Med Chem Res
2-(3-(4-(Benzo[d]thiazol-2-yl)piperazin-1-yl)propylthio)-
5-p-tolyl-1,3,4-oxadiazole (8m)
3.65–3.78 (m, 4H), 7.04–7.12 (m, 1H), 7.36–7.42 (m, 2H),
7.46–7.63 (m, 3H), 7.94–8.10 (m, 2H). 13C NMR (CDCl3)
d = 25.4 (CH2), 28.1 (CH2), 47.5 (CH2), 52.7 (CH2), 55.8
(CH2), 117.2 (CH), 120.6 (CH), 121.3 (CH), 125.9 (CH),
126.1 (CH), 126.5 (CH), 132.5 (CH), 150.6 (C), 165.4 (C),
164.1 (C), 167.9 (C). HRMS: cal. for C22H23N5O2S
422.1635 found 422.16378.
Mp: 159–161 °C; 1H NMR (200 MHz, CDCl3) d: 2.05–2.13
(m, 2H), 2.42 (s, 3H), 2.56–2.65 (m, 6H), 3.38 (t, 2H,
J = 7.2 Hz), 3.63–3.70 (m, 4H), 7.07 (t, 1H, J = 7.6 Hz),
7.27–7.32 (m, 3H, J = 7.5 Hz), 7.55 (d, 1H, J = 8.6 Hz),
7.59 (d, 1H, J = 7.6 Hz), 7.88 (s, 1H), 7.90 (s, 1H). 13C
NMR (CDCl3) d = 21.6 (CH2), 26.3 (CH2), 30.4 (CH2), 48.2
(2CH2), 52.3 (2CH2), 56.4 (CH2), 119.0 (CH), 120.6 (CH),
121.3 (CH), 125.9 (CH), 126.5 (CH), 129.7 (CH), 130.7
(CH), 142.1 (C), 152.6 (C), 164.0 (C), 165.8 (C), 168.7 (C).
HRMS: cal. for C23H25N5OS2 451.15502, found 451.1496.
2-(5-(3-(4-(Benzo[d]oxazol-2-yl)piperazin-1-yl)
propylthio)-1,3,4-oxadiazol-2-yl)-N-phenylacetamide (8j)
Mp: 175–177 °C; 1H NMR (200 MHz, CDCl3) d:1.95–
2.08 (m, 2H), 2.48–2.61 (m, 6H), 3.70 (t, 2H, J = 5.3 Hz),
3.65–3.74 (m, 4H), 4.85 (d, 2H, J = 6.0 Hz), 7.02 (t, 1H,
J = 7.5 Hz), 7.16 (t, 1H, J = 7.4 Hz), 7.23–7.30 (m, 2H),
7.35 (d, 1H, J = 7.5 Hz), 7.39–7.48 (m, 2H), 7.49–7.56
(m, 1H), 7.81–7.89 (m, 2H). 13C NMR (CDCl3) d = 25.8
(CH2), 29.5 (CH2), 30.2 (CH2), 34.6 (CH2), 48.2 (2CH2),
51.9 (2CH2), 56.2 (CH2), 108.6 (CH), 115.9 (CH), 120.6
(CH), 123.8 (2CH), 127.2 (2CH), 128.4 (CH), 131.8 (CH),
132.9 (CH), 142.6 (C), 148.4 (C), 161.8 (C), 164.7 (C),
165.2 (C), 168.5 (C=O). HRMS: cal. for C24H26N6O3S
478.17865 found 478.17859.
2-(3-(4-(Benzo[d]thiazol-2-yl)piperazin-1-yl)propylthio)-
5-(4-chlorophenyl)-1,3,4-oxadiazole (8n)
1
Mp: 155–157 °C; H NMR (200 MHz, CDCl3) d: 2.03–
2.13 (q, 2H), 2.54–2.69 (m, 6H), 3.40 (t, 2H, J = 6.7 Hz),
3.62–3.71 (m, 4H), 7.05–7.12 (m, 1H), 7.27–7.34 (m, 1H),
7.47 (s, 1H), 7.50 (s, 1H), 7.60 (d, 1H, J = 7.5 Hz), 7.93 (s,
1H) 7.96 (s, 1H).13C NMR (CDCl3) d = 25.9 (CH2), 30.1
(CH2), 47.2 (CH2), 55.3 (CH2), 56.5 (CH2), 108.7 (CH),
116.5 (CH), 116.2 (CH), 119.0 (CH), 120.6 (CH), 121.4
(CH), 126.0 (CH), 128.8 (CH), 128.9 (CH), 130.7 (CH),
152.7 (C), 164.5 (C), 166.3 (C), 168.7 (C). HRMS: cal. for
C22H22ClN5OS2 472.10076, found 472.10065.
