Prodrugs of Ara-CMP and Ara-AMP with aS-Acyl-2-thioethyl (SATE) Biolabile Phosphate Protecting Group: Synthesis and Biological Evaluation

Rita Bazzanini; Stefano Manfredini; Elisa Durini; Bettina Gröschel; J Cinátl; Jan Balzarini; De Clercq Erik; J‐L. Imbach; Christian Périgaud; Gilles Gosselin

doi:10.1080/15257779908041616

Back

Prodrugs of Ara-CMP and Ara-AMP with aS-Acyl-2-thioethyl (SATE) Biolabile Phosphate Protecting Group: Synthesis and Biological Evaluation

Article 1999 en

Abstract

1 min read

The bis(S-pivaloyl-2-thioethyl) phosphotriesters of Ara-C and Ara-A were synthesized as potential bioreversible mononucleotide prodrugs. Some N- and O-acylated derivatives were also prepared with the aim to modify the lipophilicity of the title pronucleotides. Compounds were tested for their antitumor/antiviral activity against a variety of tumor cells and viruses.

Related publications

Article1999

cycloSal-Pronucleotides of 2‘-Fluoro-ara- and 2‘-Fluoro-ribo-2‘,3‘- dideoxyadenosine as a Strategy to Bypass a Metabolic Blockade

Chris Meier, Tina Knispel, Víctor E. Márquez, M. Arshad Siddiqui, De Clercq Erik, Jan Balzarini

Article1999

cycloSal-Pronucleotides of 2‘,3‘-Dideoxyadenosine and 2‘,3‘-Dideoxy-2‘,3‘-didehydroadenosine: Synthesis and Antiviral Evaluation of a Highly Efficient Nucleotide Delivery System

Chris Meier, Tina Knispel, De Clercq Erik, Jan Balzarini

Article1995

5′,5′‐di‐O‐nucleosyl‐O′‐benzylphosphotriesters as potential prodrugs of 3′‐azido‐2′,3′‐dideoxythymidine‐5′‐monophosphate

Chris Meier, Lothar W. Habel, Jan Balzarini, De Clercq Erik

Article1997

Retinoic Acid Conjugates as Potential Antitumor Agents: Synthesis and Biological Activity of Conjugates with Ara-A, Ara-C, 3(2H)-Furanone, and Aniline Mustard Moieties

Stefano Manfredini, Daniele Simoni, Roberto Ferroni, Rita Bazzanini, Silvia Vertuani, Sigrid Hatse, Jan Balzarini, De Clercq Erik

Article2010

Synthesis of Ester Prodrugs of 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) as Anti-Poxvirus Agents

Marcela Krečmerová, Antonı́n Holý, Graciela Andreï, Karel Pomeisl, Tomáš Tichý, Petra Břehová, Milena Masojı́dková, Martin Dračínský, Radek Pohl, Geneviève Laflamme, Lieve Naesens, Hon C. Hui, Tomáš Cihlář, Johan Neyts, De Clercq Erik, Jan Balzarini, Robert Snoeck

Prodrugs of Ara-CMP and Ara-AMP with a<i>S</i>-Acyl-2-thioethyl (SATE) Biolabile Phosphate Protecting Group: Synthesis and Biological Evaluation

Abstract

Discussion(0)

Related publications

<i>cyclo</i>Sal-Pronucleotides of 2‘-Fluoro-<i>ara</i>- and 2‘-Fluoro-<i>ribo</i>-2‘,3‘- dideoxyadenosine as a Strategy to Bypass a Metabolic Blockade

<i>cyclo</i>Sal-Pronucleotides of 2‘,3‘-Dideoxyadenosine and 2‘,3‘-Dideoxy-2‘,3‘-didehydroadenosine: Synthesis and Antiviral Evaluation of a Highly Efficient Nucleotide Delivery System

5′,5′‐di‐<i>O</i>‐nucleosyl‐<i>O</i>′‐benzylphosphotriesters as potential prodrugs of 3′‐azido‐2′,3′‐dideoxythymidine‐5′‐monophosphate

Retinoic Acid Conjugates as Potential Antitumor Agents: Synthesis and Biological Activity of Conjugates with Ara-A, Ara-C, 3(2<i>H</i>)-Furanone, and Aniline Mustard Moieties

Synthesis of Ester Prodrugs of 9-(<i>S</i>)-[3-Hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) as Anti-Poxvirus Agents