44 Ates¸ et al.
Arch. Pharm. Pharm. Med. Chem. 2003, 336, 39–46
CH3), 3.70 (s, 2 H, O=C-CH2), 4.08 (q, J = 7.1 Hz, 2 H, CH2O),
4.42 (s, 2 H, CH2-S), 7.03 (s, 1 H, 5-H thiazole), 7.87 (d, J =
5.9 Hz, 2 H, 3-H/5-H pyridine), 8.80 (d, J = 5.9 Hz, 2 H, 2-H/6-H
pyridine), 12.64 (s, 3 H, NH). – EI/MS [m/z (rel. int. %)]: M+ peak
was not observed. 421 (M–H2O)+ (3), 405 (M–H2S)+ (4), 360
(3), 331 (6), 259 (2), 228 (9), 213 (30), 186 (45), 179 (42), 155
(7), 106 (39), 72 (4), 71 (13), 62 (100).
(q, J = 7.1 Hz, 6 H, CH2O and 2-H/6-H morpholine), 4.36 (s, 2 H,
CH2-S), 6.97 (s, 1 H, 5-H thiazole), 12.32 (s, 1 H, NH). – EI/MS
[m/z (rel.int.%)]:391 (M + 2)+ (1), 389 (M+) (8), 344 (3), 316 (4),
259 (70), 228 (9), 213 (13), 204 (100), 186 (27), 162 (10), 130
(62), 114 (5), 113 (12), 86 (36), 72 (3).
Spectral data of 3 f: UV [λmax, nm, EtOH]: 273. – IR [ν, cm–1,
KBr]:1732 (C=O, ester), 1698 (C=O, amide), 1152 (C=S).– 1H-
NMR [400 MHz, δ ppm, DMSO-d6]: 1.19 (t, J = 7.1 Hz, 3 H,
CH3), 1.61–1.67 (m, 6 H, 3-H/4-H/5-H piperidine), 3.69 (s, 2 H,
O=C-CH2), 3.93 ( br. s, 2 H, 2-H piperidine), 4.10 (q, J = 7.1 Hz,
2 H, CH2O), 4.19 (br. s, 2 H, 6-H piperidine), 4.33 (s, 2 H, CH2-
S), 6.97 (s, 1 H, 5-H thiazole), 12.38 (s, 1 H, NH). – EI/MS [m/z
(rel.int. %)]: 388 (M + 1)+ (29), 387 (M+) (25), 259 (10), 228
(13), 213 (3), 202 (82), 186 (14), 160 (11), 128 (88), 112(18), 84
(76), 72 (51), 69 (100).
Spectral data of 3 m: UV [λmax, nm, EtOH]: 272. – IR [ν, cm–1,
KBr]:1728 (C=O, ester), 1629 (C=O, amide), 1206 (C=S).– 1H-
NMR [200 MHz, δ ppm, DMSO-d6]: 0.99–1.26 (m, 9 H, C-CH3),
1.52 (d, J = 7.3 Hz, 3 H, CH-CH3), 2.91 (q, J = 7.2 Hz, 2 H,
N-CH2), 3.67 (s, 2 H, O=C-CH2), 3.91 (q, J = 7.7 Hz, 2 H, N-
CH2), 4.07 (q, J = 7.1 Hz, 2 H, CH2O), 4.71 (q, J = 7.3 Hz, 1 H,
CH-S), 6.98 (s, 1 H, 5-H thiazole), 8.78 (s, 1 H, NH) (D2O ex-
change). – EI/MS [m/z (rel. int. %)]: 391 (M + 2)+ (4), 389 (M+)
(4), 344 (3), 316 (3), 273 (77), 242 (8), 213 (13), 204 (100), 186
(51), 148 (15), 116 (66), 114 (20), 72 (27).
Spectral data of 3 g: UV [λmax, nm, EtOH]: 272. – IR [ν, cm–1,
KBr]:1732 (C=O, ester), 1629 (C=O, amide), 1267 (C=S).– 1H-
NMR [200 MHz, δ ppm, DMSO-d6]:1.17 (t, J = 7.0 Hz, 3 H, CH3-
CH2O), 1.20 (t, J = 7.4 Hz, 3 H, C2-CH3 piperidine), 1.53–1.77
(m, 6 H, 3-H/4-H/5-H piperidine), 3.67 (s, 2 H, O=C-CH2),
3.56–3.96 (m, 3 H, 2-H/6-H piperidine), 4.07 (q, J = 7.1 Hz, 2 H,
CH2O), 4.31 (s, 2 H, CH2-S), 6.96 (s, 1 H, 5-H thiazole), 12.36
(s, 1 H, NH). – EI/MS [m/z (rel.int. %)]: 403 (M + 2)+ (1), 401
(M+) (3), 356 (3), 328 (3), 259 (23), 228 (86), 216 (100), 213
(17), 187 (10), 186 (77), 174 (21), 142 (73), 114 (18), 113(7), 98
(82), 83 (21), 72(4).
