R. Costi et al. / Bioorg. Med. Chem. Lett. 14 (2004) 1745–1749
1749
References and notes
16. Marchand, C.; Zhang, X.; Pais, G. C. G.; Cowansage, K.;
Neamati, N.; Burke, T. R., Jr.; Pommier, Y. J. Biol.
Chem. 2002, 277, 12596.
1
2
. De Clercq, E. J. Med. Chem. 1995, 38, 2491.
. Vacca, J. P.; Condra, J. H. Drugs Discovery Today 1997,
17. Pais, G. C. G.; Zhang, X.; Marchand, C.; Neamati, N.;
Cowansage, K.; Svarovskaia, E. S.; Pathak, V. K.; Tang,
Y.; Nicklaus, M.; Pommier, Y.; Burke, T. R., Jr. J. Med.
Chem. 2002, 45, 3184.
18. Kawasuji, T.; Yoshinaga, T. Patent WO 01 17,968; Chem.
Abstr. 2001, 134, 237486m.
2, 261.
3
4
. Brettle, R. P.; Wilson, A.; Povey, S.; Morris, S.; Morgan,
R.; Leen, C. L.; Hutchinson, S.; Lewis, S.; Gore, S. Int. J.
STD AIDS 1998, 9, 80.
. Mocroft, A.; Vella, S.; Benfield, T. L.; Chiesi, A.; Miller,
V.; Gargalianos, P.; d’Arminio-Monforte, A.; Yust, I.;
Bruun, J. N.; Philips, A. N.; Lundgren, J. D. Lancet 1998,
19. Barreca, M. L.; Lee, K. W.; Chimirri, A.; Briggs, J. M.
Biophys. J. 2003, 84, 1450.
20. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J.; Meyer,
E. E., Jr.; Brice, M. D.; Rodgers, J. R.; Kennard, O.;
Shimanouchi, T.; Tasumi, M. J. Mol. Biol. 1977, 112, 535.
21. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J.; Meyer,
E. F., Jr.; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shi-
manouchi, T.; Tasumi, M. Eur. J. Biochem. 1977, 80, 319.
22. To check for methodology correctness the same con-
formational search was also carried out on 5CITEP (7).
The global minimum found showed an atomic roots
means square distance on all heavy atoms of only 0.36.
23. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Lis-
kamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hen-
drickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
24. The complex IN/5CITEP was also submitted to the same
minimization procedure for direct comparisons.
352, 1725.
5
6
7
. Neamati, N.; Sunder, S.; Pommier, Y. Drugs Discovery
Today 1997, 2, 487.
. Sotriffer, C. A.; Ni, H.; McCammon, J. A. J. Med. Chem.
2000, 43, 4109.
. Hazuda, D. J.; Felock, P.; Witmer, M.; Wolfe, A.; Still-
mock, K.; Grobler, J. A.; Espeseth, A.; Gabryelski, L.;
Schleif, W.; Blau, C.; Miller, M. D. Science 2000, 287,
646.
8
. Stanwell, C.; Ye, B.; Yuspa, S. H.; Burke, T. R., Jr. Bio-
chem. Pharmacol. 1996, 52, 475.
9
. Goldgur, Y.; Craigie, R.; Cohen, G. H.; Fujiwara, T.;
Yoshinaga, T.; Fujishita, T.; Sugimoto, H.; Endo, T.;
Murai, H.; Davies, D. R. Proc. Natl. Acad. Sci. U.S.A.
1
999, 96, 13040.
25. Oprea, T. I.; Waller, C. L.; Marshall, G. R. Drug Des.
Discovery 1994, 12, 2 9.
1
0. Lin, Z.; Neamati, N.; Zhao, H.; Kiryu, Y.; Turpin, J. A.;
Aberham, C.; Strebel, K.; Kohn, K.; Witvrouw, M.; Pan-
necouque, C.; Debyser, Z.; De Clercq, E.; Rice, W. G.;
Pommier, Y.; Burke, T. R., Jr. J. Med. Chem. 1999, 42,
26. Carlson, H. A.; Masukawa, K. M.; Rubins, K.; Bushman,
F. D.; Jorgensen, W. L.; Lins, R. D.; Briggs, J. M.;
McCammon, J. A. J. Med. Chem. 2000, 43, 2100.
27. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols,
D.; Herdewijn, P.; Desmyster, J.; De Clercq, E. J. Virol.
Methods 1988, 20, 309.
28. Artico, M.; Di Santo, R.; Costi, R.; Novellino, E.; Greco,
G.; Massa, S.; Tramontano, E.; Marongiu, M. E.; De
Montis, A.; La Colla, P. J. Med. Chem. 1998, 41, 3948.
29. Tramontano, E.; La Colla, P.; Cheng, Y.-C. Biochemistry
1998, 37, 7237.
1401.
1
1
1. McDougall, B.; King, P. J.; Wu, B. W.; Hostomsky, Z.;
Reinecke, M. G.; Robinson, W. E., Jr. Antimicrob. Agents
Chemother. 1998, 42, 140.
2. Pluymers, W.; Neamati, N.; Pannecouque, C.; Fikkert,
V.; Marchand, C.; Burke, T. R., Jr.; Pommier, Y.; Schols,
D.; De Clercq, E.; Debyser, Z.; Witvrouw, M. Mol.
Pharmacol. 2000, 58, 641.
1
1
1
3. Mekouar, K.; Mouscardet, J.-F.; Desmae
Leh, H.; Savoure, D.; Auclair, C.; d’Angelo, J. J. Med.
Chem. 1998, 41, 2846.
4. Zouhiri, F.; Mouscardet, J.-F.; Mekouar, K.; Desmae
D.; Savoure, D.; Leh, H.; Subra, F.; Le Bret, M.; Auclair,
C.; d’Angelo, J. J. Med. Chem. 2000, 43, 1533.
5. Wai, J. S.; Egbertson, M. S.; Payne, L. S.; Fisher, T. E.;
Embrey, M. W.; Tran, L. O.; Melamed, J. Y.; Langford,
H. M.; Guare, J. P.; Zhuang, L.; Grey, V. E.; Vacca, J. P.;
Holloway, M. K.; Naylor-Olsen, A. M.; Hazuda, D. J.;
Felock, P. J.; Wolfe, A. L.; Stillmock, K. A.; Schleif,
W. A.; Gabryelski, L. J.; Young, S. D. J. Med. Chem.
¨
le, D.; Subra, F.;
30. All new compounds exhibited satisfactory spectroscopic
and analytical properties. Data for compound 8a, includ-
ing chemical and physical data, are reported: yield 68%,
´
ꢁ
ꢀ1
3400
¨
le,
mp 146–148 C (from toluene). IR (nujol): cm
(OH), 1700 (CO acid) and 1590 (CO); 1H NMR
(200 MHz, DMSO-d ): d 5.43 (s, 2H, CH ), 6,30 (m, 1H,
pyrrole C4-H), 6.45 (s, 1H, C3-H), 6.69 (d, 1H, J =15.4
Hz, C5-H), 7.01–7.40 (m, 7H, pyrrole C3-H and C5-H
and benzene H), 7.65 (d, 1H, J =15.4 Hz, C6-H), 15.50
(bs, 2H, OH). Anal. calcd for C17 (297.31): C,
´
6
2
t
t
H15NO
4
68.68; H, 5.09; 4.71. Found: 68.63; 5.18; 4.74. Data for
compounds 8b–f and 11a–f are reported in the Supple-
mentary Information section.
2000, 43, 4923.