New acyclic quinoxaline nucleosides. Synthesis and anti-HIV activity

Nucleosides, Nucleotides and Nucleic Acids

Volumn 27, Issue 2, 2008, Pages 146-156

  Ali, Ibrahim A I ^a   Al Masoudi, Iman A ^b   Aziz, Nazik M ^c   Al Masoudi, Najim A ^c,d  

^a Suez Canal University   (Egypt)

^b UNIVERSITY OF BASRAH   (Iraq)

^c UNIVERSITY OF SULAIMANI   (Iraq)

^d UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Acyclonucleosides; Alkylation; Antiviral activity; Glycosides; Quinoxalines

Indexed keywords

1 (2,3 DIHYDROXYPROPYL) 6,7 DIMETHYL QUINOXALINE 2 ONE; 1 (4,5 DIACETOXYPENTYL) 6,7 DIMETHYLQUINOXALIN 2 ONE; 1 (4,5 DIHYDROPENTYL) 3 METHYLQUINOXALIN 2 ONE; 1 (4,5 DIHYDROPENTYL) 3 PHENYLQUINOXALIN 2 ONE; 1 (4,5 DIHYDROPENTYL)QUINOXALIN 2 ONE; 3,6,7 TRIMETHYL 1 (4,5 DIHYDROXYPENTYL)QUINOXALIN 2 ONE; 5 (2 METHYLQUINOXALIN 3 YLOXY)PENTANE 1,2 DIOL; 5 (2 PHENYLQUINOXALIN 3 YLOXY)PENTANE 1,2 DIOL; 5 (2,6,7 TRIMETHYLQUINOXALIN 3 YLOXY)PENTANE 1,2 DIOL; 5 (2,6,7 TRIPHENYLQUINOXALIN 3 YLOXY)PENTANE 1,2 DIOL; 5 (6,7 DIMETHYLQUINOXALIN 2 YLOXY)PENTANE 1,2 DIOL; 5 (QUINOXALIN 2 YLOXY)PENTANE 1,3 DIOL; 6,7 DIMETHYL 1 (2,2 DIMETHYLDIOXLAN 4 YLMETHYL)QUINOXALIN 2 ONE; 6,7 DIMETHYL 1 (4,5 DIHYDROXYPENTYL) 3 PHENYLQUINOXALIN 2 ONE; 6,7 DIMETHYL 1 (4,5 DIHYDROXYPENTYL)QUINOXALIN 2 ONE; ANTIVIRUS AGENT; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; DRUG HYDROXYLATION; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS; STRUCTURE ACTIVITY RELATION;

ANTI-HIV AGENTS; CELL LINE; DRUG EVALUATION, PRECLINICAL; HIV INFECTIONS; HIV-1; HUMANS; NUCLEOSIDES; QUINOXALINES; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2;

EID: 38349189539     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770701795920     Document Type: Article

References (37)

