I.O. Donkor et al. / European Journal of Medicinal Chemistry 38 (2003) 605Á
/
611
611
1
cmꢂ1; H-NMR (CDCl3) d 2.03 (s, 3H), 3.14 (t, 2H),
MeOH); IR (NaCl) 3630, 3393, 1700, 1684, 1654, 1636
cmꢂ1; H-NMR (CDCl3) d 1.39Á
1.71 (m, 4H), 2.38 (s, 3H), 2.60Á2.74 (dt, 4H), 4.72 (bs,
2H), 5.18 (bs, 2H), 7.17Á7.28 (m, 5H). Anal.
/
1.45 (m, 2H), 1.61Á
/
1
3.37 (t, 2H), 4.69 (bs, 2H), 5.07 (bs, 2H), 7.20Á8.10 (7H).
Anal. (C19H18N4S) C, H, N, S.
/
/
/
5.1.6.3. 5-Methyl-6-(2-naphthalen-2-yl-ethyl)-
thieno[2,3-d]pyrimidine-2,4-diamine (4c). Compound
4c was obtained as an off-white solid in 77% yield.
(C18H22N4S) C, H, N, S.
M.p. 230Á
/
231 8C; Rf 0.6 (silica gel, 9:1 CHCl3ÁMeOH);
/
IR (KBr) 3159, 2722, 1649, 1562, 1526, 1444 cmꢂ1; 1H-
NMR (DMSO) d 2.18 (s, 3H), 2.99 (m, 4H), 6.04 (bs,
References
2H), 6.43 (bs, 2H), 7.30Á
(C19H18N4S) C, H, N, S.
/8.00 (m, 7H). Anal.
[1] H. Masur, J.E. Kaplan, K.K. Holmes, Ann. Intern. Med. 137
(2002) 435Á478.
[2] F.J. Palella, K.M. Delaney, A.C. Moorman, M.O. Loveless, J.
/
Fuhrer, G.A. Satten, D.J. Aschman, S.D Holmberg, N. Engl. J.
5.1.6.4. 5-Methyl-6-(3-phenyl-propyl)-thieno[2,3-
d]pyrimidine-2,4-diamine (4d). Compound 4d was ob-
Med. 338 (1998) 853Á860.
/
[3] M. Floridia, V. Fragola, C.M. Galluzzo, G. Giannini, M.F.
tained as a white solid in 75% yield. M.p. 136Á
/
138 8C;
Pirrilo, M. Andreotti, C. Tomino, S. Vella, HIV Med. 3 (2000)
Rf 0.6 (silica gel, 9:1 CHCl3ÁMeOH); IR (NaCl) 3453,
/
75Á84.
/
3321, 3120, 2929, 1617, 1560, 1522, 1438, 1292, 925, 786,
1
[4] D.M. Forrest, E. Seminari, R.S. Hogg, B. Yip, J. Raboud, L.
698 cmꢂ1; H-NMR (CDCl3) d 1.96 (p, 2H), 2.33 (s,
Lawson, P. Phillips, M.T. Schechter, M.V. O’Shaughnessy, J.S.
Montaner, Clin. Infect. Dis. 27 (1998) 1379Á
[5] A. Morris, R.M. Wachter, J. Luce, J. Turner, L. Huang, AIDS 17
(2003) 73Á80.
[6] R. Manfredi, F. Chiodo, Sex Transm. Infect. 76 (2000) 145Á
[7] R. Manfredi, L. Calza, F. Chiodo, Eur. J. Clin. Microbiol. Infect.
Dis. 20 (2001) 410Á413.
[8] S.A. Marques, A.M. Robles, A.M. Tortorano, M.A. Tuculet, R.
Negroni, R.P. Mendes, Med. Mycol. 38 (Suppl. 1) (2000) 269Á
279.
[9] M.E. Klepser, T.B. Klepser, Drugs 53 (1997) 40Á
[10] B.I. Schweitzer, A.P. Dicker, J.R. Bertino, FASEB J. 4 (1990)
2441Á2452.
/
1385.
3H), 2.65Á
/
2.76 (dt, 4H), 4.70 (bs, 2H), 5.16 (bs, 2H),
7.17Á7.31 (m, 5H). Anal. (C16H18N4S) C, H, N, S.
/
/
/
146.
5.1.6.5. 5-Methyl-6-(3-naphthalen-1-yl-propyl)-
thieno[2,3-d]pyrimidine-2,4-diamine (4e). Compound
4e was obtained as a yellow solid in 84% yield. M.p.
/
/
236 8C; Rf 0.5 (silica gel, 9:1 CHCl3Á
/MeOH); IR (KBr)
3170, 2924, 1611, 1562, 1524, 1439, 1319, 1284, 778
/73.
1
cmꢂ1; H-NMR (CDCl3) d 2.05Á
3H), 2.81Á2.86 (t, 2H), 3.11Á3.16 (t, 2H), 4.67 (bs, 2H),
5.12 (bs, 2H), 7.33Á8.10 (m, 7H). Anal. (C20H20N4S) C,
H, N, S.
