Month 2014
Hybrid Class Phenylthiazole and 1,2,3,4-Tetrahydronaphthalene Target Sertraline
Transporter for Antidepressant Action Revealed by Docking Studies
(
Bruker Bioscience, Billerica, MA, USA) in CDCl3 using
3030 C–H stretching, 1614 C═C Aromatic (narrow), 3212
Secondary N–H, 3410 OH naphthalene; 1H-NMR (Bruker
tetramethylsilane as an internal standard (chemical shift in δ ppm).
Elemental analysis was carried out on a Vario EL III elemental
analyzer (Elementar Analysensysteme, GmbH, Germany).
Avance II 400 NMR spectrometer): 1.71 (m, 2H, 3-CH
naphthalene), 2.90 (t, 2H, 4-CH naphthalene), 3.60 (m, 1H, 2-
2
2
1
-[4-(4′-Chlorophenyl)-thiazole-2-ylamino]-1,2,3,4-tetrahydro-
naphthalen-2-ol (AU-1). Physical state: Light yellow crystals;
Yield: 72%; mp 287–289°C; R value: 0.6342 Hexane: Ethylacetate
CH naphthalene), 3.68 (d, 1H, J = 7.2, 2-OH naphthalene),
4.12 (t, 1H, 1-CH naphthalene), 4.67 (d, 1H, NH-thiazole),
6.98–7.12 (d, 4H, 5-, 6-, 7-, and 8-CH-naphthalene), 7.36 (s,
1H, 4-CH thiazole), 7.65 (d, 2H, 3,5-CH phenyl), 8.04 (d,2H,
2,6-CH phenyl); C-NMR (Bruker Avance II 100 NMR
spectrometer): δ ppm 25.71, 27.15, 60.98, 80.52, 100.65,
121.65, 128.46, 135.96, 138.24, 139.24, 148.37, 148.79,
165.02; CHN Elemental analysis (Vario EL III): Calcd: C,
62.11; H, 4.66; N, 11.44/Found: C, 61.90; H, 4.46; N, 11.28
1-[4-(4′-Hydroxyphenyl)thiazol-2-ylamino]-1,2,3,4-tetrahydro-
naphthalen-2-ol (AU-5). Physical state: Light yellow oil; Yield:
f
(
19:1); FTIR: 1660 C═C (strong), 1488 C═C Aromatic (narrow),
712 C═N stretching, 3025 C–H stretching, 1600 C═C Aromatic
narrow), 3205 Secondary N–H, 3400 OH naphthalene; H-NMR
Bruker Avance II 400 NMR spectrometer): δ ppm 1.71 (m, 2H, 3-
CH2 naphthalene), 2.90 (t, 2H, 4-CH2 naphthalene), 3.60 (m, H,
-CH naphthalene), 3.68 (d, 1H, J= 7.1, 2-OH naphthalene), 4.12
t, 1H, 1-CH naphthalene), 4.67 (d, 1H, NH-thiazole), 6.98–7.12
d, 4 × 1H, 5 , 6 , 7 , and 8 CH naphthalene), 7.36 (s, 1H,4-CH
thiazole), 7.65 (d,2H, 3,5-CH phenyl), 8.04 (d,2H, 2,6-CH phenyl);
C-NMR (Bruker Avance II 100 NMR spectrometer): δ ppm
5.37, 26,75, 60.64, 80.09, 99.98, 148.22, 128.88, 129.43,
31.23, 135.55, 137.88, 164.49; CHN elemental analysis
1
3
1
(
1
(
1
2
(
(
f
52%; bp 282–285°C; R value: 0.6845 Hexane: Ethylacetate (19:1);
FTIR (Shimadzu IRP-21): 1652 C═C (strong), 1481 C═C
Aromatic (narrow), 1704 C═N stretching, 3018 C–H stretching,
13
2
1
(
1596 C═C Aromatic (narrow), 3200 Secondary N–H, 3398 OH
1
Vario EL III): Calcd: C, 63.95; H, 4.80; N, 7.85/Found:
C, 63.58; H, 4.98; N, 7.68.
