Synthesis and biological study of some 4-oxo-thiazolidine derivatives of 2-aminothiazole

Article abstract of DOI:10.1002/cjoc.201190171

Conventional and microwave assisted synthesis of new series of N-[2-{2-(substituted phenyl)-4-oxo-5-(substituted benzylidene)-1,3-thiazolidine} -iminoethyl]-2-aminothiazole 5a - 5m have been developed. The cycloaddition reaction of thioglycolic acid with N-{2-(substituted benzylidenehydrazino)- ethyl}-2-aminothiazole 3a - 3m in the presence of anhydrous ZnCl2 afforded new heterocyclic compounds N-[2-{2-(substituted phenyl)-4-oxo-1,3-thiazolidine}- iminoethyl]-2-aminothiazole 4a - 4m. The later product on treatment with several selected substituted aromatic aldehydes in the presence of C₂H ₅ONa undergoes Knoevenagel reaction to yield 5a - 5m. The structures of compounds 1, 2, 3a - 3m, 4a - 4m and 5a - 5m were confirmed by IR, ¹H NMR, ¹³C NMR, FAB-Mass and chemical analysis. All above compounds were screened for their antimicrobial activities against some selected bacteria and fungi and antituberculosis study against M. tuberculosis.

Full text of DOI:10.1002/cjoc.201190171

FULL PAPER
Synthesis and Biological Study of Some 4-oxo-Thiazolidine
Derivatives of 2-Aminothiazole
Samadhiya, Pushkal*
Sharma, Ritu
Srivastava, Santosh K.
Srivastava, Savitri D.
Synthetic Organic Chemistry Laboratory, Department of Chemistry, Dr. H.S. Gour University
(A Central University), Sagar, M.P., 470003 India
Conventional and microwave assisted synthesis of new series of N-[2-{2-(substituted phenyl)-4-oxo-
5-(substituted benzylidene)-1,3-thiazolidine}-iminoethyl]-2-aminothiazole 5a— 5m have been developed. The
cycloaddition reaction of thioglycolic acid with N-{2-(substituted benzylidenehydrazino)-ethyl}-2-aminothiazole
3a— 3m in the presence of anhydrous ZnCl2 afforded new heterocyclic compounds N-[2-{2-(substituted phenyl)-
4-oxo-1,3-thiazolidine}-iminoethyl]-2-aminothiazole 4a— 4m. The later product on treatment with several selected
substituted aromatic aldehydes in the presence of C2H5ONa undergoes Knoevenagel reaction to yield 5a— 5m. The
structures of compounds 1, 2, 3a— 3m, 4a— 4m and 5a— 5m were confirmed by IR, 1H NMR, 13C NMR,
FAB-Mass and chemical analysis. All above compounds were screened for their antimicrobial activities against
some selected bacteria and fungi and antituberculosis study against M. tuberculosis.
Keywords conventional, microwave, synthesis, 2-aminothiazole, 4-oxo-thiazolidine, antimicrobial, antitubercular
Introduction
sized compounds 5a—5m were screened for their an-
timicrobial activities against some selected bacteria and
fungi and antituberculosis study against M. tuberculosis.
Thiazoles and their derivatives have attracted con-
tinuing interest over the years because of their varied
biological activities. They have recently found applica-
tion in drug development for the treatment of anti-in-
flammatory,1,2 antituberculosis,3 antiprotozoal,4 anti-
cancer,5 anticonvulsants,6 antifungal,7 anti-HIV8 and
antibacterial.7,9 Some thiazole derivatives are used in
clinical practice as antipsychotic,10 and anticoccidial
agents.11 4-thiazolidine derivatives constitution is an
important class of heterocyclic compounds for their po-
tential pharmaceutical applications. Consequently, a
large number of synthetic protocols leading to the com-
pounds have been reported in this literature. Heterocy-
cles containing thiazolidine moity are of interest be-
cause they show some pharmacological and biological
activities. Thiazolidines derivatives were reported to
possess antifungal,12,13 antibacterial, antiinflamma-
tory,14,15 herbicidal,16 antibiotic agents,17 antidiabetic18
and analgesic19 activities etc. All above biological ac-
tivities of thiazole and thiazolidine derivatives aroused
our attention and promoted us to synthesize a new series
of N-[2-{2-(substituted phenyl)-4-oxo-5-(substituted ben-
zylidene)-1,3-thiazolidine}-iminoethyl]-2-aminothiazole,
5a—5m by conventional and microwave methods. The
structures of compounds 1, 2, 3a—3m, 4a—4m and
Experimental
Melting points were taken in open capillaries and
uncorrected. Progress of reaction was monitored by sil-
ica gel-G coated TLC plates in MeOH/CHCl3 system
(1∶9, volume ratio). The spot was visualized by ex-
posing dry plate in iodine vapours chamber. IR spectra
were recorded in KBr disc on a Schimadzu 8201 PC
－
1
1
FTIR spectrophotometer (vmax in cm ) and H and 13C
NMR spectra were measured on a Brucker DRX-300
spectrometer in CDCl3 at 300 and 75 MHz respectively
using TMS as an internal standard. All chemical shifts
were reported on δ scales. The FAB-Mass spectra were
recorded on a Jeol SX-102 mass spectrometer. Elemen-
tal analyses were performed on a Carlo Erba-1108 ana-
lyzer. Microwave irradiation was carried out in open
glass vessel. Modified microwave oven (800 W) was
used for the synthesis of compounds. A thermocouple
was used to monitor the temperature inside the vessel of
the microwave. The analytical data of all the com-
pounds were highly satisfactory. For column chroma-
tographic purification of the products, Merck silica Gel
60 (230—400 Mesh) was used. The reagent grade
chemicals were purchased from the commercial sources
and further purified before use.
5a—5m were confirmed by IR, H NMR, 13C NMR,
1
FAB-Mass and chemical analysis. All the final synthe-
*
E-mail: pushkalsamadhiya@rediffmail.com
Received September 29, 2010; revised October 29, 2010; accepted December 3, 2010.
Project supported by the
Chin. J. Chem. 2011, 29, 1001— 1010
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1001

Samadhiya et al.
FULL PAPER
Scheme 1
Synthesis of N-(2-chloroethyl)-2-aminothiazole (1)
1
Yield 62%, m.p. 67—69 ℃; H NMR (CDCl3, 300
MHz) δ: 4.36 (t, J＝7.60 Hz, 2H, CH2Cl), 3.76—3.83
(m, 2H, NCH2), 7.22 (d, J＝4.68 Hz, 1H, C4H of thia-
zole), 7.72 (d, J＝4.68 Hz, 1H, C5H of thiazole), 7.90 (t,
J＝4.30 Hz, 1H, NH); 13C NMR (CDCl3, 75 MHz) δ:
45.8 (CH2Cl), 52.6 (NCH2), 109.8 (C5 of thiazole),
139.2 (C4 of thiazole), 169.2 (C2 of thiazole); IR (KBr)
v: 758 (C—Cl), 882 (C—S), 1349 (N—CH2), 1562 (C
－1
＝C), 2887, ＋3046 (CH), 3480 (NH) cm ; Mass (FAB)
m/z: 163 (M ). Anal. calcd for C5H7N2SCl: C 36.92, H
4.33, N 17.22; found C 36.90, H 4.31, N 17.19.
Synthesis of compound 2 by conventional method
A mixture of compound 1 and hydrazine hydrate (1∶1,
molar ratio) was dissolved in methanol at room tem-
perature. The reaction mixture was continuously stirred
on a magnetic stirrer for about 5.00 h. The product was
filtered and purified over a column chromatography.
The purified product was recrystallized from ethanol at
room temperature to yield compound 2.
Synthesis
of
N-{2-(hydrazino)-ethyl}-2-ami-
1
nothiazole (2) Yield 70%, m.p. 51—53 ℃; H NMR
(CDCl3, 300 MHz) δ: 3.26—3.33 (m, 2H, CH2NH),
3.75—3.83 (m, 2H, NCH2), 5.56 (s, 2H, NH2), 6.86 (d,
J＝4.90 Hz, 1H, C5H of thiazole), 7.28 (d, J＝4.90 Hz,
1H, C4H of thiazole), 7.73 (t, J＝4.70 Hz, 1H, NH),
13
Ar＝Ar1
Comp.
3h—5h
3i—5i
Ar＝Ar1
7.86 (t, J＝4.35 Hz, 1H, NH); C NMR (CDCl3, 75
Comp.
