103
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis and Antiviral Evaluation of Novel 2,3-Dihydroxypropyl Nucleosides from 2- and 4-Thiouracils

, , , &
Pages 1257-1271 | Received 21 Aug 2007, Accepted 27 Feb 2008, Published online: 26 Nov 2008

REFERENCES

  • Schaeffer , H.J. , Beauchamp , L. , DeMiranda , P. , Elion , G.B. and Bauer , D.J. 1978 . Collins, P. 9-(2-Hydroxyethoxymethyl)guanine activity against viruses of the herpes group . Nature , 272 : 583 – 585 .
  • El Ashry , E.S.H. and El Kilany , Y. 1996 . Acyclonucleosides: Part 1. seco-Nucleosides . Adv. Heterocyc. Chem. , 67 : 391 – 438 .
  • El Ashry , E.S.H. and El Kilany , Y. 1997 . Acyclonucleosides: Part 2. diseco-Nucleosides . Adv. Heterocyc. Chem. , 68 : 1 – 88 .
  • El Ashry , E.S.H. and El Kilany , Y. 1998 . Acyclonucleosides: Part 3. Tri-, tetra-, and pentaseco-nucleosides . Adv. Heterocyc. Chem. , 69 : 129 – 215 .
  • Chu , C.K. and Cutler , S.J. 1986 . Chemistry and antiviral activities of acyclonucleosides . J. Heterocyc. Chem. , 23 : 289 – 319 .
  • Agrofoglio , L.A. and Challang , S.R. 1998 . Acyclic, Carbocyclic and L-Nucleosides , Vol. Acyclic, Carbocyclic and L-Nucleosides , 173 New York, Kluwer Academic .
  • Vandendriessche , F. , Snoeck , R. , Janssen , G. , Hoogmartens , J. , Van Aerschot , A. , De Clercq , E. and Herdwijn , P. 1992 . Synthesis and antiviral activity of acyclic nucleosides with a 3(S),5-dihydroxypentyl or 4(r)-methoxy-3(s),5-dihydroxypentyl side chain . J. Med. Chem. , 35 : 1458 – 1465 .
  • Earnshaw , D.L. , Bacon , T.H. , Darlison , S.J. , Edmonds , K. , Perkins , R.M. and Vere Hodge , R.A. 1992 . Mode of antiviral action of penciclovir in mrc-5 cells infected with herpes simplex Virus type 1 (HSV-1), HSV-2, and varicellazoster virus . Antimicrob. Agents Chemother. , 36 : 2747 – 2757 .
  • Oh , C.H. , Baek , T.R. and Hong , J.H. 2005 . Concise synthesis and antiviral activity of novel unsaturated acyclic pyrimidine nucleosides . Nucleosides, Nucleotides Nucleic Acids , 24 ( 2 ) : 153 – 160 .
  • Lee , J.Y. , Oh , C.H. , Ko , O.H. and Hong , J.H. 2005 . Synthesis and anti-HCMV activity of novel acyclic nucleosides . Nucleosides, Nucleotides Nucleic Acids , 21 ( 10 ) : 709 – 721 .
  • De Clercq , E. , Andrej , G. , Balzarini , J. , Leyssen , P. , Naesens , L. , Neyts , J. , Hocková , D. and Holý , A. 2005 . Antiviral potential of a new generation of acyclic nucleoside phosphonates, the 6-[2-(phosphonomethoxy)alkoxy]-1,4-diaminopyrimidines . Nucleotides Nucleic Acids , 24 ( 5–7 ) : 331 – 341 .
  • De Clercq , E. 1997 . Development of resistance of human immunodeficiency virus (HIV) to anti-HIV agents: How to prevent the problem? . Int. J. Antimicrobiol. Agents , 9 : 21 – 36 .
  • Mellors , J.W. , Rinaldo , C.R. Jr. , Gupta , P. , White , R.M. , Todd , J.A. and Kingsley , L.A. 1996 . Prognosis in HIV-1 infection predicted by the quantity of virus in plasma . Science , 272 : 1167 – 1170 .
  • Pai , S.B. , Liu , S.-H. , Zhu , Y.-L. , Chu , C.K. and Cheng , Y.C. 1996 . Inhibition of hepatitis B virus by a novel L-nucleoside, 2′-fluoro-5-methyl-β-L-arabino-furanosyl uracil . Antimicrob. Agents Chemother , 40 : 380 – 386 .
  • Condreay , L.D. , Jansen , R.W. , Powdrill , T.F. , Johnson , L.C. , Selleseth , D.W. , Paff , M.T. , Daluge , S.M. , Painter , G.R. , Furman , P.A. and Ellis , M.N. 1994 . Averett, D.R. Evaluation of the potent anti-hepatitis B virus agent 1(-) cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine in a novel in vivo model . Antimicrob. Agents Chemother , 38 : 616 – 619 .
  • Tsai , C.-C. , Follis , K.E. , Sabo , A. , Beck , T.W. , Grant , R.F. , Bischofberger , N. , Benveniste , R. and Black , R.E. 1995 . Prevention of SIV infection in macaques by (r)-9-(2-phosphonylmethoxypropyl)adenine . Science , 270 : 1197 – 1199 .