-[4-Phenylthiazol-2-ylamino]-1,2,3,4-tetrahydro-naphthalen-
-ol (AU-2). Physical state: Brownish green crystals; Yield:
6%; mp 294–296°C; R value: 0.6145 Hexane: Ethylacetate
naphthalene;
H-NMR (Bruker Avance II 400 NMR
naphthalene), 2.91 (t, 2H, 4-
spectrometer): 1.70 (m, 2H, 3-CH
2
1
CH naphthalene), 3.59 (m, 1H, 2-CH naphthalene), 3.67 (d, 1H,
2
2
J = 7.2, 2-OH naphthalene), 4.11 (t, 1H, 1-CH naphthalene), 4.66
(d, 1H, NH-thiazole), 5.48 (s, 1H, OH-phenyl), 6.96–7.10 (d, 4H,
7
f
(
19:1); FTIR (Shimadzu IRP-21): 1640 C═C (strong), 1462
5-, 6-, 7-, and 8-CH-naphthalene), 7.35 (s, 1H, 4-CH thiazole),
13
C═C Aromatic (narrow), 1700 C═N stretching, 3015 C–H
stretching, 1605 C═C Aromatic (narrow), 3203 Secondary N–H,
3
6.94 (d,2H, 3,5-CH phenyl), 7.82 (d,2H, 2,6-CH phenyl); C-
NMR (Bruker Avance II 100 NMR spectrometer): δ ppm 24.83,
26.25, 60.10, 79.64, 99.41, 116.42, 125.75, 128.90, 135.08,
137.39, 147.85, 164.04; CHN Elemental analysis (Vario EL III)
Calcd: C, 67.43; H, 5.36; N, 8.28/Found: C, 67.18; H, 5.58; N, 8.65.
1-[4-(4′-Bromophenyl)thiazol-2-ylamino]-1,2,3,4-tetrahydro-
naphthalen-2-ol (AU-6). Physical state: Light green powder;
1
395 OH naphthalene; H-NMR (Bruker Avance II 400 NMR
spectrometer): δ ppm 1.68 (m, 2H, 3-CH
t, 2H, 4-CH naphthalene), 3.57 (m, 1H, 2-CH naphthalene),
.64 (d, 1H, J = 7.2, 2-OH naphthalene), 4.08 (t, 1H, 1-CH
naphthalene), 4.63 (d, 1H, NH-thiazole), 6.94–7.06 (d, 4 × 1H, 5-,
-, 7-, and 8-CH-naphthalene), 7.33 (s, 1H,4-CH thiazole), 7.50
t,1H, 4-CH phenyl), 7.60 (t, 2H, 3,5-CH phenyl), 7.94 (d,2H,
2
naphthalene), 2.87
(
3
2
Yield: 67%; mp 214–216°C;
Ethylacetate (19:1); FTIR (Shimadzu IRP-21): 1651 C═C
strong), 1480 C═C Aromatic (narrow), 1704 C═N stretching, 3015
f
R value: 0.6662 Hexane:
6
(
2
1
3
(
,6-CH phenyl);
C-NMR (Bruker Avance II 100 NMR
C–H stretching, 1599 C═C Aromatic (narrow), 3201 Secondary N–
spectrometer): δ ppm 25.42, 26.85, 60.69, 80.14, 100.04, 127.52,
29.46, 133.12, 135.62, 137.92, 148.78, 164.58; CHN Elemental
1
H; H-NMR (Bruker Avance II 400 NMR spectrometer): 1.71 (m,
1
2
H, 3-CH naphthalene), 2.92 (t, 2H, 4-CH naphthalene), 3.60 (m,
analysis (Vario EL III): Calcd: C, 70.78; H, 5.63; N, 8.69/Found:
C, 70.43; H, 5.92; N, 8.51.