Spectral data of 3 n: UV [λmax, nm, EtOH]: 245, 269. – IR [ν,
cm–1, KBr]:1733 (C=O, ester), 1687 (C=O, amide), 1154 (C=S).
Spectral data of 3 o: UV [λmax, nm, EtOH]: 245, 274. – IR [ν,
cm–1, KBr]:1712 (C=O, ester), 1697 (C=O, amide), 1231 (C=S).
– 1H-NMR [400 MHz, δ ppm, DMSO-d6]:1.17 (t, J = 7.1 Hz, 6 H,
N(CH2CH3)2), 1.23 (t, J = 7.0 Hz, 3 H, CH3CH2O), 3.66 (s, 2 H,
O=C-CH2), 3.72–3.75 (m, 2 H, N-CH2), 3.89–3.94 (m, 2 H, N-
CH2), 4.07 (q, J = 7.1 Hz, 2 H, CH2O), 5.87 (s, 1 H, CH-S), 6.98
(s, 1 H, 5-H thiazole), 7.47 (d, J = 6.8 Hz, 2 H, 2-H/6-H phenyl),
7.35–7.41 (m, 3 H, 3-H/4-H/5-H phenyl), 12.67 (s, 1 H, NH). –
EI/MS [m/z (rel. int. %)]: 453 (M + 2)+ (1), 451 (M+) (1), 406 (6),
378 (19), 335 (100), 304 (18), 213 (14), 186 (46), 148 (58), 116
(85), 113(15), 91 (32), 72 (36).
Spectral data of 3 h: UV [λmax, nm, EtOH]: 272. – IR [ν, cm–1,
KBr]:1732 (C=O, ester), 1666 (C=O, amide), 1151 (C=S).– 1H-
NMR [200 MHz, δ ppm, DMSO-d6]: 0.91 (d, J = 6.1 Hz, 3 H, C4-
CH3 piperidine), 1.17 (t, J = 7.2 Hz, 3 H, CH3), 1.72–1.77 (m,
5 H, 3-H/4-H/5-H piperidine), 3.54–4.43 (m, 3 H, 2-H and C6-
Hax piperidine), 3.67 (s, 2 H, O=C-CH2), 4.10 (q, J = 7.1 Hz, 2 H,
CH2O), 4.30 (s, 2 H, CH2-S), 5.14 (br. s, 1 H, C6-Heq piperidine),
6.95 (s, 1 H, 5-H thiazole), 12.36 (s, 1 H, NH). – EI/MS [m/z (rel.
int. %)]: 403 (M + 2)+ (2), 401 (M+) (12), 328 (6), 259 (56), 228
(51), 216 (100), 213 (20), 188 (21), 186 (51), 174 (23), 142 (76),
114 (15), 98 (46), 83 (26), 72 (26).
Spectral data of 3 p: UV [λmax, nm, EtOH]: 251. – IR [ν, cm–1,
KBr]: 1731 (C=O, ester), 1685 (C=O, amide), 1247 (C=S).
Spectral data of 3 q: UV [λmax, nm, EtOH]: 244, 272. – IR [ν,
1
cm–1, KBr]: 1706 (C=O, ester and amide), 1157 (C=S). – H-
NMR [200 MHz, δ ppm, DMSO-d6]: 1.16 (t, J = 7.1 Hz, 3 H,
CH3), 1.87–2.06 (m, 4 H, 3-H/4-H pyrrolidine), 3.57–3.76 (m,
4 H, 2-H/5-H pyrrolidine), 3.65 (s, 2 H, O=C-CH2), 4.06 (q, J =
7.1 Hz, 2 H, CH2O), 5.91 (s, 1 H, CH-S), 6.97 (s, 1 H, 5-H thia-
zole), 7.35–7.44 (m, 5 H, phenyl), 12.65 (s, 1 H, NH). – EI/MS
[m/z (rel. int. %)]: 451 (M + 2)+ (3), 449 (M+) (11), 404 (10), 376
(7), 335 (75), 304 (20), 213 (38), 186 (46), 146 (50), 114 (100),
91 (4), 72 (48).
Spectral data of 3 i: UV [λmax, nm, EtOH]: 272. – IR [ν, cm–1,
KBr]: 1734 (C=O, ester), 1685 (C=O, amide), 1152 (C=S).
