Literature DB >> 16134952

Cytostatic 6-arylpurine nucleosides. 6. SAR in anti-HCV and cytostatic activity of extended series of 6-hetarylpurine ribonucleosides.

Michal Hocek1, Petr Naus, Radek Pohl, Ivan Votruba, Phillip A Furman, Phillip M Tharnish, Michael J Otto.   

Abstract

Significant anti-HCV activity of 6-hetarylpurine ribonucleosides has been discovered and is reported here for the first time and compared with cytostatic effect. An extended series of 6-hetarylpurine nucleosides has been prepared by heterocyclizations in position 6 of purine nucleosides or by cross-couplings of 6-chloropurine nucleosides with hetarylboronic acids, -stannanes, or -zinc halides. The most anti-HCV active were purine ribonucleosides bearing pyrrol-3-yl or 2-furyl groups exerting EC(90) = 0.14 and 0.4 microM, respectively.

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Year:  2005        PMID： 16134952     DOI： 10.1021/jm050335x

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  8 in total

1.  Discovery of PSI-353661, a Novel Purine Nucleotide Prodrug for the Treatment of HCV Infection.

Authors:  Wonsuk Chang; Donghui Bao; Byoung-Kwon Chun; Devan Naduthambi; Dhanapalan Nagarathnam; Suguna Rachakonda; P Ganapati Reddy; Bruce S Ross; Hai-Ren Zhang; Shalini Bansal; Christine L Espiritu; Meg Keilman; Angela M Lam; Congrong Niu; Holly Micolochick Steuer; Phillip A Furman; Michael J Otto; Michael J Sofia
Journal:  ACS Med Chem Lett       Date:  2010-12-17       Impact factor: 4.345

2.  Synthesis and evaluation of the substrate activity of C-6 substituted purine ribosides with E. coli purine nucleoside phosphorylase: palladium mediated cross-coupling of organozinc halides with 6-chloropurine nucleosides.

Authors:  Abdalla E A Hassan; Reham A I Abou-Elkhair; James M Riordan; Paula W Allan; William B Parker; Rashmi Khare; William R Waud; John A Montgomery; John A Secrist
Journal:  Eur J Med Chem       Date:  2011-11-04       Impact factor: 6.514

3.  Synthesis and anti-Hantaan virus activity of N(1)-3-fluorophenyl-inosine.

Authors:  Dong-Hoon Chung; J Jacob Strouse; Yanjie Sun; Jeffrey B Arterburn; William B Parker; Colleen B Jonsson
Journal:  Antiviral Res       Date:  2009-04-02       Impact factor: 5.970

4.  C-C cross-coupling reactions of O6-alkyl-2-haloinosine derivatives and a one-pot cross-coupling/O6-deprotection procedure.

Authors:  Venkateshwarlu Gurram; Narender Pottabathini; Ramesh Garlapati; Avinash B Chaudhary; Balaram Patro; Mahesh K Lakshman
Journal:  Chem Asian J       Date:  2012-05-08

5.  Synthesis of a 3'-C-ethynyl-β-d-ribofuranose purine nucleoside library: Discovery of C7-deazapurine analogs as potent antiproliferative nucleosides.

Authors:  Fabian Hulpia; Sam Noppen; Dominique Schols; Graciela Andrei; Robert Snoeck; Sandra Liekens; Peter Vervaeke; Serge Van Calenbergh
Journal:  Eur J Med Chem       Date:  2018-07-29       Impact factor: 6.514

6.  Versatile synthesis and biological evaluation of novel 3'-fluorinated purine nucleosides.

Authors:  Hang Ren; Haoyun An; Paul J Hatala; William C Stevens; Jingchao Tao; Baicheng He
Journal:  Beilstein J Org Chem       Date:  2015-12-09       Impact factor: 2.883

7.  Site-selective remote C(sp3)-H heteroarylation of amides via organic photoredox catalysis.

Authors:  Hui Chen; Wenjing Fan; Xiang-Ai Yuan; Shouyun Yu
Journal:  Nat Commun       Date:  2019-10-18       Impact factor: 14.919

8.  Nucleophilic Arylation of Halopurines Facilitated by Brønsted Acid in Fluoroalcohol.

Authors:  Naoko Takenaga; Toshitaka Shoji; Takayuki Menjo; Akiko Hirai; Shohei Ueda; Kotaro Kikushima; Tomonori Hanasaki; Toshifumi Dohi
Journal:  Molecules       Date:  2019-10-23       Impact factor: 4.411
  8 in total

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