RCHH HARM
A P
Arch. Pharm. Chem. Life Sci. 2015, 348, 34–45
Antidepressant Activity of 5-HT3 Antagonists
Archiv der Pharmazie
8.16–8.0 (m, 2H, naphthyridine), 7.45–7.35 (m, 1H, naphthyr-
idine), 7.31–7.26 (m, 2H, phenyl), 7.0–6.89 (m, 3H, phenyl),
4.82–4.57 (q, 2H, -OCH2), 4.13–3.90 (m, 2H, piperazine), 3.58–
3.40 (m, 2H, -piperazine), 3.34–3.29 (m, 2H, piperazine), 3.22–
3.05 (m, 2H, piperazine), 1.51–1.38 (t, 3H, -CH3 of ethoxy). ESI-
MS: m/z 363 [MþH] 100%.
(m, 2H, piperazine), 3.15–3.05 (m, 2H, piperazine), 1.50–1.37 (t,
3H, -CH3 of ethoxy). ESI-MS: m/z 397.1 [MþH] 100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(2-methoxyphenyl)pipera-
zin-1-yl]methanone 8g: IR (KBr/cm): 3150, 3050, 1630, 1560,
1478, 1135, 1038. 1H NMR, CDCl3, d (ppm): 9.04–8.92 (m, 1H,
naphthyridine), 8.19–8.06 (m, 2H, naphthyridine), 7.45–7.33
(m, 1H, naphthyridine), 7.15–7.02 (m, 1H, phenyl), 6.99–6.85
(m, 3H, phenyl), 4.86–4.54 (q, 2H, -OCH2), 4.18–3.96 (m, 2H,
piperazine), 3.83 (s, 3H, -OCH3), 3.61–3.36 (m, 2H, -piperazine),
3.31–3.13 (m, 2H, piperazine), 3.11–2.93 (m, 2H, piperazine),
1.54–1.40 (t, 3H, -CH3 of ethoxy). ESI-MS: m/z 393.1 [MþH]
100%.
2-Ethoxy-1,8-naphthyridin-3-yl(4-benzylpiperazin-1-yl)metha-
none 8b: IR (KBr)/cm: 3110, 3050, 1620, 1554, 1483, 1034. 1H
NMR, CDCl3, d (ppm): 9.03–8.92 (m, 1H, naphthyridine), 8.17–
7.99 (m, 2H, naphthyridine), 7.47–7.35 (m, 2H, naphthyridine,
phenyl), 7.31–7.19 (m, 4H, phenyl), 4.81–4.54 (m, 2H, -OCH2),
3.96–3.76 (m, 2H, piperazine), 3.64–3.48 (m, 2H, -piperazine),
3.43–3.17 (m, 2H, piperazine), 2.69–2.48 (m, 2H, piperazine),
2.42–2.30 (m, 2H, piperazine), 1.52–1.37 (t, 3H, -CH3 of ethoxy).
ESI-MS: m/z 377.26 [MþH] 100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(3-methoxyphenyl)pipera-
zin-1-yl]methanone 8h: IR (KBr/cm): 3150, 3050, 1630, 1560,
1470, 1142, 1038. 1H NMR, CDCl3, d (ppm): 8.98–8.92 (m, 1H,
naphthyridine), 8.19–8.06 (m, 2H, naphthyridine), 7.45–7.30
(m, 1H, naphthyridine), 7.20–7.10 (m, 1H, phenyl), 6.59–6.45
(m, 1H, phenyl), 6.48–6.35 (m, 2H, phenyl), 4.66–4.50 (q, 2H,
-OCH2), 4.18–3.98 (m, 2H, piperazine), 3.73 (s, 3H, OCH3), 3.48–
3.36 (m, 2H, -piperazine), 3.31–3.20 (m, 2H, piperazine), 3.15–
2.97 (m, 2H, piperazine), 1.48–1.40 (t, 3H, -CH3 of ethoxy). ESI-
MS: m/z 393.1 [MþH] 100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(4-nitrophenyl)piperazin-1-
yl]methanone 8c: IR (KBr/cm): 3100, 3060, 1628, 1570, 1460,
1142, 1035. 1H NMR, CDCl3, d (ppm): 9.07–8.98 (m, 1H,
naphthyridine), 8.21–8.09 (m, 4H, naphthyridine, phenyl),
7.49–7.40 (m, 1H, naphthyridine), 6.90–6.78 (m, 2H, phenyl),
4.83–4.63 (q, 2H, -OCH2), 4.17–3.84 (m, 2H, piperazine),
3.65–3.58 (m, 2H, -piperazine), 3.49–3.34 (m, 4H, piperazine),
1.49–1.42 (t, 3H, -CH3 of ethoxy). ESI-MS: m/z 406 [MþH]
100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(2-methylphenyl)pipera-
zin-1-yl]methanone 8i: IR (KBr)/cm: 3100, 3050, 1620, 1500,
1460, 1350. 1H NMR, CDCl3, d (ppm): 8.99–8.92 (m, 1H,
naphthyridine), 8.19–8.06 (m, 2H, naphthyridine), 7.41–7.36
(m, 1H, naphthyridine), 7.21–7.14 (m, 2H, phenyl), 7.04–6.96