3a—5a
3b—5b
3c—5c
3d—5d
3e—5e
3f—5f
3g—5g
MHz) δ: 49.6 (CH2NH), 54.8 (NCH2), 114.5 (C5 of
thiazole), 142.6 (C4 of thiazole), 173.1 (C2 of thiazole);
IR (KBr) v: 870 (C—S), 1228 (C—N), 3372 (NH), 3434
C6H5
4-NO2C6H4
3-NO2C6H4
2-NO2C6H4
4-CH3OC6H4
4-CH3C6H4
4-HOC6H4
4-ClC6H4
3-ClC6H4
2-ClC6H4
4-BrC6H4
3-BrC6H4
2-BrC6H4
＋
－1
3j—5j
3k—5k
3l—5l
(NH2) cm ; Mass (FAB) m/z: 158 (M ). Anal. calcd
for C5H10N4S: C 37.95, H 6.37, N 20.26; found C 37.92,
H 6.34, N 20.25.
3m—5m
General procedure for the synthesis of compounds
3a—3m by conventional method
A mixture of compound 2 and substituted benzalde-
hydes (1∶1, molar ratio) was dissolved in methanol at
room temperature and allowed to react. The reaction
mixture was first continuously stirred on a magnetic
stirrer for about 2.30—3.30 h, then kept on a steam bath
for about 1.45—2.30 h. The products were cooled and
filtered, the products were purified over a column
chromatography and recrystallized from ethanol at room
temperature to yield compounds 3a—3m.
General method for the synthesis of compounds 1, 2,
3a— 3m and 4a— 4m by microwave method
A solid supported mixture of compounds (1∶1,
molar ratio) was mixed thoroughly in open glass vessel
and subjected to the microwave irradiation at low power
setting (25%, 200 W) for 2.40—4.15 min, then allowed
to cool. The products were purified over a column chro-
matography and recrystallized from ethanol at room
temperature to yield compounds 1, 2, 3a—3m and
4a—4m.
Synthesis of N-{2-(benzylidenehydrazino)-ethyl}-
2-aminothiazole (3a) Yield 60%, m.p. 60—63 ℃; 1H
NMR (CDCl3, 300 MHz) δ: 3.22—3.34 (m, 2H,
CH2NH), 3.72—3.80 (m, 2H, NCH2), 6.62 (d, J＝4.90
Hz, 1H, C5H of thiazole), 7.24 (d, J＝4.90 Hz, 1H, C4H
of thiazole), 7.68 (t, J＝4.75 Hz, 1H, NH), 7.88 (t, J＝
4.35 Hz, 1H, NH), 7.96 (s, 1H, N＝CH), 6.30—7.31 (m,
5H, ArH); 13C NMR (CDCl3, 75 MHz) δ: 47.7
(CH2NH), 52.6 (NCH2), 113.9 (C5 of thiazole), 139.5
(C4 of thiazole), 151.5 (N＝CH), 169.8 (C2 of thiazole),
124.7, 125.8, 127.8, 129.7, 131.8, 137.9 (6C, Ar); IR
Synthesis of the compound 1 by conventional method
A mixture of 2-aminothiazole and 1-bromo-2-
chloroethane (1 ∶1, molar ratio) was dissolved in
methanol at room temperature. The reaction mixture
was continuously stirred on a magnetic stirrer for about
6.15 h. The product was filtered and purified over a
column chromatography. The purified product was re-
crystallized from ethanol at room temperature to yield
compound 1.
－1
(KBr) v: 155＋2 (N＝CH), 3360 (NH) cm ; Mass (FAB)
m/z: 246 (M ). Anal. calcd for C12H14N4S: C 58.51, H
1002
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Chin. J. Chem. 2011, 29, 1001— 1010

Synthesis and Biological Study of Some 4-oxo-Thiazolidine Derivatives of 2-Aminothiazole
＋
－1
5.72, N 22.74; found C 58.45, H 5.67, N 22.70.
(NH) cm ; Mass (FAB) m/z: 325 (M ). Anal. calcd for
C12H13N4SBr: C 44.31, H 4.02, N 17.22; found C 44.27,
H 3.95, N 17.15.
Synthesis of N-{2-(4-chlorobenzylidenehydra-
zino)-ethyl}-2-aminothiazole (3b) Yield 64%, m.p.
1
80—83 ℃; H NMR (CDCl3, 300 MHz) δ: 3.25—3.32
Synthesis of N-{2-(3-bromobenzylidenehydrazi-
no)-ethyl}-2-aminothiazole (3f) Yield 65%, m.p.
(m, 2H, CH2NH), 3.83—3.89 (m, 2H, NCH2), 7.32 (d,
J＝4.95 Hz, 1H, C5H of thiazole), 7.44 (d, J＝4.95 Hz,
1H, C4H of thiazole), 7.77 (t, J＝4.70 Hz, 1H, NH),
7.95 (t, J＝4.38 Hz, 1H, NH), 8.05 (s, 1H, N＝CH),
6.40—7.88 (m, 4H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 48.5 (CH2NH), 57.5 (NCH2), 116.5 (C5 of thiazole),
144.5 (C4 of thiazole), 158 (N＝CH), 172.0 (C2 of thia-
zole), 125.4, 128.8, 129.5, 130.9, 134.8, 140.2 (6C, Ar);
IR －(KBr) v: 3371 (NH), 1575 (N＝CH), 749 (C—Cl)
1
76—78 ℃; H NMR (CDCl3, 300 MHz) δ: 3.34—3.40
(m, 2H, CH2NH), 3.80—3.88 (m, 2H, NCH2), 7.17 (d,
J＝5.20 Hz, 1H, C5H of thiazole), 7.32 (d, J＝5.20 Hz,
1H, C4H of thiazole), 7.55 (t, J＝4.82 Hz, 1H, NH),
7.83 (t, J＝4.35 Hz, 1H, NH), 7.95 (s, 1H, N＝CH),
6.53—7.97 (m, 4H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 49.8 (CH2NH), 57.4 (NCH2), 112.9 (C5 of thiazole),
141.9 (C4 of thiazole), 157.6 (N＝CH), 172.6 (C2 of
thiazole), 124.5, 126.9, 129.8, 131.8, 137.7, 141.7 (6C,
Ar); IR (KBr) v: 652 (C—Br), 1573 (N＝CH), 3376
＋
1
cm ; Mass (FAB) m/z: 281 (M ). Anal. calcd for
C12H13N4SCl: C 51.33, H 4.66, N 19.95; found C 51.30,
H 4.61, N 19.93.
＋
－1
(NH) cm ; Mass (FAB) m/z: 325 (M ). Anal. calcd for
C12H13N4SBr: C 44.31, H 4.02, N 17.22; found C 44.25,
H 4.00, N 17.18.
Synthesis of N-{2-(3-chlorobenzylidenehydra-
zino)-ethyl}-2-aminothiazole (3c) Yield 67%, m.p.
1
80—81 ℃; H NMR (CDCl3, 300 MHz) δ: 3.30—3.36
Synthesis of N-{2-(2-bromobenzylidenehydrazi-
no)-ethyl}-2-aminothiazole (3g) Yield 63%, m.p.
(m, 2H, CH2NH), 3.79—3.85 (m, 2H, NCH2), 7.18 (d,
J＝4.94 Hz, 1H, C5H of thiazole), 7.27 (d, J＝4.94 Hz,
1H, C4H of thiazole), 7.82 (t, J＝4.77 Hz, 1H, NH),
7.94 (t, J＝4.35 Hz, 1H, NH), 7.99 (s, 1H, N＝CH),
6.43—7.65 (m, 4H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 48.5 (CH2NH), 57.5 (NCH2), 113.6 (C5 of thiazole),
141.6 (C4 of thiazole), 157.5 (N＝CH), 172.2 (C2 of
thiazole), 126.3, 128.9, 130.8, 132.8 136.9, 137.8 (6C,
Ar); IR (KBr) v: 755 (C—Cl), 1568 (N＝CH), 3371
1
79—81 ℃; H NMR (CDCl3, 300 MHz) δ: 3.33—3.41
(m, 2H, CH2NH), 3.90—3.97 (m, 2H, NCH2), 7.16 (d,
J＝5.10 Hz, 1H, C5H of thiazole), 7.38 (d, J＝5.10 Hz,
1H, C4H of thiazole), 6.69 (t, J＝4.83 Hz, 1H, NH),
7.80 (t, J＝4.32 Hz, 1H, NH), 8.02 (s, 1H, N＝CH),
6.62—7.93 (m, 4H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 48.1 (CH2NH), 59.4 (NCH2), 111.7 (C5 of thiazole),
140.9 (C4 of thiazole), 159 (N＝CH), 171.2 (C2 of thia-
zol－e), 126.8, 128.5, 129.5, 131.7, 133.9, 145.8 (6C, Ar)
＋
－1
(NH) cm ; Mass (FAB) m/z: 281 (M ). Anal. calcd for
C12H13N4SCl: C 51.33, H 4.66, N 19.95; found C 51.32,
H 4.60, N 19.90.
