Literature DB >> 11563079

Practical synthesis, separation, and stereochemical assignment of the PMPA pro-drug GS-7340.

H Chapman1, M Kernan, E Prisbe, J Rohloff, M Sparacino, T Terhorst, R Yu.   

Abstract

The practical synthesis of a mixed phenoxy-amidate derivative of PMPA with high oral bioavailability and favorable pharmacokinetics is described. The non-stereoselective synthetic route produces a 1:1 mixture of two diastereomers at phosphorous. Simulated moving bed chromatography using Chiralpak AS enabled kilo-scale isolation of the more potent diastereomer (GS-7340). The GS-7340 phosphorous chiral center was found to be (S) by X-ray crystallography.

Entities:  

Mesh:

Substances:

Year:  2001        PMID: 11563079     DOI: 10.1081/NCN-100002338

Source DB:  PubMed          Journal:  Nucleosides Nucleotides Nucleic Acids        ISSN: 1525-7770            Impact factor:   1.381


  15 in total

Review 1.  Synthesis of nucleoside phosphate and phosphonate prodrugs.

Authors:  Ugo Pradere; Ethel C Garnier-Amblard; Steven J Coats; Franck Amblard; Raymond F Schinazi
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

2.  Evaluation of nucleoside phosphonates and their analogs and prodrugs for inhibition of orthopoxvirus replication.

Authors:  Kathy A Keith; Michael J M Hitchcock; William A Lee; Antonin Holý; Earl R Kern
Journal:  Antimicrob Agents Chemother       Date:  2003-07       Impact factor: 5.191

Review 3.  Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases.

Authors:  Lars Petter Jordheim; David Durantel; Fabien Zoulim; Charles Dumontet
Journal:  Nat Rev Drug Discov       Date:  2013-06       Impact factor: 84.694

4.  Differential binding of tenofovir and adefovir to reverse transcriptase of hepatitis B virus.

Authors:  Formijn J van Hemert; Ben Berkhout; Hans L Zaaijer
Journal:  PLoS One       Date:  2014-09-02       Impact factor: 3.240

5.  ProTides of BVdU as potential anticancer agents upon efficient intracellular delivery of their activated metabolites.

Authors:  Sahar Kandil; Jan Balzarini; Stephanie Rat; Andrea Brancale; Andrew D Westwell; Christopher McGuigan
Journal:  Bioorg Med Chem Lett       Date:  2016-10-27       Impact factor: 2.823

Review 6.  Phosphoramidates and phosphonamidates (ProTides) with antiviral activity.

Authors:  Magdalena Slusarczyk; Michaela Serpi; Fabrizio Pertusati
Journal:  Antivir Chem Chemother       Date:  2018 Jan-Dec

Review 7.  The ProTide Prodrug Technology: From the Concept to the Clinic.

Authors:  Youcef Mehellou; Hardeep S Rattan; Jan Balzarini
Journal:  J Med Chem       Date:  2017-08-24       Impact factor: 7.446

Review 8.  Adenine: an important drug scaffold for the design of antiviral agents.

Authors:  Changyuan Wang; Zhendong Song; Haiqing Yu; Kexin Liu; Xiaodong Ma
Journal:  Acta Pharm Sin B       Date:  2015-09-02       Impact factor: 11.413

9.  Synthesis and Evaluation of Biological Activity of New Arylphosphoramidates.

Authors:  Amal Thebti; M A K Sanhoury; H-I Ouzari; T Barhoumi-Slimi
Journal:  Biomed Res Int       Date:  2018-08-26       Impact factor: 3.411

10.  Co-crystals, Salts or Mixtures of Both? The Case of Tenofovir Alafenamide Fumarates.

Authors:  Hannes Lengauer; Damjan Makuc; Damjan Šterk; Franc Perdih; Arthur Pichler; Tina Trdan Lušin; Janez Plavec; Zdenko Časar
Journal:  Pharmaceutics       Date:  2020-04-10       Impact factor: 6.321

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.