Theoretical investigation of 3′-subtituted-2′-3′- dideoxythymidines related to AZT. QSAR infrared and substituent electronic effect studies

Arkivoc

Volumn 2008, Issue 13, 2008, Pages 255-265

  Essa, Ali Hashem ^a   Ibrahim, Medhat ^b   Hameed, Ali Jameel ^a   Al Masoudi, Najim A ^c  

^a UNIVERSITY OF BASRAH   (Iraq)

^b NATIONAL RESEARCH CENTRE   (Egypt)

^c UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

3 azido 2 ,3 dideoxythymidine (AZT); Hammett's equation; Infrared study; QSAR; Substituent electronic effects

Indexed keywords

EID: 49949103969     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.d28     Document Type: Article

References (30)

1. Arion, D.; Kaushik, N.; McCormick, N.; Borkow, G.; Parniak, M. A. Biochemistry 1998, 37, 15908.
2. Zhang, R.; Lu, Z.; Diasio, C. R.; Liu, T.; Soong, S.-J. Antimicrob. Agents Chemother. 1993, 37, 1771.
3. Fischl, M. A.; Richman, D. D.; Grieco, M. H.; Gottlieb, M. S.; Volberding, P. A.; Laskin, O. L.; Leedom, J. M.; Groopman, J. E.; Mildvan, D.; Schooley, R. T.; Jackson, G. G.; Durack, D. T.; King, D. N. Engl. J. Med. 1987, 317, 185.
4. Adams, D. R.; Maillard, Ca. P. M.; Florent, J.; Evers, M.; He'nin, Y.; Litvak, S.; Litvak, J. L.; Monneret, J. C.; Grierson, D. S. J. Med. Chem. 1997, 40, 1550.
5. Herdewijn, P.; De Clercq, E. In: Design of Anti-Aids Drugs; De Clercq, E., Eds.; Elsevier Amsterdam, 1990; p 141.
6. (a) Richman, D. D. Annu. Rev. Pharmacol. Toxicol. 1993, 32, 149.
7. (b) De Clereq, E. Biochem. Pharmacol. 1994, 47, 155.
8. (c) Larder, B. A.; Kemp, S. D. Science 1989, 246, 1155.
9. Nasr, M.; Litterest, C.; McGowan, J. Antiviral Res. 1990, 14, 125.
10. Maillard, M.; Florent, J.-C.; Lemaitre, M.; Begassat, F.; Bugnicourt, A.; Ferrieux, C.; Rombi, C.; Pacaud, E. D.; Thierry, D. E.; Zerial, A.; Monneret, C.; Grierson, D. S. Bioorg. Med. Chem. Lett. 1992, 2, 1469.
11. Kitade, Y.; Suzuki, A.; Hirota, K.; Maki, Y.; Nakane, H.; Ono, K.; Baba, M.; Shigeta, S. Chem. Pharm. Bull. 1992, 40, 920.
12. Sato, Y.; Utsumi, K.; Maruyama, T.; Kimura, T.; Yamamoto, I.; Richman, D. D. Chem. Pharm. Bull. 1994, 42, 595.
13. Yamamoto, I.; Kimura, T.; Tateoka, Y.; Watanabe, K.; Ho, I. K. J. Med. Chem. 1987, 30, 2227.
14. Al-Masoudi, N. A.; Al-Soud, Y. A.; Ali, I. A. I.; Schuppler, T.; Pannecouque, Ch.; De Clercq, E. Nucleosides Nucleosides Nucleic Acids 2007, 26, 223.
15. Huff, A. C.; Topal, M. D. J. Biol. Chem. 1987, 262, 12843.
16. Essa, A. H.; Al-Masoudi, N. A. J. Comput. Theor. Nanoscience 2008, in press.
17. MOPAC 2002 Version 2.5.3, J. J. P. Stewart, Fujitsu Limited, Tokyo, Japan.
18. Topacli, C.; Topacli, A.; Tes,neli, B.; Richardson, T.; Gümüs, G.; Ahsen, V. Vibrational Spectrosc. 2006, 40, 20.
19. Byler, M.; Susi, H., Biopolymers 1986, 25, 469.
20. Bouwstra, J. A.; Dubbelear, F. E. R.; Gooris, G. S.; Ponec, M. Acta Derm.-Venereol. 2000, 208, 23.
21. Gaudreau, S.; Neault, J. F.; Tajmir-Riahi, H. A. J. Biomolec. Struct. Dyn. 2002, 19, 1007.
22. Narishetty, S. T. K.; Panchagnula, R. J. Control. Release 2005, 102, 59.
23. Wu Y. D.; Wong C. L. J. Org. Chem. 1995, 60, 821.
24. Hayase S., Hrovat, D. A.; Borden W. T. J. Am. Chem. Soc. 2004, 126, 10028.
25. Essa A. H. Intern. J. Quan. Chem. 2007, 107, 1574.
26. Hansch, C.; Leo, A.; Taft R. W. Chem Rev. 1991, 91, 165.
27. Jovanović, S.; Mijin, D.; Mišić-Vuković, M. ARKIVOC 2006, (x), 116.
28. Nifantiev, E. E.; Grachev, M. K.; Burmistrov, S. Y., Chem. Rev. 2000, 100, 3755.
29. Hansch, C.; Leo, A. Exploring QSAR: Fundamentals and applications in chemistry and biology, American Chemical Society: Washington, DC, 1995.
30. Atkin, P. W.; de Paula, J. Physical Chemistry, W. H. Freeman: New York, NY, 2002, Sections 21.2-4.