1
cm ; IR (KBr) v: 642 (C—Br), 1＋564 (N＝CH), 3379
(NH); Mass (FAB) m/z: 325 (M ). Anal. calcd for
C12H13N4SBr: C 44.31, H 4.02, N 17.22; found C 44.27,
H 3.92, N 17.18.
Synthesis of N-{2-(2-chlorobenzylidenehydrazi-
no)-ethyl}-2-aminothiazole (3d) Yield 65%, m.p.
1
82—84 ℃; H NMR (CDCl3, 300 MHz) δ: 3.35—3.42
Synthesis of N-{2-(4-nitrobenzylidenehydrazi-
no)-ethyl}-2-aminothiazole (3h) Yield 64%, m.p.
(m, 2H, CH2NH), 3.80—3.88 (m, 2H, NCH2), 7.22 (d,
J＝5.05 Hz, 1H, C5H of thiazole), 7.38 (d, J＝5.05 Hz,
1H, C4H of thiazole), 7.78 (t, J＝4.78 Hz, 1H, NH),
7.87 (t, J＝4.36 Hz, 1H, NH), 7.95 (s, 1H, N＝CH),
6.68—7.38 (m, 4H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 49.5 (CH2NH), 57.8 (NCH2), 112.5 (C5 of thiazole),
141.8 (C4 of thiazole), 159.5 (N＝CH), 171.3 (C2 of
thiazole), 126.6, 128.7, 129.5, 130.5, 132.8, 139.9 (6C,
Ar); IR (KBr) v: 748 (C—Cl), 1571 (N＝CH), 3386
1
85—87 ℃; H NMR (CDCl3, 300 MHz) δ: 3.41—3.47
(m, 2H, CH2NH), 3.76—3.84 (m, 2H, NCH2), 7.24 (d,
J＝5.16 Hz, 1H, C5H of thiazole), 7.40 (d, J＝5.16 Hz,
1H, C4H of thiazole), 7.61 (t, J＝4.85 Hz, 1H, NH),
7.70 (t, J＝4.32 Hz, 1H, NH), 8.05 (s, 1H, N＝CH),
7.02—8.21 (m, 4H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 48.3 (CH2NH), 56.3 (NCH2), 114.9 (C5 of thiazole),
142.6 (C4 of thiazole), 157.4 (N＝CH), 172.9 (C2 of
thiazole), 122.6, 124.9, 128.8, 129.8, 138.8, 147.9 (6C,
Ar); IR (KBr) v: 842 (C—N), 1552 (N＝O), 1588 (N＋＝
＋
－1
(NH) cm ; Mass (FAB) m/z: 281 (M ). Anal. calcd for
C12H13N4SCl: C 51.33, H 4.66, N 19.95; found C 51.27,
H 4.63, N 19.92.
－1
CH), 3388 (NH) cm ; Mass (FAB) m/z: 291 (M ).
Synthesis of N-{2-(4-bromobenzylidenehydrazi-
Anal. calcd for C12H13N5SO2: C 49.47, H 4.49, N 24.03;
found C 49.42, H 4.44, N 24.00.
no)ethyl}-2-aminothiazole (3e)
Yield 66%, m.p.
1
78—80 ℃; H NMR (CDCl3, 300 MHz) δ: 3.32—3.40
(m, 2H, CH2NH), 3.82—3.91 (m, 2H, NCH2), 7.14 (d,
J＝5.15 Hz, 1H, C5H of thiazole), 7.29 (d, J＝5.15 Hz,
1H, C4H of thiazole), 7.69 (t, J＝4.70 Hz, 1H, NH),
7.88 (t, J＝4.36 Hz, 1H, NH), 7.98 (s, 1H, N＝CH),
6.49—7.99 (m, 4H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 48.7 (CH2NH), 56.8 (NCH2), 114.7 (C5 of thiazole),
142.9 (C4 of thiazole), 155.6 (N＝CH), 171.5 (C2 of
thiazole), 123.8, 127.5, 129.8, 132.8, 133.9, 137.7 (6C,
Ar); IR (KBr) v: 630 (C—Br), 1545 (N＝CH), 3382
Synthesis of N-{2-(3-nitrobenzylidenehydrazino)-
ethyl}-2-aminothiazole (3i) Yield 62%, m.p. 82—83
1
℃; H NMR (CDCl3, 300 MHz) δ: 3.36—3.42 (m, 2H,
CH2NH), 3.82—3.92 (m, 2H, NCH2), 7.24 (d, J＝5.05
Hz, 1H, C5H of thiazole), 7.36 (d, J＝5.05 Hz, 1H, C4H
of thiazole), 6.68 (t, J＝4.80 Hz, 1H, NH), 7.77 (t, J＝
4.35 Hz, 1H, NH), 7.98 (s, 1H, N＝CH), 7.09—8.16 (m,
4H, ArH); 13C NMR (CDCl3, 75 MHz) δ: 45.9
(CH2NH), 51.6 (NCH2), 113.6 (C5 of thiazole), 141.2
(C4 of thiazole), 156.7 (N＝CH), 171.8 (C2 of thiazole),
Chin. J. Chem. 2011, 29, 1001— 1010
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122.8, 125.6, 128.9, 133.7, 137.5, 151.5 (6C, Ar); IR
75 MHz) δ: 48.8 (CH2NH), 59.1 (NCH2), 113.7 (C5 of
thiazole), 140.6 (C4 of thiazole), 158.7 (N＝CH), 172.1
(C2 of thiazole), 116.7, 118.9, 126.9, 129.8, 131.7, 154.8
(6C, Ar);－IR (KBr) v: 1569 (N＝CH),＋3380 (NH), 3478
(KBr) v: 33－81 (NH), 1538 (N＝O), 1578＋(N＝CH), 854
1
(C—N) cm ; Mass (FAB) m/z: 291 (M ). Anal. calcd
for C12H13N5SO2: C 49.47, H 4.49, N 24.03; found C
49.40, H 4.42, N 23.96.
1
(OH) cm ; Mass (FAB) m/z: 262 (M ). Anal. calcd for
Synthesis of N-{2-(2-nitrobenzylidenehydrazino)-
ethyl}-2-aminothiazole (3j) Yield 61%, m.p. 86—88
C12H14N4SO: C 54.94, H 5.37, N 21.35; found C 54.90,
H 5.32, N 21.31.
1
℃; H NMR (CDCl3, 300 MHz) δ: 3.35—3.41 (m, 2H,
General conventional methods for the synthesis of
compounds 4a— 4m
CH2N), 3.89—3.94 (m, 2H, NCH2), 7.26 (d, J＝4.95 Hz,
1H, C5H of thiazole), 7.35 (d, J＝4.95 Hz, 1H, C4H of
thiazole), 7.64 (t, J＝4.72 Hz, 1H, NH), 7.72 (t, J＝4.30
Hz, 1H, NH), 8.07 (s, 1H, N＝CH), 7.16—8.29 (m, 4H,
ArH); 13C NMR (CDCl3, 75 MHz) δ: 47.3 (CH2N), 55.3
(NCH2), 113.7 (C5 of thiazole), 141.8 (C4 of thiazole),
155.9 (N＝CH), 171.5 (C2 of thiazole), 122.8, 125.6,
127.8, 133.7, 137.9, 149.6 (6C, Ar); IR (KBr) v: 842
A mixture of compounds 3a—3m and thioglycolic
acid (1∶1, molar ratio) dissolved in methanol was al-
lowed to react in the presence of catalytic amount of
ZnCl2. The reaction mixture was first continuous stirred
on a magnetic stirrer for about 2.00—2.45 h, then kept
on steam bath for about 2.30—3.45 h at 80—90 ℃.
The products were cooled and filtered at room tempera-
ture. The filtered products were purified over column
chromatography and recrystallized from ethanol at room
temperature to yield compounds 4a—4m.
－1
(C—N), 1548 (N＝O), 1579 (N＝CH), 3352 (NH) cm ;
＋
Mass (FAB) m/z: 291 (M ). Anal. calcd for
C12H13N5SO2: C 49.47, H 4.49, N 24.03; found C 49.43,
H 4.49, N 23.93.