2
2
1H, 2-CH naphthalene), 3.69 (d, 1H, J= 7.1, 2-OH naphthalene),
4.12 (t, 1H, 1-CH naphthalene), 4.66 (d, 1H, NH-thiazole), 6.98–
1
-[4-(4′-Methoxyphenyl)thiazol-2-ylamino]-1,2,3,4-tetrahydro-
naphthalen-2-ol (AU-3). Physical state: Brownish green oil;
Yield: 71%; bp 263–265°C; Rf value: 0.6226 Hexane:
Ethylacetate (19:1); FTIR (Shimadzu IRP-21): 1657 C═C
7.12 (d, 4H, 5-, 6-, 7-, and 8-CH-naphthalene), 7.38 (s, 1H, 4-CH
thiazole), 6.96 (d,2H, 3,5-CH phenyl), 7.85 (d,2H, 2,6-CH phenyl);
C-NMR (Bruker Avance II 100 NMR spectrometer): δ ppm
13
(
3
strong), 1484 C═C Aromatic (narrow), 1708 C═N stretching,
25.41, 26.84, 60.68, 80.13, 100.05, 116.42, 129.77,132.16,132.28,
148.19, 164.57; CHN Elemental analysis (Vario EL III) Calcd: C,
56.86; H, 4.27; N, 6.98/Found: C, 56.65; H, 4.39; N, 7.08.
018 C–H stretching, 1590 C═C Aromatic (narrow), 3200
1
Secondary N–H; 3398 OH naphthalene; H-NMR (Bruker
Avance II 400 NMR spectrometer): 1.68 (m, 2H, 3-CH2
1-[4-(3′-Hydroxyphenyl)thiazol-2-ylamino]-1,2,3,4-tetrahydro-
naphthalen-2-ol (AU-7). Physical state: Yellow powder; Yield:
naphthalene), 2.87 (t, 2H, 4-CH naphthalene), 3.57 (m, 1H, 2-
2
CH naphthalene), 3.64 (d, 1H, J = 7.2 2-OH naphthalene), 3.85
64%; mp 280–282°C; R value: 0.6787 Hexane: Ethylacetate
f
(
s, 3H, CH3-O phenyl), 4.08 (t, 1H, 1-CH naphthalene), 4.63
(19:1); FTIR (Shimadzu IRP-21): 1650 C═C (strong), 1482 C═C
Aromatic (narrow), 1706 C═N stretching, 3013 C–H stretching,
1597 C═C Aromatic (narrow), 3200 Secondary N–H, 3398
(d, 1H, NH-thiazole), 6.94–7.06 (d, 4H, 5-, 6-, 7-, and 8-CH-
naphthalene), 7.34 (s, 1H,4-CH thiazole), 7.50 (d,2H, 3,5-CH
phenyl), 7.94 (d,2H, 2,6-CH phenyl); C-NMR (Bruker Avance
1
3
1
OH naphthalene; H-NMR (Bruker Avance II 400 NMR
II 100 NMR spectrometer): δ ppm 24.83, 26.23, 55.92, 60.07,
spectrometer): 1.70 (m, 2H, 3-CH
2
naphthalene), 2.91 (t, 2H, 4-
7
9.62, 99.39, 114.79, 125.43, 128.48, 135.05, 137.36, 147.83,
CH naphthalene), 3.58 (m, 1H, 2-CH naphthalene), 3.67 (d, 1H,
2
1
60.70, 164.01; CHN Elemental analysis (Vario EL III): Calcd:
J = 7.1, 2-OH naphthalene), 4.10 (t, 1H, 1-CH naphthalene), 4.65
(d, 1H, NH-thiazole), 6.99–7.10 (d, 4H, 5-, 6-, 7-, and 8-CH-
naphthalene), 7.38 (s, 1H, 4-CH thiazole), 6.65 (d, 1H, 4-CH
phenyl), 6.94 (d,2H, 2-CH phenyl), 7.08 (d, 1H, 6-CH phenyl),
7.66 (d, 1H, 5-CH phenyl); C-NMR (Bruker Avance II 100
NMR spectrometer): δ ppm 25.44, 26.86, 61.70, 80.15, 100.05,
112.88, 115.92, 120.09, 130.71, 134.57, 135.63, 137.94,
C, 68.16; H, 5.72; N, 7.95/Found: C, 68.52; H, 5.81; N, 7.58.
-[4-(4′-Nitrophenyl)thiazol-2-ylamino]-1,2,3,4-tetrahydro-
naphthalen-2-ol (AU-4). Physical state: Light green crystals;
Yield: 65%; mp 287–289°C; Rf value: 0.6897 Hexane:
Ethylacetate (19:1); FTIR (Shimadzu IRP-21): 1672 C═C
1
1
3
(
strong), 1495 C═C Aromatic (narrow), 1722 C═N stretching,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet