Synthesis and biological activity of new 2-amino-4-[3-methyl-3-(5,6,7,8- tetrahydro-2-naphthyl)cyclobutyl]thiazole derivatives

Article abstract of DOI:10.1007/s11178-005-0105-2

2-Amino-4-[3-methyl-3-(5,6,7,8-tetrahydro-2-naphthyl)cyclobutyl]thiazole was synthesized by reaction of 1-methyl-1-(5,6,7,8-tetrahydro-2-naphthyl)-3- chloroacetylcyclobutane with thiourea in ethanol, and its subsequent transformations afforded new derivatives which were tested in vitro for antibacterial activity against some bacteria using the disk diffusion technique.

Full text of DOI:10.1007/s11178-005-0105-2

Russian Journal of Organic Chemistry, Vol. 40, No. 12, 2004, pp. 1813–1818. From Zhurnal Organicheskoi Khimii, Vol. 40, No. 12, 2004, pp. 1861–1865.
Original English Text Copyright © 2004 by Koparır, Cansız, Ahmedzade.
Synthesis and Biological Activity
of New 2-Amino-4-[3-methyl-3-(5,6,7,8-tetrahydro-
2-naphthyl)cyclobutyl]thiazole Derivatives*
M. Koparır, A. Cansız, and M. Ahmedzade
Chemistry Department, Faculty of Arts and Sciences, Fırat University, Elazığ, 23119 Turkey
e-mail: mkoparir@hotmail.com
Received September 23, 2003
Abstract—2-Amino-4-[3-methyl-3-(5,6,7,8-tetrahydro-2-naphthyl)cyclobutyl]thiazole was synthesized by
reaction of 1-methyl-1-(5,6,7,8-tetrahydro-2-naphthyl)-3-chloroacetylcyclobutane with thiourea in ethanol, and
its subsequent transformations afforded new derivatives which were tested in vitro for antibacterial activity
against some bacteria using the disk diffusion technique.
The formation of substituted cyclobutanes in re-
actions of 6-chloro-4,5-epoxy-2-methyl-1-hexene with
aromatic hydrocarbons, such as benzene, toluene,
naphthalene, and mesitylene, has been reported [1–3].
Thiazole and its derivatives are biologically important
compounds. For example, molecules of vitamin B1 and
cocarboxylase coenzyme contain thiazole fragments
[4]; penicillin molecule includes a thiazolidine ring.
2-Aminothiazoles are known as biologically active
compounds with a broad range of activity, and they are
also used as intermediate products in the synthesis of
antibiotics and dyes [5]. Derivatives of 3-substituted
cyclobutanecarboxylic acid exhibit antiinflammatory
and antidepressant activity [6, 7], as well as liquid
Scheme 1.
Me
Cl
Me
Cl
Na2Cr2O7/H2SO4
25–26 h, r.t.
OH
O
I
II
H
N
NH2
NHR
Me
Me
N
N
H2NC(S)NH2
EtOH
RNCX, PhH
X
S
S
III
IVa–IVd
ArCHO
EtOH
Ar
S
N
CHAr
N
HSCH2COOH
PhH
Me
Me
N
N
O
S
S
Va–Vd
VIa–VId
IV, R = Et, X = O (a); R = i-Pr, X = O (b); R = Me, X = S (c); R = Ph, X = S (d); V, VI, Ar = 4-ClC6H4 (a), 4-O2NC6H4 (b),
4-MeOC6H4 (c), 2-hydroxy-1-naphthyl (d).
* The original article was submitted in English.
1070-4280/04/4012-1813 © 2004 MAIK “Nauka/Interperiodica”

KOPARIR et al.
Table 1. Yields, melting points, and elemental analyses of compounds IVa–IVd, Va–Vd, and VIa–VId
1814
Found, %
Calculated, %
Comp. Yield,
mp, °C
Formula
no.