1. Chu, C.K.; Cutler, S.J. Chemistry and antiviral activities of acyclonucleosides. J. Heterocycl. Chem. 1986, 23, 289-319.
2. Remy, R.J.; Secrist, III, J.A. Acyclic nucleosides other than acyclovir as potential antiviral agents. Nucleosides Nucleotides 1985, 4, 411-427.
3. Miyasaka, T.; Tanaka, H.; Baba, M.; Hayakawa, H.; Walker, R.T.; Balzarini, J.; De Clercq, E. A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 1989, 32, 2507-2509.
4. Tanaka, H.; Miyasaka, T.; Sekiya, K.; Takashima, H.; Ubasawa, M.; Nitta, I.; Baba, M.; Walker, R.T.; DeClercq, E. Synthesis of some analogues of 1-[(2-hydroxyethoxy) methyl]-6-(phenylthio)thymine (HEPT) which have different types of acyclo structure. Nucleotides 1992, 11, 447-456.
5. Elion, G.B.; Furman, J.A.; Fyfe, J.A.; deMiranda, P.; Beauchamp, L.; Schaeffer, H. Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl)guanine. J. Proc. Natl. Acad. Sci. USA 1977, 74, 5716-5720.
6. Schaefer, H.J.; Beauchamp, L.; deMiranda, P.; Elion, G.B.; Bauer, D.J.; Collins, P. 9-(2-Hydroxyethoxymethyl)guanine activity against viruses of the herpes group. Nature (London) 1978, 272, 583-585.
7. a) Fiddian, A.P.; Brigden, D.; Yeo, J.M.; Hickmott, E.A. Acyclovir: An update of the clinical applications of this antiherpes agent. Antiviral Res. 1984, 4, 99-177;
8. b) Dollins, R. Antiviral chemotherapy and chemoprophylaxis. Science 1985, 227, 1296-1303;
9. c) Collins, P.; Oliver, N.M. Comparison of the in vitro and in vivo antiherpes virus activities of the acyclic nucleosides, acyclovir (Zovirax) and 9-[(2-hydroxy-1-hydroxymethylethoxy)methyl]guanine (BWB759U). Antiviral Res.1985, 5, 145-156.
10. Lavelle, C.L.B. Acyclovirl is it effective virostatic agent for oral infections? J . Oral Path. Med. 1993, 22, 391-401.
11. Holy, A. Phosphonylmethyl analogs of nucleotides and their derivatives: Chemistry and biology. Nucleosides Nucleotides 1987, 6, 147-155; references cited therein.
12. Keller, P.M.; Fyfe, J.A.; Beauchamp, L.; Lubbers, C.M.; Furman, P.A.; Schaeffer, H.J.; Elion, G.B. Enzymetic phosphorylation of acyclic nucleoside analogs and correlations ith antiherpetic activities. Biochem. Pharmacol. 1981, 30, 3071-3077.
13. Larsson, A.; Alenius, S.; Johansson, N.-G.; Oberg, B. Antiherpetic activity and mechanism of action of 9-(4-hydroxybutyl)guanine. Antiviral Res. 1983, 3, 77-86.
14. Barrio, J.R.; Bryant, J.D.; Keyser, G.E. A direct method for the preparation of 2-hydroxyethoxymethyl derivatives of guanine, adenine, and cytosine. J. Med. Chem. 1980, 23, 572-574.
15. a) El-Ashry, E.S.H.; El Kilany, Y. Acyclonulceolsides: part 1. seco-Nucleosides. Adv. Heterocycl. Chem. 1996, 67, 391-438;
16. b) El-Ashry, E.S.H.; El Kilany, Y. Acyclonulceolsides: part 2. diseco-Nucleosides. Adv. Heterocycl. Chem. 1997, 68, 1-88;
17. c) El-Ashry, E.S.H.; El Kilany, Y. Acyclonulceolsides: part 3. triseco-Nucleosides. Adv. Heterocycl. Chem. 1998, 69, 129-215.
18. Kim, K.S.; Bird, L.Q.; Kickinson, K.E.; Moreland, S.; Schaeffer, T.R.; Waldron, T.; Delany, C.L.; Weller, H.N.; Miller, A.V. Quinoxaline N-oxide containing potent angiotensin II receptor antagonists: synthesis, biological properties, and structure-activity relationships. J. Med. Chem. 1993, 36, 2335-2342.
19. Bandy, R.B.; Greenblatt, L.P.; Jirkovsky, I.L.; Conklin, M.; Russo, R.J.; Bramlett, D.R.; Emrey, T.A.; Simmonds, J.T.; Kowal, D.M.; Stein, R.P.; Tasse, R.P. Potent quinoxaline-spaced phosphono. α-amino acids of the AP-6 type as competitive NMDA antagonists: synthesis and biological evaluation. J. Med. Chem. 1993, 36, 331-342.