Synthesis of N-[2-{-2-(phenyl)-4-oxo-1,3-thiazoli-
dine}-iminoethyl]-2-aminothiazole (4a) Yield 64%,
m.p. 70—73 ℃; 1H NMR (CDCl3, 300 MHz) δ: 3.29 (s,
2H, SCH2), 4.52 (s, 1H, NCH), 6.96 (d, J＝5.15 Hz, 1H,
C5H of thiazole), 7.25 (d, J＝5.15 Hz, 1H, C4H of thia-
zole), 6.34—7.49 (m, 4H, ArH); 13C NMR (CDCl3, 75
MHz) δ: 35.6 (CH2S), 60.5 (NCH), 108.8 (C5 of thia-
zole), 138.1 (C4 of thiazole), 170.6 (C2 of thiazole),
172.6 (CO, cyclic), 125.8, 126.6, 127.5, 128.7, 130.6,
137.5 (6C, Ar); IR (KBr) v: 672 (C—S—C), 1320
Synthesis of N-{2-(4-methoxybenzylidenehydrazi-
no)-ethyl}-2-aminothiazole (3k) Yield 60%, m.p.
1
71—73 ℃; H NMR (CDCl3, 300 MHz) δ: 3.28—3.36
(m, 2H, CH2NH), 3.59 (s, 3H, OCH3), 3.78—3.86 (m,
2H, NCH2), 7.19 (d, J＝5.16 Hz, 1H, C5H of thiazole),
7.30 (d, J＝5.16 Hz, 1H, C4H of thiazole), 7.78 (t, J＝
4.68 Hz, 1H, NH), 7.88 (t, J＝4.37 Hz, 1H, NH), 7.92 (s,
1H, N＝CH), 6.64—7.78 (m, 4H, ArH); 13C NMR
(CDCl3, 75 MHz) δ: 47.6 (CH2NH), 53.7 (OCH3), 55.6
(NCH2), 110.2 (C5 of thiazole), 138.8 (C4 of thiazole),
155.8 (N＝CH), 169.8 (C2 of thiazole), 114.7, 117.9,
126.8, 128.9, 131.6, 159.9 (6C, Ar); IR (KBr) v: 1574
－1
(C—N), 1732 (CO cyclic), 2928 (S—CH2) cm ; Mass
(FAB) m/z: 320 (M＋). Anal. calcd for C14H16N4S2O: C
52.47, H 5.03, N 17.48; found C 52.40, H 5.00, N 17.43.
Synthesis of N-[2-{2-(4-chlorophenyl)-4-oxo-1,3-
－1
(N＝CH), 2952 (OCH3), 3369 (NH) cm ; Mass (FAB)
m/z: 276 (M＋). Anal. calcd for C13H16N4SO: C 56.49, H
5.83, N 20.27; found C 56.42, H 5.80, N 20.22.
thiazolidine-imino}-ethyl-2-aminothiazole
(4b)
1
Yield 65%, m.p. 88—90 ℃; H NMR (CDCl3, 300
MHz) δ: 3.58 (s, 2H, SCH2), 4.86 (s, 1H, NCH), 6.90 (d,
J＝5.10 Hz, 1H, C5H of thiazole), 7.38 (d, J＝5.10 Hz,
1H, C4H of thiazole), 6.37—7.74 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 40.5 (CH2S), 64.8 (NCH),
113.8 (C5 of thiazole), 141.7 (C4 of thiazole), 172.5 (C2
of thiazole), 174.5 (CO cyclic), 126.7, 127.8, 128.6,
129.7, 130.8, 138.9 (6C, Ar); IR (KBr) v: 676 (C—S—
C), 753 (C—Cl), 1328 (C—N), 1746 (CO cycl＋ic), 2930
Synthesis of N-{2-(4-methylbenzylidenehydrazi-
no)-ethyl}-2-aminothiazole (3l)
Yield 61%, m.p.
66—68 ℃; 1H NMR (CDCl3, 300 MHz) δ: 2.50 (s, 3H,
CH3), 3.24—3.30 (m, 2H, CH2NH), 3.72—3.81 (m, 2H,
NCH2), 7.04 (d, J＝5.20 Hz, 1H, C5H of thiazole), 7.19
(d, J＝5.20 Hz, 1H, C4H of thiazole), 7.68 (t, J＝4.70
Hz, 1H, NH), 7.74 (t, J＝4.30 Hz, 1H, NH), 7.80 (s, 1H,
N＝CH), 6.49—7.59 (m, 4H, ArH); 13C NMR (CDCl3,
75 MHz) δ: 25.9 (CH3), 45.3 (CH2NH), 54.7 (NCH2),
108.5 (C5 of thiazole), 139.2 (C4 of thiazole), 154.7 (N
＝CH), 170.2 (C2 of thiazole), 125.8, 127.8, 129.8,
131.7, 134.9, 139.8 (6C, Ar); IR－(KBr) v: 1562 (N＝
－1
(S—CH2) cm ; Mass (FAB) m/z: 355 (M ). Anal.
calcd for C14H15N4S2OCl: C 47.38, H 4.26, N 15.78;
found C 47.33, H 4.24, N 15.75.
1
Synthesis of N-[2-{2-(3-chlorophenyl)-4-oxo-1,3-
CH), 2937 (CH3), 3352 (NH) cm ; Mass (FAB) m/z:
206 (M＋). Anal. calcd for C13H16N4S: C 59.97, H 6.19,
N 21.51; found C 59.92, H 6.14, N 21.50.
thiazolidine-imino}-ethyl-2-aminothiazole
(4c)
1
Yield 65%, m.p. 91—93 ℃; H NMR (CDCl3, 300
MHz) δ: 3.61 (s, 2H, SCH2), 4.82 (s, 1H, NCH), 6.92 (d,
J＝5.05 Hz, 1H, C5H of thiazole), 7.36 (d, J＝5.05 Hz,
1H, C4H of thiazole), 6.38—7.72 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 38.6 (CH2S), 64.2 (NCH),
113.6 (C5 of thiazole), 142.4 (C4 of thiazole), 171.6 (C2
of thiazole), 175.8 (CO cyclic), 125.8, 126.6, 127.7,
128.8, 129.8, 137.9 (6C, Ar); IR (KBr) v: 672 (C—S—
C), 743 (C—Cl), 1325 (C—N), 1748 (CO cyclic), 2936
Synthesis of N-{2-(4-hydroxybenzylidenehydrazi-
no)-ethyl}-2-aminothiazole (3m) Yield 62%, m.p.
75—78 ℃; 1H NMR (CDCl3, 300 MHz) δ: 4.12 (s, 1H,
OH), 3.37—3.44 (m, 2H, CH2NH), 3.91—3.99 (m, 2H,
NCH2), 7.16 (d, J＝5.15 Hz, 1H, C5H of thiazole), 7.36
(d, J＝5.15 Hz, 1H, C4H of thiazole), 7.72 (t, J＝4.78
Hz, 1H, NH), 7.84 (t, J＝4.32 Hz, 1H, NH), 8.01 (s, 1H,
N＝CH), 6.52—7.69 (m, 4H, ArH); 13C NMR (CDCl3,
1004
www.cjc.wiley-vch.de
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 1001— 1010

Synthesis and Biological Study of Some 4-oxo-Thiazolidine Derivatives of 2-Aminothiazole
＋
－1
(S—CH2) cm ; Mass (FAB) m/z: 355 (M ). Anal.
calcd for C14H15N4S2OCl: C 47.38, H 4.26, N 15.78;
found C 47.34, H 4.24, N 15.72.
14.03; found C 42.01, H 3.70, N 13.9.
Synthesis of N-[2-{2-(4-nitrophenyl)-4-oxo-1,3-
thiazolidine}-iminoethyl]-2-aminothiazole (4h)
1
Synthesis of N-[2-{2-(2-chlorophenyl)-4-oxo-1,3-
Yield 64%, m.p. 83—85 ℃; H NMR (CDCl3, 300
MHz) δ: 3.48 (s, 2H, SCH2), 4.78 (s, 1H, NCH), 6.82 (d,
J＝4.90 Hz, 1H, C5H of thiazole), 7.40 (d, J＝4.90 Hz,
1H, C4H of thiazole), 6.98—8.34 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 41.7 (CH2S), 62.5 (NCH),
113.5 (C5 of thiazole), 139.9 (C4 of thiazole), 169.8 (C2
of thiazole), 173.7 (CO cyclic), 125.7, 126.6, 127.7,
128.7, 129.9, 138.4 (6C, Ar); IR (KBr) v: 666 (C—S—
C), 840 (C—NO), 1334 (C—N), 1518 (NO2), 1746 (CO
thiazolidine}-iminoethyl]-2-aminothiazole
(4d)
1
Yield 66%, m.p. 85—87 ℃; H NMR (CDCl3, 300
MHz) δ: 3.65 (s, 2H, SCH2), 4.89 (s, 1H, NCH), 6.95 (d,
J＝5.05 Hz, 1H, C5H of thiazole), 7.42 (d, J＝5.05 Hz,
1H, C4H of thiazole), 6.32—7.66 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 40.2 (CH2S), 64.2 (NCH),
113.8 (C5 of thiazole), 142.4 (C4 of thiazole), 172.8 (C2
of thiazole), 176.6 (CO cyclic), 126.6, 127.8, 128.7,
129.8, 130.9, 139.6 (6C, Ar); IR (KBr) v: 672 (C—S—
C), 744 (C—Cl), 1327 (C—N), 1755 (CO cycl＋ic), 2938
－1
cyclic), 2938 (S—CH2) cm ; Mass (FAB) m/z: 365
(M＋). Anal. calcd for C14H15N5S2O3: C 46.01, H 4.13, N
19.16; found C 45.91, H 4.10, N 19.12.