%
C
H
N
C
H
N
65
73
57
80
55
70
65
70
58
62
55
65
232
240
245
299
227
219
205
233
176
193
217
211
68.23
68.89
64.90
69.50
71.16
69.52
75.66
76.83
65.25
64.27
68.01
70.35
7.12
7.78
6.96
6.47
5.72
6.16
6.49
6.45
5.90
5.48
6.37
5.91
11.34
10.75
11.19
09.33
06.44
09.45
06.69
05.99
05.36
08.41
05.25
05.17
C21H27N3OS
C22H29N3OS
C20H25N3S2
68.26
68.89
64.65
69.24
71.38
69.58
74.96
76.96
65.50
64.13
68.54
70.69
7.36
7.62
6.78
6.28
5.99
5.84
6.77
6.24
5.50
5.38
6.16
5.74
11.37
10.96
11.31
09.69
06.65
09.74
06.72
06.19
05.66
08.31
05.71
05.32
IVa
IVb
IVc
IVd
Va
C25H27N3S2
C25H25ClN2S
C25H25N3O2S
C26H28N2OS
C29H28N2OS
C27H27ClN2OS2
C27H27N3O3S2
C28H30N2O2S2
C31H30N2O2S2
Vb
Vc
Vd
VIa
VIb
VIc
VId
Table 2. 1H NMR spectra of compounds IVa–IVd, Va–Vd, and VIa–VId
Chemical shifts δ, ppm
Comp.
no.
CH2, m (naphthalene + CH, m (1H)
CH3, s
(3H)
5-H, s
(1H)
Harom, m
other protons
cyclobutane)
(cyclobutane)
6.86–7.06
(3H)
1.81–1.84 (4H)
2.76–2.80 (4H)
2.33–2.55 (4H)
3.38–3.50
1.51
5.96 1.56 t (3H, CH3CH2), 3.61 q (2H,
CH3CH2), 5.30–5.41 br.s (1H,
NHCH2); 5.52 s (1H, NH)
IVa
6.85–7.05
(3H)
1.82–1.86 (4H)
2.31–2.81 (8H)
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
3.37–3.52
1.49
1.51
1.50
1.53
1.50
1.50
1.53
1.53
1.53
1.53
1.53
5.97 1.55–1.59 d (6H, CH3), 5.31–5.40 br.s
IVb
IVc
IVd
Va
(1H, NHCH), 5.50 s (1H, NH)
6.85–7.05
(3H)
1.82–1.86 (4H)
2.31–2.81 (8H)
5.97 3.02 d (3H, CH3), 5.30–5.40 br.s
(1H, NHCH3), 5.50 s (1H, NH)
5.97 9.60–10.41 br.s (2H, NH)a
6.85–8.12
(8H)
1.82–1.86 (4H)
2.31–2.81 (8H)
6.80–7.55
(7H)
1.82–1.85 (4H)
2.33–2.81 (8H)
5.91 8 06 s (1H, N=CH)
6.81–7.61
(7H)
1.82–1.86 (4H)
2.33–2.81 (8H)
5.91 8.00 s (1H, N=CH)
Vb
6.80–7.55
(7H)
1.82–1.86 (4H)
2.33–2.81 (8H)
5.91 3.33 s (3H, OCH3), 7.99 s (1H, N=CH)
5.91 7 99 s (1H, N=CH), 13.61 s (1H, OH)
5.91 4 10 s (2H, CH2S)
Vc
6.82–7.56
(9H)
1.82–1.85 (4H)
2.33–2.81 (8H)
Vd
6.81–7.55
(7H)
1.81–1.85 (4H)
2.33–2.81 (8H)
VIa
VIb
VIc
VId
6.81–7.43
(7H)
1.81–1.85 (4H)
2.33–2.81 (8H)
5.91 3.81 s (3H, OCH3), 4.10 s (2H, CH2S)
5.91 4 10 s (2H, CH2S)
6.81–7.55
(7H)
1.81–1.85 (4H)
2.33–2.81 (8H)
6.82–7.56
(9H)
1.82–1.85 (4H)
2.33–2.81 (8H)
5.91 4.10 s (2H, CH2S), 13.58 s (1H, OH)
a
Exchanges with D2O.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 40 No. 12 2004

SYNTHESIS AND BIOLOGICAL ACTIVITY OF NEW 2-AMINO-...
1815
crystal properties [8]. Various thiazole derivatives
were shown to exert herbicidal [9], antiinflammatory
[10, 11], antimicrobial [12], and antiparasitic action
[13]. Schistosomiasis is a chronic and debilitating
disease which infects about 300 millions people in
tropical and subtropical regions [14].
ether, anhydrous CaCl2, KOH (Aldrich), anhydrous
AlCl3 (Riedel), Na2Cr2O7, and H2SO4 (Merck) were
used without additional purification. 6-Chloro-4,5-
epoxy-2-methyl-1-hexene was received from organic
chemists at the Department of Chemistry, University of
Fırat; it was distilled just before use. 2-Chloro-1-[3-
methyl-3-(5,6,7,8-tetrahydro-2-naphthyl)cyclobutyl]-
ethanol (I) was synthesized as described in [1].
