A series of 2',3'-didehydro-2',3'-dideoxynucleosides substituted with an alkynylhydroxy- (6, 7, 12 and 13) and alkynylamino- (20) groups at the C-5 position were synthesized. All these five target modified nucleosides were tested for anti-human immunodeficiency virus type 1 activity in CEM-SS and MT-4 cells and unfortunately displayed no improvement in antiviral activity.
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http://dx.doi.org/10.1080/14756360412331280527 | DOI Listing |
J Org Chem
January 2021
School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, Trinity College Dublin, The University of Dublin, Dublin 2, 152-160 Pearse Street, Dublin, Ireland.
The bicyclo[1.1.1]pentane (BCP) unit is under scrutiny as a bioisostere in drug molecules.
View Article and Find Full Text PDFChem Commun (Camb)
August 2018
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, Uttar Pradesh, India.
3-Spiropiperidino indolenines have been synthesized via novel Lewis acid-catalyzed S2-type ring opening of activated aziridines with 1H-indoles followed by Pd-catalyzed dearomative spirocyclization with propargyl carbonates in up to 88% yields. The step and pot-economic transformation comprises sequential C-C, C-N, and C-C bond forming steps generating two stereogenic centers including an all-carbon quaternary stereocenter to furnish the products in diastereomerically pure (dr >99 : 1) forms with excellent enantiomeric excess (ee up to >99%). The synthetic versatility of the strategy has been illustrated by converting the synthesized products into spirocyclic indolenine 2-piperidinones, dihydropiperidines, and 5-alkynylated piperidines.
View Article and Find Full Text PDFNucleic Acids Symp Ser (Oxf)
November 2010
Institute of Bioorganic Chemistry, Polish Academy of Sciences, PL-61704 Poznan, Poland.
The synthesis of 5-ethynyl-1H-[1,2,3]triazole-4-carboxylic acid amide riboside 1 and its derivatives exploits Pd(0)-catalyzed cross-coupling reactions. The iodinated key intermediate 3a, when coupled with alkynes affords 5-alkynylated products 1b,c,e,f in diverse yields. Methanolysis of 1b and 1c provides the title compound 1 and the 5-propynyl derivative 1d, respectively.
View Article and Find Full Text PDFJ Enzyme Inhib Med Chem
December 2004
Centre d'Etudes et de Recherche sur le Médicament de Normandie, UFR des Sciences Pharmaceutiques, F-14032 Caen Cedex, France.
A series of 2',3'-didehydro-2',3'-dideoxynucleosides substituted with an alkynylhydroxy- (6, 7, 12 and 13) and alkynylamino- (20) groups at the C-5 position were synthesized. All these five target modified nucleosides were tested for anti-human immunodeficiency virus type 1 activity in CEM-SS and MT-4 cells and unfortunately displayed no improvement in antiviral activity.
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