Synthesis and preliminary biological activity of some new pyrazole derivatives as acyclonucleoside analogues

Letters in Drug Design and Discovery

Volumn 7, Issue 1, 2010, Pages 27-30

  Radi, Smaail ^a   Salhi, Souad ^a   Radi, Amal ^a  

^a FACULTÉ DES SCIENCES   (Morocco)

Author keywords

Acyclonucleoside; Biological activity; Pyrazole; Synthesis

Indexed keywords

ACYCLIC NUCLEOSIDE; PYRAZOLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 77949754130     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018010789869307     Document Type: Article

References (31)

1. Tewari, A.K.; Mishra, A. Synthesis and anti-inflammatory activities of N4,N5-disubstituted-3-methyl-1H-pyrazolo[3,4-c]pyridazines. Bioorg. Med. Chem., 2001, 9, 715-718.
2. Wiley, R.H.; Wiley, P. Pyrazolones, Pyrazolidones and Derivatives; John Wiley and Sons: New York, 1964.
3. Pimerova, E.V.; Voronina, E.V. Antimicrobial activity of pyrazoles and pyridazines obtained by interaction of 4-aryl-3-arylhydrazono-2,4-dioxobutanoic acids and their esters with hydrazines. Pharm. Chem. J., 2001, 35, 18-20.
4. Janus, S.L.; Magdif, A.Z.; Erik, B.P.; Claus, N. Synthesis of triazenopyrazole derivatives as potential inhibitors of HIV-1. Monatsh. Chem., 1999, 130, 1167-1174.
5. Park, H.J.; Lee, K.; Park, S.; Ahn, B.; Lee, J.C.; Cho, H.Y.; Lee, K.I. Identification of antitumor activity of pyrazole oxime ethers. Bioorg. Med. Chem. Lett., 2005, 15, 3307-3312.
6. Bouabdallah, I.; M'barek, L.A.; Zyad, A.; Ramadan, A.; Zidane, I.; Melhaoui, A. Anticancer effect of three pyrazole derivatives. Nat. Prod. Res., 2006, 20, 1024-1030.
7. Michon, V.; Du Penhoat, C.H.; Tombret, F.; Gillardin, J.M.; Lepagez, F.; Berthon, L. Preparation, structural analysis and anticonvulsant activity of 3-and 5-aminopyrazole N-benzoyl derivatives. Eur. J. Med. Chem., 1995, 147-155.
8. Yildirim, I.; Ozdemir, N.; Akçamur, Y.; Dinçer, M.; Andaç, O. 4-Benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid methanol solvate. Acta Cryst., 2005, E61, 256-258.
9. Bailey, D.M.; Hansen, P.E.; Hlavac, A.G.; Baizman, E.R.; Pearl, J.; Defelice, A.F.; Feigenson, M.E. 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants. J. Med. Chem., 1985, 28, 256-260.
10. Chu, C.K.; Cutler, J. Chemistry and antiviral activities of acyclonucleosides. J. Heterocycl. Chem., 1986, 23, 289-319.
11. Arrieta, A.; Carrillo, J.R.; Cossío, F.P.; Ortiz, A.D.; Gomez-Escalonilla, M.J.; de la Hoz, A.; Langa, F.; Moreno, A. Efficient tautomerization hydrazone-azomethine imine under microwave irradiation. Synthesis of [4,3′] and [5,3′]bipyrazoles. Tetrahedron, 1998, 54, 13167-13180.
12. Remy, R.J.; Secrist III, J.A. Acyclic nucleosides other than acyclovir as potential antiviral agents. Nucleosides Nucleotides, 1985, 4, 411-427.
13. Shaeffer, H.J.; Beauchamp, L.; De Miranda, P.; Elion, G.B.; Bauer, D.B., Collins, P. 9-(2-Hydroxyethoxymethyl) guanine activity against viruses of the herpes group. Nature (London), 1978, 272, 583-585.
14. Agrofoglio, L.A.; Challand, S.R. Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic Publishers, USA 1998.