In mammalian systems, molecular oxygen is
directly incorporated into naphthalene metabolism
[15]. Tetrahydronaphthalene may undergo biological
oxidation to a quinoid structure which is reponsible for
reduction of the rate of schistosoma glycolysis [16]. In
addition, tetrahydronaphthalene is capable of binding
molecular oxygen under mild conditions with forma-
tion of peroxy compounds [17]. Bushby et al. [18]
reported that some thiazoles and thiazolidin-4-ones are
biologically important as antimetabolites and schisto-
somicides.
2-Chloro-1-[3-methyl-3-(5,6,7,8-tetrahydro-2-
naphthyl)cyclobutyl]ethanone (II). A 1000-ml four-
necked flask was charged with 0.29 mol of Na2Cr2O7,
0.52 mol of compound I, and 50 ml of water, and
75 ml of 68% (by volume) sulfuric acid was added
dropwise under stirring over a period of 7–8 h, main-
taining the mixture at room temperature. The mixture
was stirred for about 18 h at room temperature, the
precipitate was filtered off, and the filtrate was extract-
ed with several portions of diethyl ether. The extract
was dried over anhydrous CaCl2, the solvent was dis-
tilled off, and the residue was distilled under reduced
pressure (1 mm) at 186°C. The distillate was passed
through a column charged with silica gel using ben-
zene–ethyl acetate (20:1) as eluent; Rf 0.48. Yield of II
~75%. IR spectrum, ν, cm–1: 1730 (C=O), 736 (C–Cl);
no OH absorption was present.
The present communication describes the synthesis
of 2-amino-4-[3-methyl-3-(5,6,7,8-tetrahydro-2-
naphthyl)cyclobutyl]thiazole (III) from 2-chloro-1-[3-
methyl-3-(5,6,7,8-tetrahydro-2-naphthyl)cyclobutyl]-
ethanol (I). Compound I was oxidized to 3-chloro-
acetylcyclobutane II which was brought into conden-
sation with thiourea to obtain 4-cyclobutyl-2-amino-
thiazole III. On the basis of compound III we syn-
thesized a number of derivatives IV–VI having urea,
thiourea, Schiff base, and thiazolidin-4-one fragments
(Scheme 1). The structure of the products was con-
2-Amino-4-[3-methyl-3-(5,6,7,8-tetrahydro-2-
naphthyl)cyclobutyl]thiazole (III). A solution of
2.76 g (10 mmol) of compound II in 30 ml of anhy-
drous ethanol was added dropwise under continuous
stirring to a solution of 0.76 g (10 mmol) of thiourea
in 50 ml of anhydrous ethanol, heated to 50–60°C. The
progress of the reaction was monitored by IR spec-
troscopy, following the disappearance of the carbonyl
absorption band of initial ketone II. The mixture was
made alkaline by adding 5% aqueous ammonia, and
the colorless precipitate was filtered off, washed with
aqueous ammonia and several portions of water, dried
in air, and recrystallized from aqueous ethanol (1:3).
Yield 74%. Colorless crystals, mp 222–223°C. IR
spectrum (KBr), ν, cm–1: 3285–3310 (NH2), 1604
1
firmed by elemental analysis and H NMR spectros-
copy (Tables 1, 2). Compound III characteristically
showed in the IR spectrum absorption bands at 3285
and 3310 (NH2), 1604 (C=N), and 685 cm–1 (C–S–C);
no absorption assignable to C–Cl or carbonyl vibra-
tions was present.
Table 3 contains the results of testing compounds
III–VI for antibacterial activity against some bacteria.
EXPERIMENTAL
The melting points were determined in open
capillaries using a Gallenkamp digital melting point
apparatus and were not corrected. The IR spectra were
recorded in KBr on a Mattson 1000 FT-IR spectrom-
1
(C=N), 685 (C–S–C). H NMR spectrum (CDCl3), δ,
ppm: 6.86–7.06 m (3H, Harom.), 5.95 s (1H, 5-H, thia-
zole), 5.48 s (2H, NH2), 3.52 quint (1H, CH, cyclo-
butane, J = 8.80 Hz), 2.76–2.80 m (4H, CH2, tetralin),
2.33–2.55 m (4H, CH2, cyclobutane), 1.81–1.84 m
1
eter. The H NMR spectra were obtained on JEOL FX
90 (90 MHz) and Bruker (200 MHz) instruments from
solutions in CDCl3–DMSO-d6 using TMS as internal
reference. The elemental compositions were deter-
mined on a LECO-CHNS-938 analyzer.
