Synthesis of novel acyclic nucleoside analogues with anti-retroviral activity

Nucleosides, Nucleotides and Nucleic Acids

Volumn 29, Issue 9, 2010, Pages 707-720

  Paju, A ^a   Pari M ^a   Selyutina, A ^b   Zusinaite E ^b   Merits, A ^b   Pehk, T ^c   Siirde, K ^d   Muurisepp A M ^a   Kailas, T ^a   Lopp, M ^a  

^a TALLINN UNIVERSITY OF TECHNOLOGY   (Estonia)

^b UNIVERSITY OF TARTU   (Estonia)

^c NATIONAL INSTITUTE OF CHEMICAL PHYSICS AND BIOPHYSICS   (Estonia)

^d Department of Immunotherapy   (Estonia)

Author keywords

Acyclic nucleosides; anti retroviral activity; hepatitis C virus; human immunodeficiency virus type 1

Indexed keywords

ANTIRETROVIRUS AGENT; CYCLOPENTADIENE DERIVATIVE; GAMMA LACTONE DERIVATIVE; LAMIVUDINE; NUCLEOSIDE ANALOG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; ASYMMETRIC SYNTHESIS; CELL STRAIN MCF 7; CELL VIABILITY; CHIRALITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOMER; HELA CELL; HEPATITIS C VIRUS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; MITSUNOBU REACTION; NONHUMAN; OXIDATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANTI-HIV AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; ELECTRONS; HIV; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LACTONES; NUCLEOSIDES; SOLUBILITY; STEREOISOMERISM;

HEPATITIS C VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 77955614368     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2010.501776     Document Type: Article

References (46)

