Synthesis and Antiproliferative Evaluation of d-Glucuronamide-Based Nucleosides and (Triazolyl)methyl Amide-Linked Pseudodisaccharide Nucleosides.
N-glycosylation
antiproliferative activity
cycloaddition
d-glucuronamide
nucleoside analogs
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
14 Dec 2023
14 Dec 2023
Historique:
revised:
01
12
2023
received:
02
11
2023
medline:
14
12
2023
pubmed:
14
12
2023
entrez:
14
12
2023
Statut:
aheadofprint
Résumé
The synthesis and antiproliferative evaluation of novel d-glucopyranuronamide-containing nucleosides is described. Based on our previously reported anticancer d-glucuronamide-based nucleosides, new analogues comprising N/O-dodecyl or N-propargyl substituents at the glucuronamide unit and anomerically-N-linked 2-acetamido-6-chloropurine, 6-chloropurine or 4-(6-chloropurinyl)methyl triazole motifs were synthesized in 4-6 steps starting from acetonide-protected glucofuranurono-6,3-lactone. The methodologies were based on the access to N-substituted glycopyranuronamide precursors, namely 1,2-O-acetyl derivatives or glucuronoamidyl azides for further nucleobase N-glycosylation or 1,3-dipolar cycloaddition with N
Identifiants
pubmed: 38095428
doi: 10.1002/cmdc.202300608
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300608Subventions
Organisme : 'Fundacão para a Ciência e Tecnologia' (FCT)
ID : CEECIND/03881/2018
Organisme : 'Fundacão para a Ciência e Tecnologia' (FCT)
ID : EXPL/MED-QUI/1017/2021
Organisme : 'Fundacão para a Ciência e Tecnologia' (FCT)
ID : UIDB/00100/2020
Organisme : 'Fundacão para a Ciência e Tecnologia' (FCT)
ID : UIDP/00100/2020
Organisme : 'Fundacão para a Ciência e Tecnologia' (FCT)
ID : LA/P/0056/2020
Organisme : Instituto Nacional de Gestão de Bolsas de Estudos do Governo de Angola
Organisme : Instituto Superior de Ciências de Educação da Huíla
Informations de copyright
© 2023 Wiley-VCH GmbH.
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