－1
(S—CH2) cm ; Mass (FAB) m/z: 355 (M ). Anal.
calcd for C14H15N4S2OCl: C 47.38, H 4.26, N 15.78;
found C 47.33, H 4.20, N 15.71.
Synthesis of N-[2-{2-(3-nitrophenyl)-4-oxo-1,3-
thiazolidine}-iminoethyl]-2-aminothiazole
(4i)
1
Synthesis of N-[2-{2-(4-bromophenyl)-4-oxo-1,3-
thiazolidine}-iminoethyl]-2-aminothiazole (4e) Yield
Yield 63%, m.p. 80—82 ℃; H NMR (CDCl3, 300
MHz) δ: 3.47 (s, 2H, SCH2), 4.86 (s, 1H, NCH), 6.88 (d,
J＝5.00 Hz, 1H, C5H of thiazole), 7.37 (d, J＝5.00 Hz,
1H, C4H of thiazole), 7.08—8.27 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 39.9 (CH2S), 62.5 (NCH),
111.7 (C5 of thiazole), 140.8 (C4 of thiazole), 169.5 (C2
of thiazole), 172.8 (CO cyclic), 126.8, 127.8, 128.7,
129.6, 131.5, 139.9 (6C, Ar); IR (KBr) v: 670
(C—S—C), 864 (C—NO), 1322 (C—N), 1531 (NO2),
1
60%, m.p. 84—86 ℃; H NMR (CDCl3, 300 MHz) δ:
3.49 (s, 2H, SCH2), 4.81 (s, 1H, NCH), 6.82 (d, J＝5.00
Hz, 1H, C5H of thiazole), 7.39 (d, J＝5.00 Hz, 1H, C4H
of thiazole), 6.41—7.99 (m, 4H, ArH); 13C NMR
(CDCl3, 75 MHz) δ: 42.4 (CH2S), 62.1 (NCH), 113.8
(C5 of thiazole), 141.2 (C4 of thiazole), 172.8 (C2 of
thiazole), 176.6 (CO cyclic), 126.7, 127.9, 128.8, 129.7,
130.9, 139.8 (6C, Ar); IR (KBr) v: 678 (C—S—C), 744
(C—Br), 1327 (C—N), 1752 (CO cycli＋c), 2938
－1
1742 (CO cyclic), 2937 (S—CH2) cm ; Mass (FAB)
m/z: 365 (M＋). Anal. calcd for C14H15N5S2O3: C 46.01,
H 4.13, N 19.16; found C 45.94, H 4.08, N 19.12.
Synthesis of N-[2-{2-(2-nitrophenyl)-4-oxo-1,3-
－1
(S—CH2) cm ; Mass (FAB) m/z: 399 (M ). Anal.
calcd for C14H15N4S2OBr: C 42.10, H 3.78, N 14.03;
found C 42.05, H 3.72, N 14.00.
thiazolidine}-iminoethyl]-2-aminothiazole
(4j)
1
Synthesis of N-[2-{2-(3-bromophenyl)-4-oxo-1,3-
Yield 61%, m.p. 78—81 ℃; H NMR (CDCl3, 300
MHz) δ: 3.48 (s, 2H, SCH2), 4.81 (s, 1H, NCH), 6.87 (d,
J＝5.05 Hz, 1H, C5H of thiazole), 7.38 (d, J＝5.05 Hz,
1H, C4H of thiazole), 7.12—8.38 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 38.4 (CH2S), 62.8 (NCH),
111.7 (C5 of thiazole), 139.5 (C4 of thiazole), 170.8 (C2
of thiazole), 171.7 (CO cyclic), 126.8, 127.9, 128.7,
128.8, 129.5, 138.8 (6C, Ar); IR (KBr) v: 678
(C—S—C), 845 (C—NO), 1332 (C—N), 1537 (NO2),
thiazolidine}-iminoethyl]-2-aminothiazole
(4f)
1
Yield 64%, m.p. 85—87 ℃; H NMR (CDCl3, 300
MHz) δ: 3.47 (s, 2H, SCH2), 4.85 (s, 1H, NCH), 6.88 (d,
J＝4.95 Hz, 1H, C5H of thiazole), 7.43 (d, J＝4.95 Hz,
1H, C4H of thiazole), 6.45—8.09 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 41.7 (CH2S), 63.6 (NCH),
114.4 (C5 of thiazole), 141.3 (C4 of thiazole), 171.5 (C2
of thiazole), 174.4 (CO cyclic), 126.8, 127.8, 128.5,
128.7, 129.8, 138.7 (6C, Ar); IR (KBr) v: 672
(C—S—C), 752 (C—Br－), 1337 (C—N), 1748 (CO cy-
－1
1745 (CO cyclic), 2921 (S—CH2) cm ; Mass (FAB)
m/z: 365 (M＋). Anal. calcd for C14H15N5S2O3: C 46.01,
H 4.13, N 19.16; found C 45.95, H 4.08, N 19.11.
Synthesis of N-[2-{2-(4-methoxyphenyl)-4-oxo-
＋
1
clic), 2987 (S—CH2) cm ; Mass (FAB) m/z: 399 (M ).
Anal. calcd for C14H15N4S2OBr: C 42.10, H 3.78, N
14.03; found C 42.07, H 3.74, N 14.01.
1,3-thiazolidine}-iminoethyl]-2-aminothiazole
(4k)
1
Synthesis of N-[2-{2-(2-bromophenyl)-4-oxo-1,3-
Yield 64%, m.p. 76—78 ℃; H NMR (CDCl3, 300
MHz) δ: 3.40 (s, 2H, SCH2), 3.65 (s, 3H, OCH3), 4.78 (s,
1H, NCH), 6.82 (d, J＝4.95 Hz, 1H, C5H of thiazole),
7.38 (d, J＝4.95 Hz, 1H, C4H of thiazole), 6.59—7.47
(m, 4H, ArH); 13C NMR (CDCl3, 75 MHz) δ: 37.4
(CH2S), 60.6 (NCH), 111.7 (C5 of thiazole), 137.9 (C4
of thiazole), 170.2 (C2 of thiazole), 172.7 (CO cyclic),
126.6, 127.8, 128.6, 129.8, 130.6, 138.9 (6C, Ar); IR
(KBr) v: 677 (C—S—C), 1329 (C—N)－, 1739 (CO cy-
thiazolidine}-iminoethyl]-2-aminothiazole
(4g)
1
Yield 66%, m.p. 82—83 ℃; H NMR (CDCl3, 300
MHz) δ: 3.44 (s, 2H, SCH2), 4.81 (s, 1H, NCH), 6.84 (d,
J＝4.90 Hz, 1H, C5H of thiazole), 7.38 (d, J＝4.90 Hz,
1H, C4H of thiazole), 6.47—7.98 (m, 4H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 39.5 (CH2S), 62.3 (NCH),
110.6 (C5 of thiazole), 138.9 (C4 of thiazole), 171.6 (C2
of thiazole), 174.2 (CO cyclic), 126.6, 127.8, 128.7,
129.7, 129.9, 137.9 (6C, Ar); IR (KBr) v: 672
(C—S—C), 744 (C—Br－), 1320 (C—N), 1742 (CO cy-
1
clic), 2922 (S—CH2), 2966 (OCH3) cm ; Mass (FAB)
m/z: 350 (M＋). Anal. calcd for C15H18N4S2O2: C 51.40,
H 5.17, N 15.98; found C 51.30, H 5.14, N 15.95.
Synthesis of N-[2-{2-(4-methylphenyl)-4-oxo-
＋
1
clic), 2935 (S—CH2) cm ; Mass (FAB) m/z: 399 (M ).