(m, 2H, phenyl), 4.78–4.62 (q, 2H, -OCH2), 4.12–3.89 (m, 2H,
piperazine), 3.76–3.65 (m, 2H, piperazine), 3.58–3.32 (m, 2H,
-piperazine), 3.11–2.77 (m, 2H, piperazine), 2.33 (s, 3H, CH3),
1.52–1.46 (t, 3H, -CH3 of ethoxy). ESI-MS: m/z 377.1 [MþH]
100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(2-chlorophenyl)piperazin-
1-yl]methanone 8d: IR (KBr/cm): 3120, 3060, 1628, 1570, 1460,
1137, 1035. 1H NMR, CDCl3, d (ppm): 9.01–8.85 (m, 1H,
naphthyridine), 8.17–7.93 (m, 2H, naphthyridine), 7.38–7.26
(m, 2H, naphthyridine, phenyl), 7.20–7.14 (m, 1H, phenyl),
7.05–6.86 (m, 2H, phenyl), 4.75–4.54 (q, 2H, -OCH2), 4.09–3.83
(m, 2H, piperazine), 3.49–3.28 (m, 2H, -piperazine), 3.15–3.07
(m, 2H, piperazine), 3.04–2.84 (m, 2H, piperazine), 1.48–1.34 (t,
3H, -CH3 of ethoxy). ESI-MS: m/z 397 [MþH] 100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(4-methylphenyl)pipera-
zin-1-yl]methanone 8j: IR (KBr)/cm: 3100, 3060, 1620, 1550,
1430, 1340. 1H NMR, CDCl3, d (ppm): 9.09–8.93 (m, 1H,
naphthyridine), 8.23–8.03 (m, 2H, naphthyridine), 7.50–7.38
(m, 1H, naphthyridine), 7.21–7.02 (m, 2H, phenyl), 6.94–6.77
(m, 2H, phenyl), 4.82–4.57 (q, 2H, -OCH2), 4.13–3.92 (m, 2H,
piperazine), 3.56–3.37 (m, 2H, piperazine), 3.30–3.24 (m, 2H,
-piperazine), 3.17–2.98 (m, 2H, piperazine), 2.29 (s, 3H, CH3),
1.50–1.39 (t, 3H, -CH3 of ethoxy). ESI-MS: m/z 377.1 [MþH]
100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(3-chlorophenyl)piperazin-
1-yl]methanone 8e: IR (KBr/cm): 3100, 3060 (aromatic C–H
–
–
–
str.), 1628 (C O str.of amide), 1570, 1460 (C C, C N ring str.),
–
–
–
1137, 1035 (C–O–C str. of aryl alkyl ether). 1H NMR, CDCl3, d
(ppm): 9.04–8.95 (m, 1H, naphthyridine), 8.18–8.08 (m, 2H,
naphthyridine), 7.47–7.36 (m, 1H, naphthyridine), 7.25–7.13
(m, 1H, phenyl), 6.94–6.84 (m, 2H, phenyl), 6.82–6.76 (m, 1H,
phenyl), 4.82–4.60 (q, 2H, -OCH2), 4.09–3.87 (m, 2H, pipera-
zine), 3.57–3.40 (m, 2H, -piperazine), 3.29–3.19 (m, 2H,
piperazine), 3.12–3.03 (m, 2H, piperazine), 1.50–1.41 (t, 3H,
-CH3 of ethoxy). ESI-MS: m/z 397.1 [MþH] 100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)(4-methyl)piperazin-1-yl)-
methanone 8k: IR (KBr)/cm: 3100, 3070, 1620, 1550, 1435,
1340. 1H NMR, CDCl3, d (ppm): 9.06–8.98 (m, 1H, naphthyr-
idine), 8.25–8.18 (m, 1H, naphthyridine), 7.98–7.86 (m, 1H,
naphthyridine), 7.41–7.34 (m, 1H, naphthyridine), 4.75–4.57 (q,
2H, -OCH2), 4.10–3.95 (m, 2H, piperazine), 3.58–3.34 (m, 2H,
piperazine), 3.28–3.24 (m, 2H, -piperazine), 3.10–2.97 (m, 2H,
piperazine), 2.96 (s, 3H, CH3), 1.50–1.35 (t, 3H, -CH3 of ethoxy).
ESI-MS: m/z 301 [MþH] 100%.
(2-Ethoxy-1,8-naphthyridin-3-yl)[4-(4-chlorophenyl)piperazin-
1-yl]methanone 8f: IR (KBr/cm): 3100, 3060, 1628, 1570, 1460,
1142, 1035. 1H NMR, CDCl3, d (ppm): 9.03–8.96 (m, 1H,
naphthyridine), 8.16–8.0 (m, 1H, naphthyridine), 7.45–7.38 (m,
1H, naphthyridine), 7.35–7.26 (m, 3H, naphthyridine, phenyl),
6.90–6.69 (m, 2H, phenyl), 4.80–4.60 (q, 2H, -OCH2), 4.10–3.90
(m, 2H, piperazine), 3.52–3.40 (m, 2H, -piperazine), 3.30–3.20
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