13
(4H, CH2, tetralin), 1.54 s (3H, CH3). C NMR spec-
trum (CDCl3), δC, ppm: 170.60 (C1), 157.85 (C2),
152.09 (C3), 42.55 (C4), 40.18 (C5), 32.66 (C6), 31.50
(C7), 31.05 (C8), 138.87 (C9), 136.18 (C10), 131.04
(C11), 127.52 (C12), 124.30 (C13), 102.27 (C14), 25.35
1,2,3,4-Tetrahydronaphthalene (Aldrich) was dried
over anhydrous magnesium sulfate prior to use. Diethyl
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 40 No. 12 2004

KOPARIR et al.
1816
Table 3. Antibacterial activity of thiazole derivatives IVa–IVd, Va–Vd, and VIa–VId (inhibition zone, mm)a
Comp. Concentra-
no.
IVa
IVb
IVc
IVd
Va
tion, µg
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
100
200
400
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
01
–
05
–
06
–
05
–
05
–
07
–
09
–
01
–
09
–
06
–
06
–
01
–
08
–
08
–
09
–
05
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
08
–
05
–
07
–
06
–
06
–
06
–
01
–
08
–
09
–
07
–
06
–
09
–
07
–
08
–
01
–
05
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
07
–
06
–
06
–
05
–
05
–
07
–
08
–
06
–
08
–
07
–
07
–
09
–
08
–
07
–
01
–
06
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
06
–
05
–
07
–
05
–
06
–
07
–
07
–
07
–
09
–
06
–
07
–
08
–
09
–
08
–
01
–
05
–
–
–
05
13
–
–
–
–
–
–
05
13
–
–
06
12
–
–
–
–
–
–
11
–
07
–
11
–
07
–
12
–
11
–
10
–
12
–
12
–
11
–
11
–
10
–
07
–
Vb
–
–
06
13
–
–
–
–
05
16
–
–
07
14
–
–
07
16
–
–
–
05
16
–
–
–
14
–
6
14
–
07
–
14
–
15
–
13
–
15
–
15
–
15
–
09
–
–
Vc
–
–
05
11
–
–
–
–
06
12
–
–
06
14
–
–
06
13
–
–
–
–
–
–
12
–
06
–
10
–
07
–
11
–
12
–
12
–
12
–
14
–
13
–
12
–
05
–
Vd
–
–
06
12
–
–
–
–
05
12
–
–
05
12
–
–
06
11
–
–
–
–
–
–
10
–
05
–
09
–
05
–
10
–
10
–
11
–
11
–
12
–
12
–
10
–
06
–
VIa
VIb
VIc
VId
–
–
07
13
–
–
–
–
05
12
–
–
06
13
–
–
06
13
–
–
–
–
–
–
12
–
06
–
13
–
06
–
10
–
12
–
12
–
11
–
11
–
13
–
12
–
06
–
–
–
05
12
–
–
–
–
05
12
–
–
06
13
–
–
05
12
–
–
–
–
–
–
11
–
05
–
11
–
05
–
11
–
13
–
12
–
10
–
11
–
10
–
10
–
06
–
–
–
05
13
–
–
–
–
05
12
–
–
–
–
05
10
–
–
–
–
–
–
09
–
05
–
10
–
06
–
11
–
11
–
09
–
09
–
09
–
09
–
10
–
09
–
06
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
–
06
04
07
07
05
06
08
08
07
07
09
07
08
08
09
05
Standards:
Ampicillin (10 µg)
12 NP 13
10 NP 13
12
09
16
20
34
14
19
17
12
10
Nystatin (30 µg)
NP 18 NP NP 15 NP NP NP NP NP NP NP NP NP NP NP
a
Dash denotes the absence of inhibition zone, and NP stands for “not performed.”
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 40 No. 12 2004

SYNTHESIS AND BIOLOGICAL ACTIVITY OF NEW 2-AMINO-...
1817
(C15), 25.31 (C16). Found, %: C 72.10; H 7.41; N 8.93;
S 10.68. C18H22N2S. Calculated, %: C 72.44; H 7.43;
N 9.39; S 10.74.
ml), ensuring homogeneous distribution of the food
medium over Petri dishes. The disks injected with the
extracts were placed on the solid agar medium and
were slightly pressed [19–23].