20. Ismail, M.M.; Ammar, Y.A.; Ibrahim, M.K.; El-Zahaby, H.S.; Mahmoud, S. Synthesis and pharmacological evaluation of novel quinoxalines as potential nonulcerogenic anti-inflammatory and analgesic agents. Arzneim.-Forsch. 2005, 55, 738-743.
21. Sarges, R.; Howard, H.R.; Browne, R.G.; Lebel, L.A.; Seymour, P.A.; Koe, B.K. 4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants. J. Med. Chem. 1990, 33, 2240-2254.
22. Hazeldine, S.T.; Polin, L.; Kushner, J.; Paluch, J.; White, K.; Edelstein, M.; Palomino, E.; Corbett, T.H.; Horwitz, J.P. Design, synthesis, and biological evaluation of analogues of the antitumor agent, 2-(4-[(7-chloro-2- quinoxalinyl)oxy]phenoxy)propionic acid (XK469). J. Med. Chem. 2001, 44, 1758-1776.
23. Fisherman, J.S.; Osborn, B.L.; Chun, H.G.; Plowman, J.; Smith, A.C.; Christian, M.C.; Zaharko, D.S.; Shoemaker, R.H. Chloroquinoxaline sulfonamide: a sulfanilamide antitumor agent entering clinical trials. Invest. New Drugs 1993, 11, 1-9.
24. El Ashry, E.S.H.; Abdel-Rahman, A.A.H.; Rashed, N.; Rasheed, H.A. Homoacyclovir analogues of unnatural bases and their activity against Hepatitis B virus. Pharmazie 1993, 54, 893-997.
25. Ali, I.A.I.; Fathalla, W. N′-Allyl-2-substituted-6,7-dimethyl-1,2- dihydro-2-quinoxalinone as key intermediate for new acyclonucleosides and their regiosomer O-analogues. Heteroatom Chem. 2006, 17, 280-288.
26. Ali, I.A.I.; Al-Masoudi, I.A.; Hassan, H.Gh.; Al-Masoudi, N.A. Synthesis and anti-HIV activity of new homo acyclic nucleosides, 1-(pent-4-enyl) quinoxaline-2-ones and 2-(pent-4-enyloxy)quinaloxines. Chem. Heterocycl. Comp. 2007, 482, 1242-1250.
27. Al-Masoudi, N.A.; Al-Soud, Y.A.; Eherman, M.; De Clercq, E. Synthesis of acyclic nucleoside analogues of 6,7-dihaloquinolones as potential antibacterial and antiviral agents. Bioog. Med. Chem. 2000, 8, 1407-1413.
28. Al-Masoudi, N.A.; Al-Soud, Y.A.; Geyer, A. Synthesis and spectroscopic analysis of some acyclic C-nucleosides and the homo-C-analogues from 1-(chloroalkyl)-1-aza-2-azoniaallene salts. Tetrahedron 1999, 15, 751-758.
29. Al-Masoudi, N.A.; Al-Soud, Y.A. N- and C-acyclothiocnucleosides of 1,2,3-triazoles. Heteroatom Chem. 2004, 15, 380-387.
30. Nicols, C.J.; Taylor, M.R. The sharpless asymmetric dihydroxylation in the organic chemistry majors laboratory. J. Chem. Ed. 2005, 82, 105-108.
31. Bax, A.; Griffey, R.H.; Hawkins, B.L. Correlation of proton and nitrogen-15 chemical shifts by multiple quantum NMR. J. Magn. Reson. 1983, 55, 301-315.
32. 13C-NMR study of some 6,7-dihaloquinolone nucleosides and their derivatives. Spectroscopy Lett 1998, 31, 1031-1038.
33. Willker, W.; Leibfritz, D.; Kerssebaum, R.; Bermel, W. Gradient selection in inverse heteronuclear correlation spectroscopy. Mag. Reson. Chem. 31, 287-292.
34. El Ashry, E.S.H.; Abdel-Rahman, A.A.-H.; Rashid, N.; Rasheed, H.A. Arch. Pharm. Pharm. Med. Chem. 1999,, 327-330.
35. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods 1988, 20, 309-321.
36. Young, S.D.; Britcher, S.F.; Tran, L.O.; Payne, L.S.; Lumma, W.C.; Lyle, T.A.; Huff, J.R.; Anderson, P.S.; Olsen, D.B.; Carroll, S.S.; Pettibone, D.J.; Obrien, J.A.; Ball, R.G.; Balani, S.K.; Lin, J.H.; Chen, I.W.; Schleif, W.A.; Sardana, V.V.; Long, W.J.; Byrnes, V.W.; Emini, E.A. Novel, highly potent nonnucleoside inhibitor of the human immunodeficiency-virus type-1 reverse transcriptase. Antimicrob. Agents Chemother. 1995, 39, 2602-2605.
37. Fujiwara, T.; Sato, A.; El-Farrash, M.; Miki, S.; Kabe, K.; Isaka, Y.; Kodama, M.; Wu, Y.M.; Chen, L.B.; Harada, H.; Sugimoto, H.; Hatanaka, M.; Hinuma, Y. Capravirine (AG-1549): Non-nucleosides RTI. Antimicrob. Agents. Chemother. 1998, 42, 1340-1345.