Literature DB >> 26167667

Design, Synthesis, and Evaluation of Anti-HBV Activity of Hybrid Molecules of Entecavir and Adefovir: Exomethylene Acycloguanine Nucleosides and Their Monophosphate Derivatives.

Shuhei Imoto1, Satoru Kohgo, Ryoh Tokuda, Hiroki Kumamoto, Manabu Aoki, Masayuki Amano, Nobuyo Kuwata-Higashi, Hiroaki Mitsuya, Kazuhiro Haraguchi.   

Abstract

Exomethylene acycloguanine nucleosides 4, 6 and its monophosphate derivatives 5, 7, and 8 have been synthesized. Mitsunobu-type coupling of 2-N-acetyl-6-O-diphenylcarbamoylguanine (11) with primary alcohols proceeded regioselectively to furnish the desired N(9)-substituted products in moderate yield. Evaluation of 4-8 for anti-HBV activity in HepG2 cells revealed that the phosphonate derivative 8 was found to exhibit moderated activity (EC50 value of 0.29 μM), but cytotoxicity (CC50 value of 39 μM) against the host cells was also observed.

Entities:  

Keywords:  Nucleoside; acyclonucleoside; adefovir; anti-HBV activity; entecavir; hybrid; nucleoside phosphonate; pro-drug

Mesh：

Substances：

Year:  2015        PMID： 26167667      PMCID： PMC7712530          DOI： 10.1080/15257770.2015.1037456

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


  11 in total

Review 1.  Entecavir: a review of its use in chronic hepatitis B.

Authors:  Lesley J Scott; Gillian M Keating
Journal:  Drugs       Date:  2009-05-29       Impact factor: 9.546

Review 2.  Hepatitis B virus infection.

Authors:  Jules L Dienstag
Journal:  N Engl J Med       Date:  2008-10-02       Impact factor: 91.245

3.  Ten paths to the discovery of antivirally active nucleoside and nucleotide analogues.

Authors:  Erik De Clercq
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2012-04       Impact factor: 1.381

4.  Synthesis and antiviral evaluation of novel exomethylene acyclic nucleosides and phosphonic acid nucleosides.

Authors:  Aihong Kim; Joon Hee Hong
Journal:  Arch Pharm (Weinheim)       Date:  2005-11       Impact factor: 3.751

5.  Production of hepatitis B virus particles in Hep G2 cells transfected with cloned hepatitis B virus DNA.

Authors:  M A Sells; M L Chen; G Acs
Journal:  Proc Natl Acad Sci U S A       Date:  1987-02       Impact factor: 11.205

6.  Synthesis and antiviral activity of phosphoralaninate derivatives of methylenecyclopropane analogues of nucleosides.

Authors:  Y L Qiu; R G Ptak; J M Breitenbach; J S Lin; Y C Cheng; J C Drach; E R Kern; J Zemlicka
Journal:  Antiviral Res       Date:  1999-08       Impact factor: 5.970

7.  Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus.

Authors:  S F Innaimo; M Seifer; G S Bisacchi; D N Standring; R Zahler; R J Colonno
Journal:  Antimicrob Agents Chemother       Date:  1997-07       Impact factor: 5.938

8.  A novel class of phosphonate nucleosides. 9-[(1-phosphonomethoxycyclopropyl)methyl]guanine as a potent and selective anti-HBV agent.

Authors:  Jong-Ryoo Choi; Dong-Gyu Cho; Kee Y Roh; Jae-Taeg Hwang; Sinbyoung Ahn; Hyun S Jang; Woo-Young Cho; Kyong W Kim; Young-Gyo Cho; Jeongmin Kim; Yong-Zu Kim
Journal:  J Med Chem       Date:  2004-05-20       Impact factor: 7.446

9.  Ester prodrugs of acyclic nucleoside thiophosphonates compared to phosphonates: synthesis, antiviral activity and decomposition study.

Authors:  Loïc Roux; Stéphane Priet; Nadine Payrot; Clément Weck; Maëlenn Fournier; Fabien Zoulim; Jan Balzarini; Bruno Canard; Karine Alvarez
Journal:  Eur J Med Chem       Date:  2013-03-14       Impact factor: 6.514

10.  Replication strategy of human hepatitis B virus.

Authors:  H Will; W Reiser; T Weimer; E Pfaff; M Büscher; R Sprengel; R Cattaneo; H Schaller
Journal:  J Virol       Date:  1987-03       Impact factor: 5.103
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  2 in total

1.  Synthesis and evaluation of the anti-hepatitis B virus activity of 4'-Azido-thymidine analogs and 4'-Azido-2'-deoxy-5-methylcytidine analogs: structural insights for the development of a novel anti-HBV agent.

Authors:  Kengo Onitsuka; Ryoh Tokuda; Nobuyo Kuwata-Higashi; Hiroki Kumamoto; Manabu Aoki; Masayuki Amano; Satoru Kohgo; Debananda Das; Kazuhiro Haraguchi; Hiroaki Mitsuya; Shuhei Imoto
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2019-09-12       Impact factor: 1.381

2.  Discovery of Oxime Ethers as Hepatitis B Virus (HBV) Inhibitors by Docking, Screening and In Vitro Investigation.

Authors:  Jie Tan; Min Zhou; Xinhua Cui; Zhuocai Wei; Wanxing Wei
Journal:  Molecules       Date:  2018-03-12       Impact factor: 4.411
  2 in total

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