The efficient synthesis of 2-aryl substituted pyrimidine acyclic nucleoside phosphonates using Liebeskind-Srogl cross-coupling

2011 ◽  
Author(s):  
Michal Česnek ◽  
Petra Břehová ◽  
Martin Dračínský ◽  
Antonín Holý ◽  
Zlatko Janeba
Keyword(s):  
Cross Coupling ◽  
Efficient Synthesis ◽  
Acyclic Nucleoside Phosphonates ◽  
Acyclic Nucleoside

The efficient synthesis of 2-arylpyrimidine acyclic nucleoside phosphonates using Liebeskind–Srogl cross-coupling reaction

Tetrahedron ◽  
2011 ◽  
Vol 67 (38) ◽  
pp. 7379-7385 ◽  
Author(s):  
Petra Břehová ◽  
Michal Česnek ◽  
Martin Dračínský ◽  
Antonín Holý ◽  
Zlatko Janeba
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Efficient Synthesis ◽  
Cross Coupling Reaction ◽  
Acyclic Nucleoside Phosphonates ◽  
Acyclic Nucleoside

Novel and Efficient Synthesis of gem -Difluorinated Derivatives of Acyclic Nucleoside Phosphonates (ANPs)

2016 ◽  
Vol 1 (10) ◽  
pp. 2102-2106 ◽  
Author(s):  
Karel Pomeisl ◽  
Petr Beier ◽  
Radek Pohl ◽  
Marcela Krečmerová
Keyword(s):  
Efficient Synthesis ◽  
Acyclic Nucleoside Phosphonates ◽  
Acyclic Nucleoside ◽  
Derivatives Of

Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines

2005 ◽  
Vol 70 (2) ◽  
pp. 247-258 ◽  
Author(s):  
Dana Hocková ◽  
Milena Masojídková ◽  
Antonín Holý
Keyword(s):  
Biological Activity ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Cross Coupling Reaction ◽  
Acyclic Nucleoside Phosphonates ◽  
Acyclic Nucleoside

Several 6-[(phosphonomethoxy)alkyl]pyrimidines and 6-[(phosphonomethoxy)alkynyl]pyrimidines were prepared as saturated and unsaturated carba-analogues of antivirally active 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidine. As the key step of their synthesis the Sonogashira cross-coupling reaction was successfully applied. The replacement of the C-O moiety by the C-C bond resulted in the loss of biological activity.

Efficient synthesis and biological properties of the 2′-trifluoromethyl analogues of acyclic nucleosides and acyclic nucleoside phosphonates

2011 ◽  
Vol 76 (10) ◽  
pp. 1187-1198 ◽  
Author(s):  
Petr Jansa ◽  
Viktor Kolman ◽  
Alexandra Kostinová ◽  
Martin Dračínský ◽  
Helena Mertlíková-Kaiserová ◽  
...  
Keyword(s):  
Biological Properties ◽  
Trifluoromethyl Group ◽  
Efficient Synthesis ◽  
Phosphonic Acids ◽  
Acyclic Nucleosides ◽  
Acyclic Nucleoside Phosphonates ◽  
Dialkyl Phosphonates ◽  
Acyclic Nucleoside ◽  
High Yields ◽  
Very High

Efficient and optimized procedure for the preparation of several acyclic nucleosides and acyclic nucleoside phosphonates substituted at the C-2′ position of the aliphatic part by the trifluoromethyl group is described. Trifluoromethyloxirane was found to be an excellent reagent for the introduction of the 1,1,1-trifluoropropan-2-ol moiety. Surprisingly, the next reaction of these 1,1,1-trifluoropropan-2-ols with the reagent for the introduction of the methylphosphonic residue afforded the desired phosphonates in very high yields and finally a novel simple and scalable procedure for the isolation of free phosphonic acids, after the reaction of dialkyl phosphonates with bromotrimethylsilane, was developed. Prepared compounds were evaluated for their biological properties, but none of the prepared phosphonic acids or acyclic nucleosides exhibits any antiviral, antiproliferative or anti-toxin activities.

scholarly journals Acyclic nucleoside phosphonates with a branched 2-(2-phosphonoethoxy)ethyl chain: Efficient synthesis and antiviral activity

2011 ◽  
Vol 19 (15) ◽  
pp. 4445-4453 ◽  
Author(s):  
Dana Hocková ◽  
Antonín Holý ◽  
Graciela Andrei ◽  
Robert Snoeck ◽  
Jan Balzarini
Keyword(s):  
Antiviral Activity ◽  
Efficient Synthesis ◽  
Acyclic Nucleoside Phosphonates ◽  
Acyclic Nucleoside

ChemInform Abstract: Efficient Synthesis and Biological Properties of the 2′-Trifluoromethyl Analogues of Acyclic Nucleosides and Acyclic Nucleoside Phosphonates.

ChemInform ◽  
2011 ◽  
Vol 43 (4) ◽  
pp. no-no
Author(s):  
Petr Jansa ◽  
Viktor Kolman ◽  
Alexandra Kostinova ◽  
Martin Dracinsky ◽  
Helena Mertlikova-Kaiserova ◽  
...  
Keyword(s):  
Biological Properties ◽  
Efficient Synthesis ◽  
Acyclic Nucleosides ◽  
Acyclic Nucleoside Phosphonates ◽  
Acyclic Nucleoside
Sign in / Sign up

Export Citation Format

Share Document