Anal. calcd for C14H15N4S2OBr: C 42.10, H 3.78, N
Chin. J. Chem. 2011, 29, 1001— 1010
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1005

Samadhiya et al.
FULL PAPER
1,3-thiazolidine}-iminoethyl]-2-aminothiazole
(4l)
NMR (CDCl3, 300 MHz) δ: 6.48 (s, 1H, C＝CH), 6.90
(d, J＝4.90 Hz, 1H, C5H of thiazole), 7.39 (d, J＝4.90
Hz, 1H, C4H of thiazole), 6.85—7.72 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 114.2 (C5 of thiazole), 141.6
(C4 of thiazole), 145.7 (C＝CH), 149.5 (C＝CH), 170.3
(C2 of thiazole), 125.6, 126.8, 126.7, 127.8, 128.8, 129,
129.9, 130.1, 130.8, 131.7, 138.4, 139.2 (12C, Ar); IR
(KBr) v: 774 (C—Cl), 1625 (C＝CH), 2980 (C＝CH)
1
Yield 63%, m.p. 70—72 ℃; H NMR (CDCl3, 300
MHz) δ: 2.65 (s, 3H, CH3), 3.38 (s, 2H, SCH2), 4.78 (s,
1H, NCH), 6.87 (d, J＝4.90 Hz, 1H, C5H of thiazole),
7.31 (d, J＝4.90 Hz, 1H, C4H of thiazole), 6.49—7.51
(m, 4H, ArH); 13C NMR (CDCl3, 75 MHz) δ: 24.6
(CH3), 33.2 (CH2S), 63.6 (NCH), 111.7 (C5 of thiazole),
138.1 (C4 of thiazole), 167.4 (C2 of thiazole), 169.2 (CO
cyclic), 124.3, 125.7, 127.4, 129.8, 130.7, 131.9, 137.8
(6C, Ar); IR (KBr) v: 670 (C—S—C), 1332 (C—N),
＋
－1
cm ; Mass (FAB) m/z: 477 (M ). Anal. calcd for
C21H18N4S2OCl2: C 52.83, H 3.80, N 11.73; found C
52.80, H 3.78, N 11.70.
－1
1741 (CO cyclic), 2975 (S—CH2), 2970 (CH3) cm ;
＋
Mass (FAB) m/z: 334 (M ). Anal. calcd for
Synthesis of N-[2-{-2-(3-chlorophenyl)-4-oxo-5-(3-
chlorobenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
C15H18N4S2O: C 53.86, H 5.42, N 16.75; found C 53.82,
H 5.36, N 16.72.
1
aminothiazole (5c) Yield 62%, m.p. 86—88 ℃; H
Synthesis of N-[2-{2-(4-hydroxyphenyl)-4-oxo-
1,3-thiazolidine}-iminoethyl]-2-aminothiazole (4m)
NMR (CDCl3, 300 MHz) δ: 6.44 (s, 1H, C＝CH), 7.00
(d, J＝4.95 Hz, 1H, C5H of thiazole), 7.37 (d, J＝4.95
Hz, 1H, C4H of thiazole), 6.71—7.63 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 111.7 (C5 of thiazole), 140.7
(C4 of thiazole), 148.6 (C＝CH), 154.3 (C＝CH), 172.6
(C2 of thiazole), 123.5, 124.8, 125.9, 125.8, 126.2, 126.8,
127.8, 128.9, 129.5, 129.8, 138.7, 140.9 (12C, Ar); IR
(KBr) v: 772 (C—Cl), 1623 (C＝CH), 2980 (C＝CH)
1
Yield 63%, m.p. 80—81 ℃; H NMR (CDCl3, 300
MHz) δ: 3.55 (s, 2H, SCH2), 4.20 (s, 1H, OH), 4.87 (s,
1H, NCH), 6.85 (d, J＝4.90 Hz, 1H, C5H of thiazole),
7.38 (d, J＝4.90 Hz, 1H, C4H of thiazole), 6.47—7.61
(m, 4H, ArH); 13C NMR (CDCl3, 75 MHz) δ: 43.2
(CH2S), 63.8 (NCH), 114.5 (C5 of thiazole), 140.4 (C4
of thiazole), 171.6 (C2 of thiazole), 174.7 (CO, cyclic),
124.7, 125.8, 127.7, 128.9, 129.8, 138.8 (6C, Ar); IR
(KBr) v: 665 (C—S—C), 1329 (C—N－), 1742 (CO cy-
＋
－1
cm ; Mass (FAB) m/z: 477 (M ). Anal. calcd for
C21H18N4S2OCl2: C 52.83, H 3.80, N 11.73; found C
52.81, H 3.74, N 11.67.
1
clic), 2928 (S—CH2), 3480 (OH) cm ; Mass (FAB)
Synthesis of N-[2-{2-(2-chlorophenyl)-4-oxo-5-(2-
chlorobenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
m/z: 336 (M＋). Anal. calcd for C14H16N4S2O2: C 49.98,
1
H 4.79, N 16.65; found C 49.92, H 4.74, N 16.60.
aminothiazole (5d) Yield 64%, m.p. 81—83 ℃; H
NMR (CDCl3, 300 MHz) δ: 6.45 (s, 1H, C＝CH), 6.94
(d, J＝4.90 Hz, 1H, C5H of thiazole), 7.38 (d, J＝4.90
Hz, 1H, C4H of thiazole), 6.71—7.63 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 112.9 (C5 of thiazole), 140.2
(C4 of thiazole), 147.6 (C＝CH), 153.2 (C＝CH), 172.9
(C2 of thiazole), 124.5, 125.8, 126.7, 127.3, 127.8, 128.8,
129.6, 130.8, 131.8, 132.5, 138.6, 141.1 (12C, Ar); IR
(KBr) v: 762 (C—Cl), 1628 (C＝CH), 2987 (C＝CH)
General conventional methods for the synthesis of
compounds 5a— 5m
A mixture of compounds 4a—4m and substituted
benzaldehydes (1∶1 molar, ratio) was dissolved in
methanol in the presence of alkali metal alkoxide
(C2H5ONa) and allowed to react. The reaction mixture
was first continuously stirred on a magnetic stirrer for
about 2.00—2.30 h then kept on steam bath for about
2.45—3.30 h at 80—90 ℃. The products were cooled
and filtered at room temperature. The filtered products
were purified over column chromatography and recrys-
tallized from ethanol at room temperature to yield final
products compounds 5a—5m.
＋
－1
cm ; Mass (FAB) m/z: 477 (M ). Anal. calcd for
C21H18N4S2OCl2: C 52.83, H 3.80, N 11.73; found C
52.78, H 3.74, N 11.67.
Synthesis of N-[2-{2-(4-bromophenyl)-4-oxo-5-(4-
bromobenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
1
aminothiazole (5e) Yield 63%, m.p. 80—82 ℃; H
Synthesis of N-[2-{2-(phenyl)-4-oxo-5-(benzyli-
dene)-1,3-thiazolidine}-iminoethyl]-2-aminothiazole
NMR (CDCl3, 300 MHz) δ: 6.40 (s, 1H, C＝CH), 6.92
(d, J＝5.00 Hz, 1H, C5H of thiazole), 7.36 (d, J＝5.00
Hz, 1H, C4H of thiazole), 6.80—7.77 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 116.9 (C5 of thiazole), 138.7
(C4 of thiazole), 144.8 (C＝CH), 146.8 (C＝CH), 170.5
(C2 of thiazole), 120.8, 121.8, 124.5, 125.7, 126.8, 127－.5,
1
(5a) Yield 66%, m.p. 69—71 ℃; H NMR (CDCl3,
300 MHz) δ: 6.32 (s, 1H, C＝CH), 6.90 (d, J＝4.95 Hz,
1H, C5H of thiazole), 7.35 (d, J＝4.95 Hz, 1H, C4H of
thiazole), 6.71—7.92 (m, 10H, ArH); 13C NMR
(CDCl3, 75 MHz) δ: 110.8 (C5 of thiazole), 139.4 (C4 of
thiazole), 143.8 (C＝CH), 146.9 (C＝CH), 169.8 (C2 of
thiazole), 124.8, 125.8, 126.4, 126.8, 127.8, 127.7,
128.8, 128.7, 129.6, 130.7, 137.8, 138.8 (12C－, Ar); IR
1
127.9, 128.8, 130.4, 131.5, 137.8, 139.9 (12C, Ar) cm ;
IR (KBr) v: 645 (C—Br), 1629 (C＝CH), 2980 (C＝
CH); Mass (FAB) m/z: 566 (M＋ ). Anal. calcd for
C21H18N4S2OBr2: C 44.53, H 3.20, N 9.89; found C
44.50, H 3.18, N 9.87.