4-[3-Methyl-3-(5,6,7,8-tetrahydro-2-naphthyl)-
cyclobutyl]-2-ureido(thioureido)thiazoles IVa–IVd
(general procedure). A mixture of 2.98 g (0.01 mol) of
compound III and 0.01 mol of the corresponding iso-
cyanate or isothiocyanate in anhydrous benzene was
heated for 6 h under reflux. After cooling, the precip-
itate was filtered off and recrystallized from methanol.
The Petri dishes prepared as described above were
kept for 2 h at 4°C; samples inoculated with yeasts
were incubated for 24–36 h at 25±0.1°C, and bacteria
were incubated for 18–20 h at 35°C. The inhibition
zones formed on the food medium were evaluated in
millimeters. Each experiment was performed in three
parallel runs.
2-Arylmethyleneamino-4-[3-methyl-3-(5,6,7,8-
tetrahydro-2-naphthyl)cyclobutyl]thiazoles Va–Vd
(general procedure). A solution of 2.98 g (0.01 mol) of
compound III in 40 ml of anhydrous ethanol was
added dropwise under continuous stirring to a solution
of 0.01 mol of the corresponding aromatic aldehyde in
20 ml of anhydrous ethanol. The mixture was stirred
for 10 h at 60–70°C, cooled, and poured into ice water.
The precipitate was filtered off and recrystallized from
ethanol.
The newly synthesized thiazole derivatives were
tested in vitro for antimicrobial activity against the
following bacteria: Salmonella thypimurium TA 100 hi,
Kluyveromyses fragilis, Serratia marcescens NRRL
3284, Pseudomonas aeruginosa ATCC 27, Rhodo-
torula rubrum, Aeromonas hydrophila ATCC 7966,
Enterococcus faecalis ATCC 15, Corynebacterium
xerosis UC 9165, Enterobacter aerogenes RA 2971,
Bacillus megaterium DSM 32, Listeria monocytogenes
Scoot A, Proteus vulgaris FMC 1, Mycobacterium
smegmatis CCM 2067, Bacillus subtilis IMG 22,
Staphylococcus aureus Cowan 1, and Escherichia coli
DM. The diameters of the inhibition zones were
measured at doses of 100, 200, and 400 µg; the results
are summarized in Table 3. No antibacterial effect was
observed for all the examined compounds at a dose of
100 µg. At 200 µg, only compounds Va–Vd and VIa–
VIc showed antimicrobial effect against some micro-
organisms. The best effect was observed for all com-
pounds at a dose of 400 µg (Table 3).
2-Aryl-3-{4-[3-methyl-3-(5,6,7,8-tetrahydro-2-
naphthyl)cyclobutyl]thiazol-2-yl}tetrahydrothiazol-
4-ones VIa–VId (general procedure). A solution of
0.1 ml (0.01 mol) of sulfanylacetic acid in 10 ml of
anhydrous benzene was added under vigorous stirring
to a solution of 0.01 mol of compound Va–Vd in 60 ml
of anhydrous benzene. The mixture was heated for 6 h
under reflux, the solvent was removed under reduced
pressure, and the residue was treated with warm
petroleum ether. The precipitate was filtered off and
recrystallized from ethanol.
This study was supported by FUNAF (grant
no. 477; Elazığ, Turkey). The authors are thankful to
Assoc. Prof. Dr. Metin Dığrak for his help in the deter-
mination of biological activity.
The yields, melting points, and analytical data of
compounds IVa–IVd, Va–Vd, and VIa–VId are given
in Table 1, and their 1H NMR spectra, in Table 2.
Preparation of microorganism cultures. All
samples to be tested and standard antibiotics were
injected into empty sterilized antibiotic disks (6 mm in
diameter; Schleicher & Shull No. 2668, Germany) in
an amount of 100, 200, or 400 µg. Disks injected with
chloroform were used as control. All the bacteria listed
below were incubated at 30±0.1°C over a period of
24 h by inoculation into Nutrient Broth (Difco), and
the yeasts were incubated in Sabourand Dextrose
Broth (Difco) over a period of 24 h. Mueller Hinton
Agar (oxoid) and Sabourand Dextrose Agar were
sterilized in a flask, cooled to 45–50°C, and distributed
over sterilized Petri dishes (9 cm in diameter) in
an amount of 15 ml using a pipette in 24 h after
injecting cultures of bacteria and yeasts in an amount
of 0.1 ml (105 bacteria per ml or 104 yeast cells per
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