2-(3-(4-(Benzo[d]thiazol-2-yl)piperazin-1-yl)propylthio)-
5-(4-methoxyphenyl)-1,3,4-oxadiazole (8k)
1
Mp: 131–134 °C; H NMR (400 MHz, CDCl3) d: 2.04–
2-(3-(4-(Benzo[d]thiazol-2-yl)piperazin-1-yl)propylthio)-
5-(4-fluorophenyl)-1,3,4-oxadiazole (8o)
2.12 (q, 2H), 2.54–2.64 (m, 6H), 3.37 (t, 2H,
J = 6.7 Hz), 3.63–3.69 (m, 4H), 3.87 (s, 3H), 6.98–7.00
(m, 2H) 7.07 (t, 1H, J = 7.7 Hz), 7.29 (t, 1H, J =
7.7 Hz), 7.55 (d, 1H, J = 7.7 Hz), 7.60 (d, 1H, J =
7.7 Hz), 7.93 (s, 1H), 7.95 (s, 1H). 13C NMR (CDCl3)
d = 26.2 (CH2), 30.4 (CH2), 48.2 (CH2), 52.2 (CH2), 55.3
(CH2), 56.4 (CH2), 114.4 (CH), 116.1 (CH), 119.0 (CH),
120.6 (CH), 121.3 (CH), 125.3 (CH), 125.9 (CH), 128.3
(CH), 130.6 (CH), 162.1 (C), 163.6 (C), 165.6 (C), 168.6
(C). HRMS: cal. for C23H25N5O2S2 468.15224, found
468.15182.
1
Mp: 133–135 °C; H NMR (300 MHz, CDCl3) d: 2.06–
2.16 (q, 2H), 2.54–2.64 (m, 6H), 3.39 (t, 2H, J = 7.2 Hz),
3.62–3.69 (m, 4H), 6.99–7.07 (m, 1H), 7.14–7.30 (m, 3H),
7.60 (d, 1H, J = 8.3 Hz), 7.55 (d, 1H, J = 8.3 Hz),
7.98–8.06 (m, 2H). 13C NMR (CDCl3) d = 26.3 (CH2),
30.4 (CH2), 48.3 (CH2), 52.3 (CH2), 56.4 (CH2), 116.2
(CH), 116.5 (CH), 119.0 (CH), 120.6 (CH), 121.4 (CH),
125.9 (CH), 128.8 (CH), 128.9 (CH), 130.7 (CH), 152.7
(C), 164.5 (C), 164.8 (C), 166.3 (C), 168.7 (C). HRMS: cal.
for C22H22FN5OS2 456.12871, found 456.12867.
2-(3-(4-(Benzo[d]thiazol-2-yl)piperazin-1-yl)propylthio)-
5-(4-nitrophenyl)-1,3,4-oxadiazole (8l)
2-((3-(4-(Benzo[d]thiazol-2-yl)piperazin-1-yl)propyl)thio)-
5-(4-bromophenyl)-1,3,4-oxadiazole (8p)
1
Mp: 144–146 °C; H NMR (300 MHz, CDCl3) d: 2.01–
2.15 (q, 2H), 2.52–2.67 (m, 6H), 3.44 (t, 2H, J =
6.5 Hz), 3.59–3.71 (m, 4H), 7.03–7.11 (m, 1H), 7.24–7.31
(m, 1H), 7.45–7.64 (m, 1H), 8.21 (s, 1H), 8.22 (s, 1H), 8.37
(s, 1H), 8.39 (s, 1H). 13C NMR (CDCl3) d = 26.2 (CH2),
30.4 (CH2), 45.3 (2CH2), 52.1 (2CH2), 55.2 (CH2), 109.2
(CH), 113.6 (CH), 115.5 (2CH), 119.2 (2CH), 123.4 (CH),
124.3 (CH), 142.9 (C), 147.8 (C), 161.1 (C), 163.8 (C),
166.7 (C). HRMS: cal. for C22H22N6O3S2 483.12342, found
483.12328.
1
Mp: 143–145 °C; H NMR (300 MHz, CDCl3) d: 2.05–
2.16 (m, 2H), 2.53–2.64 (m, 6H), 3.51 (t, 2H, J = 7.6 Hz),
3.66–3.75 (m, 4H), 6.95–7.03 (m, 1H), 7.12 (t, 1H,
J = 7.5 Hz), 7.20 (d, 1H, J = 8.3 Hz), 7.30 (d, 1H,
J = 7.5 Hz), 7.44 (s, 1H), 7.56 (s, 1H), 7.72 (s, 1H), 7.78
(s, 1H). 13C NMR (CDCl3) d = 26.0 (CH2), 30.9 (CH2),
45.5 (CH2), 52.3 (CH2), 56.5 (CH2), 108.7 (CH), 118.2
(CH), 121.6 (CH), 123.4 (CH), 125.2 (CH), 128.6 (CH),
123