1
(KBr) v: 1612 (C＝CH), 2962 (C＝CH) cm ; Mass
(FAB) m/z: 408 (M＋). Anal. calcd for C21H20N4S2O: C
61.73, H 4.93, N 13.71; found C 61.70, H 4.92, N 13.69.
Synthesis of N-[2-{2-(4-chlorophenyl)-4-oxo-5-(4-
chlorobenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
Synthesis of N-[2-{2-(3-bromophenyl)-4-oxo-5-
(3-bromobenzylidene)-1,3-thiazolidine}-iminoethyl]-
2-aminothiazole (5f) Yield 65%, m.p. 78—80 ℃; 1H
NMR (CDCl3, 300 MHz) δ: 6.44 (s, 1H, C＝CH), 6.92
(d, J＝5.15 Hz, 1H, C5H of thiazole), 7.35 (d, J＝5.15
1
aminothiazole (5b) Yield 63%, m.p. 85—87 ℃; H
1006
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Chin. J. Chem. 2011, 29, 1001— 1010

Synthesis and Biological Study of Some 4-oxo-Thiazolidine Derivatives of 2-Aminothiazole
Hz, 1H, C4H of thiazole), 6.78—7.79 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 113.5 (C5 of thiazole), 140.5
(C4 of thiazole), 144.8 (C＝CH), 150.2 (C＝CH), 172.5
(C2 of thiazole), 121.7, 123.8, 125.6, 126.8, 127.7, 128.5,
128.9, 129.7, 131.6, 132.8, 138.6, 140.8 (12C, Ar); IR
(KBr) v: 645 (C—Br), 1628 (C＝CH), 2980 (C＝CH)
NMR (CDCl3, 75 MHz) δ: 112.8 (C5 of thiazole), 140.2
(C4 of thiazole), 144.5 (C＝CH), 148.9 (C＝CH), 171.4
(C2 of thiazole), 123.6, 124.6, 125.7, 126.2, 126.8, 127.8,
128.8, 129.7, 130.4, 132.5, 137.5, 139.9 (12C, Ar); IR
(KBr) v: 860 (C—NO), 1528 (NO2), 1635 (C＝CH),
＋
－1
2978 (C＝CH) cm ; Mass (FAB) m/z: 498 (M ). Anal.
calcd for C21H18N6S2O5: C 50.59, H 3.63, N 16.85;
found C 50.52, H 3.62, N 16.81.
＋
－1
cm ; Mass (FAB) m/z: 566 (M ). Anal. calcd for
C21H18N4S2OBr2: C 44.53, H 3.20, N 9.791; found C
44.45, H 3.12, N 9.81.
Synthesis of N-[2-{2-(4-methoxyphenyl)-4-oxo-5-
(4-methoxybenzylidene)-1,3-thiazolidine}-imino-
ethyl]-2-aminothiazole (5k) Yield 66%, m.p. 78—79
℃; 1H NMR (CDCl3, 300 MHz) δ: 3.68 (s, 3H, OCH3),
6.40 (s, 1H, C＝CH), 6.92 (d, J＝4.85 Hz, 1H, C5H of
thiazole), 7.42 (d, J＝4.85 Hz, 1H, C4H of thiazole),
6.82—7.78 (m, 8H, ArH); 13C NMR (CDCl3, 75 MHz)
δ: 109.4 (C5 of thiazole), 138.7 (C4 of thiazole), 142.1
(C＝CH), 145.5 (C＝CH), 170.3 (C2 of thiazole), 111.7,
112.7, 113.8, 114.2, 124.8, 126.9, 127.5, 128.8, 129.7,
138.6, 154.8, 157.8 (12C, Ar); IR (KB－r) v: 1593 (C＝
Synthesis of N-[2-{2-(2-bromophenyl)-4-oxo-5-
(2-bromobenzylidene)-1,3-thiazolidine}-iminoethyl]-
2-aminothiazole (5g) Yield 64%, m.p. 80—82 ℃; 1H
NMR (CDCl3, 300 MHz) δ: 6.51 (s, 1H, C＝CH), 6.92
(d, J＝5.10 Hz, 1H, C5H of thiazole), 7.35 (d, J＝5.10
Hz, 1H, C4H of thiazole), 6.79—7.75 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 113.1 (C5 of thiazole), 142.5
(C4 of thiazole), 144.4 (C＝CH), 148.3 (C＝CH), 172.3
(C2 of thiazole), 122.5, 124.8, 125.7, 126.7, 127.8, 128.7,
129.8, 130.6, 131.7, 132.8, 137.9, 138.7 (12C, Ar); IR
(KBr) v: 642 (C—Br), 1624 (C＝CH), 2980 (C＝CH)
1
CH), 2982 (C＝CH), 2974 (OCH3) cm ; Mass (FAB)
＋
－1
cm ; Mass (FAB) m/z: 566 (M ). Anal. calcd for
C21H18N4S2OBr2: C 44.53, H 3.20, N 9.791; found C
44.51, H 3.10, N 9.79.
m/z: 468 (M＋). Anal. calcd for C23H24N4S2O3: C 58.95,
H 5.16, N 11.95; found C 58.92, H 5.12, N 11.91.
Synthesis of N-[2-{2-(4-methylphenyl)-4-oxo-5-(4-
methylbenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
Synthesis of N-[2-{2-(4-nitrophenyl)-4-oxo-5-(4-
nitrobenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
1
aminothiazole (5l) Yield 60%, m.p. 74—76 ℃; H
1
aminothiazole (5h) Yield 62%, m.p. 77—79 ℃; H
NMR (CDCl3, 300 MHz) δ: 2.61 (s, 3H, CH3) 6.45 (s,
1H, C＝CH), 6.92 (d, J＝4.85 Hz, 1H, C5H of thiazole),
7.32 (d, J＝4.85 Hz, 1H, C4H of thiazole), 6.79—7.67
(m, 8H, ArH); 13C NMR (CDCl3, 75 MHz) δ: 107.7 (C5
of thiazole), 138.7 (C4 of thiazole), 140.7 (C＝CH),
144.7 (C＝CH), 170.2 (C2 of thiazole), 122.9, 124.8,
125.9, 126.8, 127.9, 128.7, 129.9, 130.5, 133.8, 134.6,
135.9, 137.8 (12C, Ar); IR (KBr) v: 1580 (C＝CH),
NMR (CDCl3, 300 MHz) δ: 6.58 (s, 1H, C＝CH), 7.09
(d, J＝4.95 Hz, 1H, C5H of thiazole), 7.38 (d, J＝4.95
Hz, 1H, C4H of thiazole), 6.89—7.81 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 40.4 (CH2S), 63.2 (NCH),
112.6 (C5 of thiazole), 141.2 (C4 of thiazole), 145.8
(C＝CH), 149.3 (C＝CH), 171.5 (C2 of thiazole), 122.7,
123.8, 125.7, 126.2, 126.8, 127.4, 127.9, 128.5, 129.7,
130.9, 137.7, 138.9 (12C, Ar); IR (KBr) v: 858
(C—NO), 1532 (NO2), 1628 (C＝CH), 2980 (C＝CH)
－1
2972 (C＝CH) 1347 (CH3) cm ; Mass (FAB) m/z: 436
(M＋). Anal. calcd for C23H24N4S2O: C 63.27, H 5.54, N
12.83; found C 63.25, H 5.51, N 12.80.
＋
－1
cm ; Mass (FAB) m/z: 498 (M ). Anal. calcd for
C21H18N6S2O5: C 50.59, H 3.63, N 16.85; found C 50.52,
H 3.61, N 16.81.
Synthesis of N-[2-{2-(4-hydroxyphenyl)-4-oxo-5-
(4-hydroxybenzylidene)-1,3-thiazolidine}-imino-
Synthesis of N-[2-{2-(3-nitrophenyl)-4-oxo-5-
(3-nitrobenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
ethyl]-2-aminothiazole (5m)
Yield 60%, m.p.