  • Colcacino , J.M. , Malcolm , S.K. and Jaskunas , S.R. 1994 . Effect of fialuridine on replication of mitochondrial DNA in CEM cells and in human hepatoblastoma cells in culture . Antimicrob. Agents Chemother. , 38 : 1997 – 2002 .
  • Chu , C.K. , Ma , T.W. , Shanmuganathan , K. , Wang , C. , Xiang , Y. , Pai , S.B. , Yao , G.-Q. , Sommadossi , J.-P. and Cheng , Y.-C. 1995 . Use of 2′-Fluoro-5-Methyl-β-L-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and Epstein-Barr virus . Antimicrob. Agents Chemother , 39 : 979 – 981 .
  • Lin , T.S. , Lou , M.Z. , Pai , S.B. , Dutschuman , G.E. and Cheng , Y.-C. 1994 . Synthesis and biological evaluation of 2′,3′-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV) . J. Med. Chem. , 37 : 798 – 803 .
  • Doong , S.-L. , Tsai , G.-H. , Shinazi , R.F. , Liotta , D.C. and Cheng , Y.-C . 1991 . Inhibition of the replication of hepatitis B virus in vitro by 2′,3′-dideoxy-3′-thiacytidine and related analogues . Proc. Nat. Acad. Sci. USA , 88 : 8495 – 8499 .
  • Furman , P.A. , Davis , M. , Liotta , D.C. , Paff , M. , Frick , L.W. , Nelson , D.J. , Dornsife , R.E. , Warster , J.A. , Wilson , L.J. , Fyfe , J.A. , Tuttle , J.V. , Miller , W.H. , Condreay , L. , Averett , D.R. , Shinazi , R.F. and Painter , G.R . 1992 . The anti-hepatitis B virus activities, cytotoxicities, and anabolic profiles of the (−) and (+) enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine . Antimicrob. Agents Chemother , 36 : 2686 – 2692 .
  • Naesens , L. , Snoeck , R. , Andrei , G. , Balzarini , J. , Neyts , J. and De Clercq , E. 1997 . HPMPC (cidofovir), PMEA (adefovir) and Related acyclic nucleoside phosphonate analogs: A review of their pharmacology and clinical potential in the treatment of viral infections . Antiviral Chem. Chemother. , : 1 – 23 .
  • De Clercq , E. 1991 . Broad-Spectrum Anti-DNA Virus and Anti-retrovirus activity of phosphonylmethoxyalkylpurines and pyrimidines . Biochem. Pharmacol. , 42 : 963 – 972 .
  • Beach , J.W. , Jeong , L.S. , Alves , A.J. , Pohl , D. , Kim , H.O. , Chang , C.-N. , Doong , S.-L. , Schinazi , R.F. , Cheng , Y.-C. and Chu , C.K. 1992 . Synthesis of enantiomerically pure (2′r,5′s)-(–)-1-[2-(hydroxy-methyl)oxathiolan-5-yl]cytosine as a potent antiviral agent against hepatitis B virus (HBV) and human immunodeficiency virus (HIV) . J. Org. Chem. , 57 : 2217 – 2219 .
  • El Ashry , E.S.H. , Abdel Rahman , A.A.-H. , Rashed , N. and Rasheed , H.A. 1999 . Homoacylovir Analogues of unnatural bases and their activity against hepatitis B virus . Pharmazie , 54 : 893 – 897 .
  • El Ashry , E.S.H. , Abdel Rahman , A.A.-H. , Rashed , N. and Rasheed , H.A. 1999 . Synthesis and anti-hepatitis B virus activity of some 2,3-dihydroxyprop-1-yl unnatural hetaryls . Archives of Pharmazie Pharmaceutical Medicinal Chemistry , 332 : 327 – 330 .
  • Awad , L. and El Ashry , E.S.H. 1998 . Synthesis and conformational analysis of seco C-nucleosides and their diseco double-headed analogues of the 1,2,4-triazole,1,2,4-triazolo[3,4-b]1,3,4-thiadiazole . Carbohydr. Res. , 312 : 9 – 22 .
  • Rashed , N. , Abdel Hamid , H. , Ramadan , E. and El Ashry , E.S.H. 1998 . Acyclo C-Nucleoside analogs. Regioselective annellation of a triazole ring to 5-methyl-1,2,4-triazino[5,6-b]indole and formation of certain 3-polyhydroxyalkyl derivatives . Nucleosides Nucleotides , 17 : 1373 – 1384 .
  • Hamed , A. , Abo-Amaym , E.R. and El Ashry , E.S.H. 1998 . Synthesis of acyclo c-nucleosides of phenanthro[9,10-e][1,2,4]triazino[3,4-c][1,2,4] triazoles, and their precursors . Nucleosides Nucleotides , 17 : 1385 – 1407 .
