A Novel Lead for Specific Anti-HIV-1 Agents: L-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thy-mine

Journal of Medicinal Chemistry

Volumn 32, Issue 12, 1989, Pages 2507-2509

  Miyasaka, Tadashi ^a   Tanaka, Hiromichi ^a   Hayakawa, Hiroyuki ^a   Clercq, Erik De ^b   Walker, Richard T ^c   Balzarini, Jan ^b   Baba, Masanori ^b  

^a SHOWA UNIVERSITY   (Japan)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1 [(2 HYDROXYETHOXY)METHYL] 6 PHENYLTHIOTHYMINE; 2',3' DIDEOXYADENOSINE; ACYCLOURIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG; ZALCITABINE; ZIDOVUDINE;

ANIMAL CELL; CELL CULTURE; CELL STRAIN MT 4; CRYSTALLOGRAPHY; CYTOTOXICITY; DRUG METABOLISM; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS; LETTER; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; VIRUS INFECTION;

ANIMAL; ANTIVIRAL AGENTS; CELL SURVIVAL; CELLS, CULTURED; CHEMISTRY; HIV-1; HIV-2; MICE; MOLECULAR CONFORMATION; REVERSE TRANSCRIPTASE INHIBITORS; THYMINE; VIRUS REPLICATION;

EID: 0024408374     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00132a002     Document Type: Letter

References (40)

