOH' named entity 'treatment of leukemia' named entity 'polarimeter' named entity 'mmol' named entity 'mmol' named entity 'TBAF' named entity 'Candida albicans' named entity 'Hexanes' named entity 'solubility' named entity 'reaction mixture' named entity 'nucleases' named entity 'mmol' named entity 'mesylate' named entity '1H NMR' named entity 'protecting groups' named entity 'salt' named entity 'Chemical shifts' named entity 'mmol' named entity '0.01'

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