  • El Ashry , E.S.H. , Abdel-Rahman , A. , Rashed , N. , Awad , L.F. and Rasheed , H.A. 2006 . Synthesis of AZT analogues: 7-(3-Azido-2-hydroxypropyl)-, 7-(3-amino-2-hydroxypropyl)-, 7-(3-triazolyl-2-hydroxypropyl)theophyllines . Nucleosides, Nucleotides Nucleic Acids , 25 : 299 – 305 .
  • El Ashry , E.S.H. , Rashed , N. , Abdel-Rahman , A. , Awad , L.F. and Rasheed , H.A. 2006 . Synthesis of 2-bromomrthyl-3-hydroxy-2-hydroxymethylpropyl pyrimidine and theophylline nucleosides under microwave irradiation. Evaluation of their activity against hepatitis B virus . Nucleosides, Nucleotides Nucleic Acids , 25 : 925 – 939 .
  • Koszytkowska-Stawiń , M. , Kaleta , K. , Sas , W. and De Clercq , E. 2007 . Synthesis and antiviral of aza-analogues of acyclovir . Nucleosides, Nucleotides Nucleic Acids , 26 : 51 – 64 .
  • El Ashry , E.S.H. , Awad , L.F. and Winkler , M. 2000 . A new approach to the synthesis of nucleosides of 1,2,4-triazole . J. Chem. Soc. Perkin Trans. , 1 : 829
  • El Ashry , E.S.H. and Awad , L.F. 2001 . Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine . Nucleoside, Nucleotides Nucleic Acids , 20 : 103 – 116 .
  • Balbaa , M. , Mansour , H. , El-Sawy , H. and El Ashry , E. S.H. 2002 . Inhibition of some hepatic glycosidases by the diseco nucleosides, 4-amino-3-(D-glucopentitol-1-yl)-5-mercapto-1,2,4-triazole and its 3-methyl analog . Nucleosides Nucleotides Nucleic Acids , 21 : 695 – 708 .
  • Abdel-Rahman , A. A.H. , Abdel-megied , A. E.S. , Goda , A. E.S. and El Ashry , E. S.H. 2003 . Synthesis of anti-HBV activity of thiouracils linked via S and N-1 to the 5-position of methyl α-D-ribofuranoside . Nucleosides Nucleotides Nucleic Acids , 22 : 2027 – 2038 .
  • Moustafa , A.H. , Haggam , R.A. , Younes , M.E. and El Ashry , E.S.H. 2005 . Double headed acyclo C-nucleoside analogues. Functionalized 1,2-bis-(1,2,4-triazol-3-yl) thane-1,2-diol . Nucleosides Nucleotides Nucleic Acids , 24 : 1885 – 1894 .
  • El Ashry , E. S. H. , Rashed , N. , Awad , L. F. , Ramadan , E. , Abdel-Mageed , S. M. and Rezki , N. 2007 . Novel Regioselective Synthesis of acyclonucleoside analogues derived from 4,5-diphenylimidazole-2-thione and a competitive intramolecular ring closure of the S-hydroxyalkyl-imidazoles to 1,3-thiazino- and thiazolo[3,2-a]imidazoles, role of catalyst, microwave irradiation and solid support . Nucleosides Nucleotides Nucleic Acids , 26 : 423 – 435 .
  • El Ashry , E. S.H. , Kassem , A.A. , Abdel-Hamid , H. , Louis , F.F. , Khattab , Sh. and Aouad , M.R. 2007 . Novel regioselective synthesis of acyclonucleoside analogues derived from 5-(3-chlorobenzo[b]thien-2-yl)-4H-1,2,4-triazole-3-thiol and a facile synthesis of their triazolo-thiazoles and thiazines. Role of catalyst and MWI . Nucleosides Nucleotides Nucleic Acids , 26 : 437 – 451 .
  • Brown , T.H. , Blakemore , R.C. , Durant , G.J. , Emmett , J.C. , Ganellin , C.R. , Parson , M.E. , Rawlings , D.A. and Walker , T.F. 1988 . Isocytosine H2-receptor histamine antagonists I. Oxmetidine and related compounds . Eur. J. Med. Chem. , 23 : 53 – 62 .
  • Baldwin , J.J. , Raab , A.W. , Mensler , K. , Arison , B.H. and Mcclure , D.E. 1978 . Synthesis of (R)- and (S)-epichlorohydrin . J. Org. Chem. , 43 : 4876 – 4878 .
  • Sells , M.A. , Chen , M.L. and Acs , G. 1987 . Production of hepatitis B virus particles in Hep G2 cells transfected with cloned hepatitis B virus DNA . Proc. Nat. Acad. Sci. USA , 84 : 1005 – 1009 .
  • Korba , B.E. and Gerin , J.L. 1992 . Use of a standardized cell culture assay to assess activities of nucleoside analogs against hepatitis B virus . Antiviral Res. , 19 : 55 – 70 .
  • Fouad , T. , Nielsen , C. , Brunn , L. and Pederson , E.B. 1998 . Use of standardization cell culture assay to assess activities of some potent anti-HIV nucleoside analogues against hepatitis B Virus replication . Sc. J. Az. Med. Fac. (GIRLS) , 19 : 1173 – 1187 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.