Spectral data of 3 j: UV [λmax, nm, EtOH]: 251. – IR [ν, cm–1,
KBr]:1732 (C=O, ester), 1661 (C=O, amide), 1213 (C=S).– 1H-
NMR [200 MHz, δ ppm, DMSO-d6]: 1.00–1.35 (m, 3 H, CH3-
CH2-O), 1.20 (d, J = 6.44 Hz, 6 H, C2-CH3 and C6-CH3 piperid-
ine), 1.68–1.78 (m, 6 H, 3-H/4-H/5-H piperidine), 3.67 (s, 2 H,
O=C-CH2), 4.07 (q, J = 7.0 Hz, 2 H, CH2O), 4.30 (s, 2 H, CH2-S),
4.83–4.91 (m, 1 H, 2-H piperidine), 5.37–5.50 (m, 1 H, 6-H pip-
eridine), 6.96 (s, 1 H, 5-H thiazole), 8.72 (s, 1 H, NH) (D2O
exchange).– EI/MS [m/z (rel.int.%)]:417(M + 2)+ (1), 415 (M+)
(1), 342 (3), 259 (4), 230 (54), 228 (100), 213 (20),188 (27), 186
(80), 156 (27), 112 (78), 97 (18), 84 (2),72(4).
Spectral data of 3 r: UV [λmax, nm, EtOH]: 246. – IR [ν, cm–1,
KBr]:1732 (C=O, ester), 1629 (C=O, amide), 1230 (C=S).– 1H-
NMR [200 MHz, δ ppm, DMSO-d6]: 1.14, 1.18 (dt, J = 7.5 Hz,
3 H, CH3), 3.41–4.08 (m, 12 H, O=C-CH2, 2-H/3-H/5-H/6-H
morpholine, CH2O), 5.87, 5.92 (ds, 1 H, CH-S), 6.81, 6.97 (ds,
1 H, 5-H thiazole), 7.32–7.92 (m, 5 H, phenyl), 9.18, 9.21 (ds,
1 H, NH). – EI/MS [m/z (rel. int. %)]: 391 (M + 2)+ (1), 389 (M+)
(4), 344 (3), 316 (3), 273 (77), 242 (8), 213 (13), 204 (100), 186
(51), 148 (15), 116 (66), 114 (20), 72 (27).
Spectral data of 3 k: UV [λmax, nm, EtOH]: 252, 273. – IR [ν,
cm–1, KBr]:1734 (C=O, ester), 1686 (C=O, amide), 1149 (C=S).
– 1H-NMR [200 MHz, δ ppm, DMSO-d6]:1.18 (t, J = 7.1 Hz, 3 H,
C-CH3), 2.21 (s, 3 H, N-CH3), 2.39–2.43 (m, 4 H, 3-H/5-H piper-
azine), 3.68 (s, 2 H, O=C-CH2), 3.81–4.23 (m, 4 H, 2-H/6-H pip-
erazine), 4.08 (q, J = 7.1 Hz, 2 H, CH2O), 4.33 (s, 2 H, CH2-S),
6.97 (s, 1 H, 5-H thiazole), 12.38 (s, 1 H, NH). – EI/MS [m/z (rel.
int. %)]: 404 (M + 2)+ (1), 402 (M+) (2), 357 (7), 329 (6), 259
(32), 228 (95), 217 (100), 213 (31), 187 (10), 186 (38), 175 (82),
143 (91), 114 (6), 113 (9), 99 (28), 83 (29), 72 (3).
Spectral data of 3 s: UV [λmax, nm, EtOH]: 246, 275. – IR [ν,
cm–1, KBr]:1714 (C=O, ester), 1690 (C=O, amide), 1228 (C=S).
– 1H-NMR [200 MHz, δ ppm, DMSO-d6]:1.16 (t, J = 7.2 Hz, 3 H,
CH3), 1.60 (br. s, 6 H, 3-H/4-H/5-H piperidine), 3.65 (s,
2 H,O=C-CH2), 3.89 (br.s, 3 H, 2-H and C6-Hax. piperidine), 4.05
(q, J = 7.1 Hz, 2 H, CH2O), 4.37 (br. s, 1 H, C6-Heq. piperidine),
5.84 (s, 1 H, CH-S), 6.98 (s, 1 H, 5-H thiazole), 7.30–7.43 (m,
5 H, phenyl), 12.69 (s, 1 H, NH). – EI/MS [m/z (rel. int. %)]: 464
(M + 1)+ (1), 463 (M+) (3), 418 (4), 390 (1), 335 (100), 304 (20),
278 (60), 213 (15), 186 (58), 160 (43), 128 (78), 113 (20), 91
(45), 84 (41), 72 (24), 69 (51).
Spectral data of 3 l:UV [λmax, nm, EtOH]:272, 337.– IR [ν, cm–1,
KBr]:1730 (C=O, ester), 1655 (C=O, amide), 1172 (C=S).– 1H-
NMR [200 MHz, δ ppm, DMSO-d6]: 1.18 (t, J = 7.1 Hz, 3 H,