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Literature DB >> 16275078

Synthesis and antiviral activity of 7-deazaneplanocin A against orthopoxviruses (vaccinia and cowpox virus).

Balakumar Arumugham¹, Hyo-Joong Kim, Mark N Prichard, Earl R Kern, Chung K Chu.

Abstract

An efficient method for the synthesis of 7-deazaneplanocin A (2) has been accomplished by the condensation of cyclopentenol 3 with 6-chloro-7-deazapurine followed by subsequent functional group manipulations. The synthesized 7-deazaneplanocin A (2) exhibited potent antiviral activity against cowpox and vaccinia viruses without cytotoxicity in HFF cells.

Entities: Chemical

Mesh：

Substances：

Year: 2005 PMID： 16275078 PMCID： PMC4264103 DOI： 10.1016/j.bmcl.2005.10.007

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.940

17 in total

1. Antiviral activity of cyclopentenyl nucleosides against orthopox viruses (Smallpox, monkeypox and cowpox).

Authors: C K Chu; Y H Jin; R O Baker; J Huggins
Journal: Bioorg Med Chem Lett Date: 2003-01-06 Impact factor: 2.823

2. New neplanocin analogues. 12. Alternative synthesis and antimalarial effect of (6'R)-6'-C-methylneplanocin A, a potent AdoHcy hydrolase inhibitor.

Authors: Satoshi Shuto; Noriaki Minakawa; Satoshi Niizuma; Hye-Sook Kim; Yusuke Wataya; Akira Matsuda
Journal: J Med Chem Date: 2002-01-31 Impact factor: 7.446

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Authors: A Hoshi; M Yoshida; M Iigo; R Tokuzen; K Fukukawa; T Ueda
Journal: J Pharmacobiodyn Date: 1986-02

4. Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.

Authors: G Y Song; V Paul; H Choo; J Morrey; R W Sidwell; R F Schinazi; C K Chu
Journal: J Med Chem Date: 2001-11-08 Impact factor: 7.446

5. 5'-Homoaristeromycin. Synthesis and antiviral activity against orthopox viruses.

Authors: Minmin Yang; Stewart W Schneller
Journal: Bioorg Med Chem Lett Date: 2005-01-03 Impact factor: 2.823

6. Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities.

Authors: C K Tseng; V E Marquez; R W Fuller; B M Goldstein; D R Haines; H McPherson; J L Parsons; W M Shannon; G Arnett; M Hollingshead
Journal: J Med Chem Date: 1989-07 Impact factor: 7.446

7. 5'-Homoneplanocin A inhibits hepatitis B and hepatitis C.

Authors: Minmin Yang; Stewart W Schneller; Brent Korba
Journal: J Med Chem Date: 2005-07-28 Impact factor: 7.446

8. Neplanocin A. A potent inhibitor of S-adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse L929 cells.

Authors: R T Borchardt; B T Keller; U Patel-Thombre
Journal: J Biol Chem Date: 1984-04-10 Impact factor: 5.157

9. Studies on neplanocin A, new antitumor antibiotic. I. Producing organism, isolation and characterization.

Authors: S Yaginuma; N Muto; M Tsujino; Y Sudate; M Hayashi; M Otani
Journal: J Antibiot (Tokyo) Date: 1981-04 Impact factor: 2.649

10. Structure-activity relationship of heterobase-modified 2'-C-methyl ribonucleosides as inhibitors of hepatitis C virus RNA replication.

Authors: Anne B Eldrup; Marija Prhavc; Jennifer Brooks; Balkrishen Bhat; Thazha P Prakash; Quanlai Song; Sanjib Bera; Neelima Bhat; Prasad Dande; P Dan Cook; C Frank Bennett; Steven S Carroll; Richard G Ball; Michele Bosserman; Christine Burlein; Lawrence F Colwell; John F Fay; Osvaldo A Flores; Krista Getty; Robert L LaFemina; Joseph Leone; Malcolm MacCoss; Daniel R McMasters; Joanne E Tomassini; Derek Von Langen; Bohdan Wolanski; David B Olsen
Journal: J Med Chem Date: 2004-10-07 Impact factor: 7.446

4 in total