/
2.15 (p, 2H), 2,34 (s,
/
/
/
[11] A. Rosowsky, C.E. Mota, J.E. Wright, J.H. Freisheim, J.J.
/
Heusner, J.J. McCormack, S.F. Queener, J. Med. Chem. 36
(1993) 3103Á
[12] A. Gangjee, X. Guo, S.F. Queener, V. Cody, N. Galitsky, J.R.
Luft, W. Pangborn, J. Med. Chem. 41 (1998) 1263Á1271.
[13] A. Gangjee, X. Guo, S.F. Queener, V. Cody, N. Galitsky, J.R.
Luft, W. Pangborn, J. Med. Chem. 41 (1998) 1263Á1271.
[14] S.F. Queener, J. Med. Chem. 38 (1995) 4739Á4759.
[15] A. Rosowsky, V. Cody, N. Galitsky, H. Fu, A.T. Papoulis, S.F.
Queener, J. Med. Chem. 42 (1999) 4853Á4860.
/
3112.
5.1.6.6. 5-Methyl-6-(3-naphthalen-2-yl-propyl)-
thieno[2,3-d]pyrimidine-2,4-diamine (4f). Compound 4f
was obtained as an off-white solid in 57% yield. M.p.
246 8C; Rf 0.5 (silica gel, 9:1 CHCl3Á
3135, 1654, 1636, 1617, 1560, 1541, 1522, 1507, 1457,
1437, 668 cmꢂ1 1H-NMR (CDCl3) d 2.00Á
2.10 (p,
2H), 2,33 (s, 3H), 2.75Á2.87 (t, 4H), 4.66 (bs, 2H), 5.12
(bs, 2H), 7.32Á7.82 (m, 7H). Anal. (C20H20N4S) C, H,
N, S.
/
/
/
/MeOH); IR (KBr)
/
;
/
[16] W.J. Suling, L.E. Seitz, V. Pathak, L. Westbrook, E.W. Barrow,
/
S. Zywno-Van-Ginkel, R.C. Reynolds, J.R. Piper, W.M. Barrow,
/
Antimicrob. Agents Chemother. 44 (2000) 2784Á2793.
/
[17] C.M. Shoen, O. Choromanska, R.C. Reynolds, J.R. Piper, C.A.
Johnson, M.H. Cynamon, Antimicrob. Agents Chemother. 42
(1998) 3315Á3316.
[18] J.R. Piper, C.A. Johnson, C.A. Krauth, R.L. Carter, C.A.
/
5.1.7. 5-Methyl-6-(4-phenyl-butyl)-thieno[2,3-
d]pyrimidine-2,4-diamine (4g)
Compound 4g was obtained as a yellow solid in 22%
Hosmer, S.F. Queener, S.E. Borotz, E.R. Pfefferkorn, J. Med.
Chem. 39 (1996) 1271Á1280.
/
[19] A. Rosowsky, C.E. Mota, J.E. Wright, J.H. Freisheim, J.J.
yield. M.p. 138 8C; Rf 0.5 (silica gel, 9:1 CHCl3Á
MeOH); IR (NaCl) 3480, 3456, 3290, 3143, 2940,
/
Heusner, J.J. McCormack, S.F. Queener, J. Med. Chem. 36
(1993) 3103Á
/
3112.
1654, 1616, 1563, 1523, 1471, 1435, 787, 731, 713
[20] A. Rosowsky, K.K. Chen, M. Lin, J. Med. Chem. 16 (1973) 191Á
/
cmꢂ1
(s, 3H), 2.63Á
7.17Á7.29 (m, 5H). Anal. (C18H22N4S) C, H, N, S.
;
1H-NMR (CDCl3) d 1.68Á
/1.76 (m, 4H), 2.38
194.
[21] E.F. Elslager, P. Jocob, L.M. Werbel, J. Heterocyclic Chem. 9
/
2.77 (dt, 4H), 4.72 (bs, 2H), 5.18 (bs, 2H),
(1972) 775Á
[22] S.F. Queener, M.S. Bartlett, M.A. Jay, M.M. Durkin, J.W. Smith,
Antimicrob. Agents Chemother. 31 (1987) 1323Á1327.
[23] M.C. Broughton, S.F. Queener, Antimicrob. Agents Chemother.
35 (1991) 1348Á1355.
[24] L.-C. Chio, S.F. Queener, Antimicrob. Agents Chemother. 37
(1993) 1914Á1923.
/
782.
/
/
5.1.8. 5-Methyl-6-(5-phenyl-pentyl)-thieno[2,3-
d]pyrimidine-2,4-diamine (4h)
Compound 4h was obtained as a white solid in 10%
/
yield. M.p. 140 8C; Rf 0.5 (silica gel, 9:1 CHCl3Á
/
/