1. Elion, G.B.; Furman, P.A.; Fyfe, J.A.; De Miranda, P.; Beuchamp, L.; Scaeffer, H.J. Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl)guanine. Proc. Natl. Acad. Sci. USA 1977, 74, 5716-5720.
2. De Clercq, E.; Field, H.J. Antiviral prodrugs-the development of successful prodrug strategies for antiviral chemotherapy. British J. Pharmacol. 2006, 147, 1-11.
3. De Clercq, E. Antiviral drugs in current clinical use. J. Clin. Virol. 2004, 30, 115-133.
4. Griffiths, P.D. Antivirals in the transplant setting. Antiviral Res. 2006, 71, 192-200.
5. Hostetler, K.Y. Alkoxyalkyl prodrugs of acyclic nucleoside phosphonates enhance oral antiviral activity and reduce toxicity: Current state of the art. Antiviral. Res. 2009, 82, A84-A98.
6. Gao, H.; Mitra, A.K. Synthesis of acyclovir, ganciclovir and their podrugs: A review. Synthesis 2000, 329-351.
7. Huryn, D.M.; Okabe, M. AIDS-driven nucleoside chemistry. Chem. Rev. 1992, 92, 1745-1768.
8. Kumamoto, H.; Topalis, D.; Broggi, J.; Pradere, U.; Roy, V.; Berteina-Raboin, S.; Nolan, S.P.; Deville-Bonne, D.; Andrei, G.; Snoeck, R.; Garin, D.; Crance, J.-M.; Agrofoglio, L.A. Preparation of acyclo nucleoside phosphonate analogues based on cross-metathesis. Tetrahedron 2008, 64, 3517-3526.
9. Koszytkowska-Stawinska, M.; Sas, W.; De Clercq, E. Synthesis of aza-analogues of Ganciclovir. Tetrahedron 2006, 62, 10325-10331.
10. Agrofoglio, L.A. An overview of diazine nucleoside analogues. Curr. Org. Chem. 2006, 10, 333-362.
11. Mathe, C; Gosselin, G. L-Nucleoside enantiomers as antiviral drugs: A mini-review. Antiviral Res. 2006,71, 276-281.
12. Zemlicka,J. Enantioselectivity of the antiviral effects of nucleoside analogues. Pharmacology & Ther-apeutics 2000, 85, 251-266.
13. Balzarini, J.; Holy, A.; Jindrich, J.; Naesens, L.; Snoeck, R.; Schols, D.; De Clercq, E. Differential antivirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: Potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)- 2,6-diaminopurine. Antimicrob. Agents Chemother. 1993, 37, 332-338.
14. Boto, A.; Hernandes, D.; Hernandes, R.; Alvares, E. One-pot synthesis of acyclic nucleosides from carbohydrate derivatives, by combination of tandem and sequential reactions.J. Org. Chem. 2007, 72, 9523-9532.
15. Zakirova, N.F.; Shipitsyn, A.V.; Belanov, E.F.;Jasko, M.V. An approach to the synthesis of optically active alkylated adenine derivatives. Bioorg. Med. Chem. Lett. 2004, 14, 3357-3360.
16. Vrbkova, S.; Dracinsky, M.; Holy, A. Bifunctional acyclic nucleoside phosphonates: synthesis of chiral 9-{3-hydroxy[1,4-bis(phosphonomethoxy)]butan- 2-yl} derivatives of purines. Tetrahedron: Asymmetry 2007,18, 2233-2247.
17. /-trihydroxybutyl)adenine derivatives from L-ascorbic and D-isoascorbic acids. Tetrahedron 2003, 59, 6075-6081.
18. Lee, J.; Oh, C.H.; Ko, O.H.; Hong, J.H. Synthesis and anti-HCMV activity of novel acyclic nucleosides. Nucleosides, Nucleotides & Nucleic Acids 2002, 21, 709-721.
19. Hirota, K.; Monguchi, Y; Sajiki, H.; Sako, M.; Kitade, Y. Novel synthesis of purine acyclonucleo-sides possessing a chiral 9-hydroxyalkyl group by sugar modification of 9-D-ribitylpurines. J. Chem. Soc.,Perkin Trans. 1 1998, 941-946.
20. Ali, I.A.I.; Al-Masoudi, I.A.; Aziz, N.M.; Al-Masoudi, N.A. New acyclic quinoxaline nucleosides. Synthesis and anti-HIV activity. Nucleosides, Nucleotides Nucleic Acids 2008, 27, 146-156.
21. Ewing, D.F.; Glacon, V.; Len, C; MacKenzie, G. Synthesis, conformation and antiviral activity of nucleoside analogues with the (2-hydroxy-1- phenylethoxy)methyl glycone\a family of nucleoside analogues related to d4T and aciclovir. New. J. Chem. 2005, 29, 1461-1468.
22. He, L.; Liu, Y; Zhang, W.; Li, M.; Chen, Q. Highly enantioselective synthesis and potential biological activity of chiral novel nucleoside analogues containing adenine and naturally phenol derivatives. Tetrahedron 2005, 65, 8505-8511.
23. Paju, A.; Kanger, T.; Pehk, T.; Lopp, M. Asymmetric oxidation of 1,2-cyclopentenediones. Tetrahedron Lett., 2000, 41, 6883-6887.