15. Ogilvie, K.K.; Cheriyan, U.O.; Radatus, B.K.; Smith, K.O.; Galloway, K.S.; Kennell, W.L. Biologically active acyclonucleoside analogues. II. The synthesis of 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]guanine (BIOLF-62). Can. J. Chem., 1982, 60, 3005-3010.
16. Field, A.K.; Davie, M.E.; Dewitt, C.; Perry, H.C.; Liou, R., Germershausen, J.I.; Karkas, J.D.; Ashton, W.T.; Johnson, D.B.R.; Tolman, R.C. 9-([2-hydroxy-1-(hydroxymethyl)ethoxy]methyl)guanine: a selective inhibitor of herpes group virus replication. Proc. Natl. Acad. Sci. USA, 1983, 80, 4139-4143.
17. Martin, J.C.; Dvorak, C.A; Smee, D.F.; Mattews T.R.; Verheyden, J.P.H. 9-[(1,3-Dihydroxy-2-propoxy)methyl] guanine: a new potent and selective antiherpes agent. J. Med. Chem.,1983, 26, 759-761.
18. Ashton, W.T.; Canning, L.D.; Reynolds, G.F.; Tolman, R.L.; Karkas, J.D.; Liou, R., Davies, M.-E.M.; De Witt, C.M.; Perry H.C.; Field, A.K. Synthesis and antiherpetic activity of (S)-, (R)-, and (±)-9-[(2,3-dihydroxy-1-propoxy) methyl]guanine, linear isomers of 2′-nor-2′-deoxyguanosine. J. Med. Chem., 1985, 28, 926-933.
19. Lin, T.-S.; Lin, M.-C. Synthesis of 9-(2,3-dihydroxy-1-propoxymethyl) guanine. A new potential antiviral agent. Tetrahedron Lett. 1984, 25, 905-906.
20. Mac Coss, M.; Chen, A.; Tolman, R.L. Syntheses of all four possible diastereomers of the acyclonucleoside 9-(1,3,4-trihydroxy-2-butoxymethyl) guanine from carbohydrate precursors. Tetrahedron Lett., 1985, 26, 4287-4290.
21. Vere Hodge, R.A. Famciclovir and penciclovir. The mode of action of famciclovir including its conversion to penciclovir. Antiviral Chem. Chemother., 1993, 4, 67-84.
22. El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides: Part 1. Seco-Nucleosides. Adv. Heterocycl. Chem., 1997, 67, 391-438.
23. El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides: Part 2. diseco-Nucleosides. Adv. Heterocycl. Chem., 1997, 68, 1-88.
24. El Ashry, E.S.H.; El Kilany, Y. Acyclonucleosides, Part III. tri-, tetra-, and pentaseco-Nucleosides. Adv. Heterocycl. Chem., 1997, 69, 129-215.
25. Robins, M.J.; Hatfield, P.W. Nucleic acid related compounds. 37. Convenient and high-yield syntheses of N-[2-hydroxyethoxy)methyl]heterocycles as acrylic nucleoside analogues. Can. J. Chem., 1982, 60, 547-553.
26. Taha, M.L.; Lazrek, H.B. Synthesis of some 4-substituted 1-(4-hydroxybutyl)-pyrazolo[3,4-d]pyrimidines analogs of 9-(4-hydroxybutyl) guanine (HBG). Bull. Soc. Chim. Belg., 1995, 104, 647-652.
27. Fifani, J.; Ramdani, A.; Tarrago, G. 1,6,11,16-tetraazaporphyrinogen, synthesis and behaviour. New J. Chem., 1977, 1, 521-528.
28. Driessen, W. L. Synthesis of some new pyrazole-containing chelating agents. Recl. Trav. Chim. Pays-Bas, 1982, 101, 441-443.
29. Evans, I.R.; Szécsényi, K.M.; Leovac V.M. 1-(Hydroxymethyl)-3,5-dimethylpyrazole. Acta Cryst., 2005, E61, 625-626.
30. Touzani, R.; Ramdani, A.; El Kadiri, S.; Gourand, F. 1-Hydroxymethyl-3- ethoxy-5-methylpyrazole. Molecules, 1999, 4, M116.
31. Carrod, L.P.; Grady, F.D. Antibiotics and Chemotherapy, 3rd ed.; Churchill Livingstone: Edin-burgh, 1972, pp. 477.S