1. Yarchoan, R.; Weinhold, K. J.; Lyerly, H. K.; Gelmann, E.; Blum, R. M.; Shearer, G. M.; Mitsuya, H.; Collins, J. M.; Myers, C. E.; Klecker, R. W.; Markham, P. D.; Durack, D. T.; Lehrman, S. N.; Barry, D. W.; Fischl, M. A.; Gallo, R. C.; Bolognesi, D. P.; Broder, S. Lancet 1986, 1, 575–580.
2. Fischl, M. A.; Richman, D. D.; Grieco, M. H.; Gottieb, 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.; the AZT Collaborative Working Group N. Engl. J. Med. 1987,317, 185–191.
3. De Clercq, E. J. Med. Chem. 1986. 29. 1561–1569.
4. Mitsuya, H.; Broder, S. Proc. Natl. Acad. Sci. U. S. A. 1986, 83, 1911–1915.
5. Herdewijn, P.; Pauwels, R.; Baba, M.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1987, 30, 2131–2137.
6. Marquez, V. E.; Tseng, C. K. H.; Kelley, J. A.; Mitsuya, H.; Broder, S.; Roth, J. S.; Driscoll, J. S. Biochem. Pharmacol. 1987, 36, 2719–2722.
7. Herdewijn, P.; Balzarini, J.; Baba, M.; Pauwels, R.; Van Aerschot, A.; Janssen, G.; De Clercq, E. J. Med. Chem. 1988, 31, 2040–2048.
8. Pauwels, R.; Baba, M.; Balzarini, J.; Herdewijn, P.; Desmyter, J.; Robins, M. J.; Zou, R.; Madej, D.; De Clercq, E. Biochem. Pharmacol. 1988, 37, 1317–1325.
9. Balzarini, J.; Baba, M.; Pauwels, R.; Herdewijn, P.; De Clercq, E. Biochem. Pharmacol. 1988, 37, 2847–2856.
10. Chu, C. K.; Schinazi, R. F.; Arnold, B. H.; Cannon, D. L.; Doboszewski, B.; Bhadti, V. B.; Gu, Z. Biochem. Pharmacol. 1988, 37, 3543–3548.
11. Schreiber, S.; Ikemoto, N. Tetrahedron Lett. 1988, 29, 3211–3214.
12. Bazin, H.; Chattopadhyaya, J.; Datema, R.; Ericson, A. C.; Gilljam, G.; Johansson, N. G.; Hansen, J.; Koshida, R.; Moelling, K.; Oberg, B.; Remaud, G.; Stening, G.; Vrang, L.; Wahren, B.; Wu, J. C. Biochem. Pharmacol. 1989 38 109–119
13. Lin, T. S.; Chen, M. S.; McLaren, C.; Gao, Y. S.; Ghazzouli, I.; Prusoff, W. H. J. Med. Chem. 1987, 30, 440–444.
14. Kim, C. H.; Marquez, V. E.; Broder, S.; Mitsuya, H.; Driscoll, J. S. J. Med. Chem. 1987, 30, 862–866.
15. Herdewijn, P.; Balzarini, J.; De Clercq, E.; Pauwels, R.; Baba, M.; Broder, S.; Vanderhaeghe, H. J. Med. Chem. 1987, 30, 1270–1278.
16. Lin, T. S. ; Guo, J. Y. ; Schinazi, R. F.; Chu, C. K.; Xiang, J. N. ; Prusoff, W. J. Med. Chem. 1988, 31, 336–340.
17. Balzarini, J.; Van Aerschot, A.; Herdewijn, P.; De Clercq, E. Biochem. Pharmacol. 1989, 38, 869–874.
18. Hayashi, S.; Phadtare, S.; Zemlicka, J.; Matsukura, M.; Mitsuya, H.; Broder, S. Proc. Natl. Acad. Sci. U. S. A. 1988, 85, 6127–6131.
19. Pauwels, R.; Balzarini, J.; Schols, D.; Baba, M.; Desmyter, J.; Rosenberg, I.; Holy, A.; De Clercq, E. Antimicrob. Agents Chemother. 1988, 32, 1025–1030.
20. Balzarini, J.; Naesens, L.; Herdewijn, P.; Rosenberg, I.; Holy, A.; Pauwels, R.; Baba, M.; Johns, D. G.; De Clercq, E. Proc. Natl. Acad. Sci. U. S. A. 1989, 86, 332–336.
21. Tanaka, H.; Hayakawa, H.; Miyasaka, T. Tetrahedron 1982, 38, 2635–2642.
22. Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787–790.
23. Tanaka, H.; Matsuda, A.; Iijima, S.; Hayakawa, H.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 2164–2167.
24. Tanaka, H.; Hayakawa, H.; Iijima, S.; Haraguchi, K.; Miyasaka, T. Tetrahedron 1985, 41, 861–866.
25. Hayakawa, H.; Tanaka, H.; Miyasaka, T. Tetrahedron 1985, 41, 1675–1683.
26. Tanaka, H.; Hirayama, M.; Suzuki, M.; Miyasaka, T.; Matsuda, A.; Ueda, T. Tetrahedron 1986,42, 1971–1980.
27. Tanaka, H.; Hayakawa, H.; Obi, K.; Miyasaka, T. Tetrahedron 1986, 42, 4187–4195.
28. Hayakawa, H.; Tanaka, H.; Obi, K.; Itoh, M.; Miyasaka, T. Tetrahedron Lett. 1987, 28, 87–90.
29. Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72–79.
30. Suzuki, M.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 4056–4063.
31. Hayakawa, H.; Tanaka, H.; Haraguchi, K.; Mayumi, M.; Nakajima, M.; Sakamaki, T.; Miyasaka, T. Nucleosides Nucleotides 1988, 7, 121–128.
32. Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189–191.
33. Tanaka, H.; Iijima, S.; Matsuda, A.; Hayakawa, H.; Miyasaka, T.: Ueda. T. Chem. Pharm. Bull. 1983. 31. 1222–1227.
34. Tanaka, H.; Hayakawa, H.; Haraguchi, K.; Miyasaka, T. Nucleosides Nucleotides 1985, 4, 607–612.
35. Rosowsky, A.; Kim, S. H. ; Wick, M. J. Med. Chem. 1981, 24, 1177–1181.
36. Pauwels, R.; De Clercq, E.; Desmyter, J.; Balzarini, J.; Goubau, P.; Herdewijn, P.; Vanderhaeghe, H.; Vandeputte, M. J. Virol. Methods 1987, 16, 171–185.
37. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. J. Virol. Methods 1988. 20. 309–322.
38. The triphosphate of 5e was synthesized and characterized according to published methods: Hoard, D. E.; Ott, D. G. J. Am. Chem. Soc. 1965, 87, 1785–1788. Yoshikawa, M.; Kato, T.; Takenishi, T. Bull. Chem. Soc. Jpn. 1969, 42, 3505–3508.
39. HIV-1 reverse transcriptase was prepared and assayed according to published methods: Balzarini, J.; Herdewijn, P.; Pauwels, R.; Broder, S.; De Clercq, E. Biochem. Pharmacol. 1988, 37, 2395–2403.
40. Baba, M.; Pauwels, R.; Balzarini, J.; Desmyter, J.; De Clercq, E. Proc. Natl. Acad. Sci. U. S. A. 1988, 85, 6132–6136.