24. Paju, A.; Kanger, T.; Pehk, T.; Lindmaa, R.; Müürisepp, A.-M.; Lopp, M. Asymmetric oxidation of 3-alkyl-1,2-cyclopentanediones. Part 2: Oxidative ring cleavage of 3-alkyl-1,2-cyclopentanediones: synthesis of 2-alkyl-y-lactone acids. Tetrahedron: Asymmt. 2003, 14, 1565-1573.
25. /-dideoxynucleoside analogues from 3-benzyl-2-hydroxy- 2-cyclopenten-1-one. Tetrahedron: Asymmetry 2008, 19, 628-634.
26. /-dideoxy- nucleoside analogues. Tetrahedron 2009, 65, 2959-2965.
27. /- dideoxynucleosides. Proc. Natl. Acad. Sci. USA 1986, 83, 1911-1915.
28. /-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro. Biochem. Biophys. Res. Com-mun. 1987, 142, 128-134.
29. Mansuri, M.M.; StarrettJr.,J.E.; Ghazzouli, I.; Hitchcock, M.J.M.; Sterzycki, R.Z.; Brankovan, V.; Lin, T.-S.;August, E.M.; Prusoff, W.H.; Sommadossi, J.-P.; Martin, J.C. 1-(2,3-Dideoxy-/?-D-glycero-pent-2-enofuranosyl) thymine. A highly potent and selective anti-HIV agent.J. Med. Chem. 1989, 32, 461-466.
30. Mitsua, H.; Weinhold, K.J.; Furman, P.A.; St. Clair, M.H.; Lehrman, S.N.; Gallo, R.C.; Bolognesi, D.; Barry, D.W.; Broder, S. 3'-Azido-3'-deoxythymidine (BW A509U): An antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotrophic virus type III/lymphadenopathy-associated virus in vitroin vitro. Proc. Natl. Acad. Sci. USA 1985, 82, 7096-7100.
31. Paju, A.; Laos, M.; Jogi, A.; Pari, M.; Jaälaid, R.; Pehk, T.; Kanger, T.; Lopp, M. Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid y-lactones. Tetrahedron Lett. 2006, 74, 4491-4493.
32. /C-methyl thymidine and 4'C-ethyl thymidine block DNA synthesis by wild-type HIV-1 RT and excision proficient NRTI resistant RT variants. J. Mol. Biol. 2007, 371, 873-882.
33. Nomura, M.; Shuto, S.; Tanaka, M.; Sasaki, T.; Mori, S.; Shigeta, S.; Matsuda, A. Nucleosides and nucleotides. 185. Synthesis and biological activities of 4'a-C-branched-chain sugar pyrimidine nucleosides.J. Med. Chem. 1999, 42, 2901-2908.
34. Keck, G.E.; Andrus, M.B.; Romer, D.R. A useful new enantiomerically pure synthon from malic acid: Chelation-controlled activation as a route to regioselectivity.J. Org. Chem. 1991, 56, 417-420.
35. Taber, D.F.; Sahli, A.; Yu, H.; Meagley, R.P. Efficient intramolecular C-H insertion by an alkylidene carbene generated from a vinyl chloride.J. Org. Chem. 1995, 60, 6571-6573.
36. Cruickshank, K.A.; Jiricny, J.; Reese, C.B. The benzoylation of uracil and thymine. Tetrahedron Lett. 1984, 25, 681-684.
37. Mitsunobu, O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis 1981, 1-28.
38. /-deoxy-carbocyclic thymidine: a difluoromethylidene analogue of promising anti-HIV agent Ed4T. Tetrahedron 2009, 65, 7630-7636.
39. Yang, M.; Zhou, J.; Schneller, S.W. The Mitsunobu reaction in preparing 3-deazapurine carbocyclic nucleosides. Tetrahedron 2006, 62, 1295-1300.
40. Jin, Y.H.; Liu, P.; Wang, J.; Baker, R.; Huggins, J.; Chu, C.K. Practical synthesis of D-and L-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus).J. Org. Chem. 2003, 68, 9012-9018.
41. Dolakova, P.; Dracinsky, M.;Jindrich, F.; Holy, A. Synthesis of analogues of acyclic nucleoside diphosphates containing a (phosphonomethyl)phosphanyl moiety and studies of their phosphorylation. Eur. J. Org. Chem. 2009, 1082-1092.
42. Choo, H.; Beadle, J.R.; Chong, Y; Trahan,J.; Hostetler, K.Y. Synthesis of the 5-phosphono-pent-2-en-1-yl nucleosides: A new class of antiviral acyclic nucleoside phosphonates. Bioorg. Med. Chem. 2007, 15, 1771-1779.
43. Hubert, C; Alexandre, C; Aubertin, A.-M.; Huet, F. An efficient synthesis of dienic nucleoside analogues via a Mitsunobu reaction. Tetrahedron 2003, 59, 3127-3130.
44. /-difluorocytidine. J. Med. Chem. 2009, 52, 2971-2978.
45. Zhu, R.; Wang, M.; Xia, Y; Qu, F.; Neyts, J.; Peng, L. Arylethynyltriazol acyclonucleosides inhibit hepatitis C virus replication. Bioorg. Med. Chem. Lett. 2008, 18, 3321-3327.
46. ; End of the Hepatitis C Virus Genome Essential for RNA Replication.J. Virol. 2005, 79, 380-392.