86—87 ℃; 1H NMR (CDCl3, 300 MHz) δ: 4.22 (s, 1H,
OH), 6.38 (s, 1H, C＝CH), 6.80 (d, J＝4.90 Hz, 1H,
C5H of thiazole), 7.35 (d, J＝4.90 Hz, 1H, C4H of thia-
zole), 6.71—7.62 (m, 8H, ArH); 13C NMR (CDCl3, 75
MHz) δ: 112.6 (C5 of thiazole), 141.2 (C4 of thiazole),
143.6 (C＝CH), 149.6 (C＝CH), 169.6 (C2 of thiazole),
116.8, 120.9, 122.8, 123.7, 124.8, 126.8, 127.9, 128.7,
130.7, 137.6, 155.6, 157.8 (12C, Ar); IR－(KBr) v: 1628
1
aminothiazole (5i) Yield 63%, m.p. 81—83 ℃; H
NMR (CDCl3, 300 MHz) δ: 6.54 (s, 1H, C＝CH), 7.01
(d, J＝4.95 Hz, 1H, C5H of thiazole), 7.40 (d, J＝4.95
Hz, 1H, C4H of thiazole), 6.87—7.86 (m, 8H, ArH); 13C
NMR (CDCl3, 75 MHz) δ: 112.2 (C5 of thiazole), 140.4
(C4 of thiazole), 144.6 (C＝CH), 149.8 (C＝CH), 172.7
(C2 of thiazole), 120.7, 122.8, 123.8, 125.7, 126.9, 127.8,
128.9, 129.7, 131.8, 132.7, 135.6, 136.8 (12C, Ar); IR
(KBr) v: 852 (C—NO), 1515 (NO2), 1622 (C＝CH),
1
(C＝CH), 2980 (C＝CH), 3618 (OH) cm ; Mass (FAB)
m/z: 440 (M＋). Anal. calcd for C21H20N4S2O3: C 57.25,
＋
－1
2980 (C＝CH) cm ; Mass (FAB) m/z: 498 (M ). Anal.
calcd for C21H18N6S2O5: C 50.59, H 3.63, N 16.85;
found C 50.54, H 3.56, N 16.80.
H 4.57, N 12.71; found C 57.21, H 4.53, N 12.67.
Results and discussion
Synthesis of N-[2-{2-(2-nitrophenyl)-4-oxo-5-(2-
nitrobenzylidene)-1,3-thiazolidine}-iminoethyl]-2-
The reaction of 1-bromo-2-chloroethane with
2-aminothiazole was carried out in methanol to afford a
product compound 1. The spectroscopic analyses of
compound 1 showed absorption peaks for N—CH and
1
aminothiazole (5j) Yield 60%, m.p. 86—88 ℃; H
NMR (CDCl3, 300 MHz) δ: 6.44 (s, 1H, C＝CH), 6.92
(d, J＝4.90 Hz, 1H, C5H of thiazole), 7.36 (d, J＝4.90
Hz, 1H, C4H of thiazole), 6.88—7.81 (m, 8H, ArH); 13C
－1
C—Cl at 1349 and 758 cm in the IR spectrum. The IR
Chin. J. Chem. 2011, 29, 1001— 1010
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1007

Samadhiya et al.
FULL PAPER
Pharmacology
spectrum confirms the formation of compound 1. The
compound 1 on the reaction with hydrazine hydrate with
continuous stirring at room temperature yielded com-
pound 2. In the spectroscopic analyses of compound 2
we found two absorption peaks in IR spectrum for NH
Series of newly synthesized compounds were highly
active against selected microorganisms. The minimal
inhibition values were determined using the filter paper
disc diffusion method and the concentrations have been
used in µg/mL. All the final synthesized compounds
5a—5m have been screened in vitro for their antibacte-
rial activities against B. subtilis, E. coli and S. aureus
and antifungal activities against A. niger, A. flavus and
C. albicans. Standards for antibacterial and antifungal
activities Streptomycin and Griseofulvin were used re-
spectively. Standards were also screened under the
similar conditions for comparison. The antitubercular
activity was screened against the M. tuberculosis. For
the antitubercular activity Isoniazid and Rifampicin
were used as standards and also screened under the
similar conditions.
We have investigated that compounds have a struc-
ture-activity relationship because activity of compounds
varies with substitution. Nitro group containing com-
pounds (5h, 5i and 5j) showed higher activity than
chloro (5c, 5d), or bromo (5e, 5f) group containing
compounds. Chloro and bromo derivatives also have
higher activity than other rested compounds. On the
basis of SAR, it could be concluded that the activity of
compounds depends on electron withdrawing nature of
the substituted groups. The sequence of the activity is as
follows:
－1
and NH2 at 3372 and 3434 cm respectively, while
absorption of C—Cl has disappeared. This clearly indi-
cate that compound 1 gives the substitution reaction
with hydrazine hydrate. This fact was also supported by
1H and 13C NMR spectra because two signals appeared
in the 1H NMR spectrum for NH and NH2 at δ 6.73 and
5.56 respectively. All the facts together were strong
evidence for the synthesis of compound 2. The com-
pound 2 gave the condensation reaction with substituted
benzaldehydes resulting in the production of Schiff
bases N＝CH compounds 3a—3m, which were con-
firmed by IR, 1H NMR and 13C NMR spectra. In the IR
spectra an abs－orption was found in the range of
1
1545—1588 cm while a strong signal appeared in the
1
range of δ 7.80—8.07 and δ 151.5—159.5 in the H
NMR and 13C NMR spectra for N＝CH of compounds
3a—3m, respectively. The facts were also supported by
1
the disappearance of the signal of NH2 in the H NMR
spectra. The compounds 3a—3m on reaction with
equimolar amount of thioglycolic acid in the presence of
ZnCl2 (acted as a catalyst) in the trace amount gave the
cycloaddition reaction and produced a five membered
thiazolidinone ring, compounds 4a—4m. The com-
pounds 4a—4m showed a characteristic absorption for
the－cyclic carbonyl group in the range of 1732—1755
NO Cl Br OH OCH CH
2＞ ＞
＞
＞
＞
3
3
1
1
Antibacterial activity
cm in the IR spectra. The H NMR spectra aroused
our attention and clearly indicate the presence of the
two active methylene protons in the thiazolidine ring in
the range of δ 3.29—3.65. The 13C NMR spectra of
compounds 4a—4m also supported the fact that cyclic
carbonyl group was present and a signal appeared in the
range of δ 176.6—169.2. These facts were also sup-
ported by the two evidences that are (a) disappearance
of N＝CH proton and (b) appearance of N—CH proton
The above synthesized compounds were screened
against some selected bacteria and examined for the
inhibition of growth of the organism. The concentra-
tions of the compounds were given in µg/mL. The di-
ameters of the inhibition zones in mm are given in Table
2.
Antifungal activity
1
The above synthesized compounds were screened
against selected fungi, and their determined minimal
inhibition zones in mm and were presented in Table 2.
Concentrations of compounds were given in µg/mL.
in the range of δ 4.52—4.89 in the H NMR spectra of
compounds 4a—4m. The compounds 4a—4m under-
went the Knoevenagel condensation reaction with sub-
stituted benzaldehydes in the presence of alkali metal
alkoxide (C2H5ONa) to afford the compounds 5a—5m.
Antitubercular activity
1
In the H NMR spectra of the compounds 5a—5m, we
The above synthesized compounds were screened
against M. tuberculosis (H37Rv strain) using L. J. me-
dium (Conventional) method at 25, 50 µg/mL and lower
concentrations. The results are shown in Table 3. Anti-
tubercular drugs Isoniazid and Rifampicin (MIC range
0.2—4.5 µg/mL) were taken as standards.
found the disappearance of two methylene protons of
compounds 5a—5m and an appearance of a new signal
for C＝CH in the range of δ 6.32—6.58 in the 1H NMR
and two new signals for C＝CH and C＝CH appearing
in the range of δ 140.7—148.6 and δ 144.7—154.3 in
the 13C NMR spectra of the compounds 5a—5m. These
above facts clearly confirmed the synthesis of all final
products. All above compounds 1, 2, 3a—3m, 4a—4m
and 5a—5m were also synthesized by microwave
method. Yield and reaction time data were given in Ta-
ble 1.
Conclusion
Compound 5a—5m were synthesized by an effi-
cient route and screened for their antibacterial, antifun-
gal and antitubercular activity against selected micro-
1008
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© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 1001— 1010

Synthesis and Biological Study of Some 4-oxo-Thiazolidine Derivatives of 2-Aminothiazole
Table 1 Data of yield and reaction time of all synthesized compounds
Yield/%
Reaction time
Conv./h
Yield/%
Reaction time
Conv./h
Comp.
Comp.
Conv.
MW
MW/min
Conv.
MW
MW/min
1st stirring 2nd refluxing
1st stirring 2nd refluxing
1
62
70
60
64
67
65
66
65
63
64
62
61
60
61
62
64
65
65
66
60
64
77
86
78
86
84
85
84
83
80
77
78
80
81
79
80
76
79
85
82
81
83
6.15
5.00
3.00
3.15
3.15
3.15
2.30
3.30
3.30
3.30
3.30
3.30
3.30
3.30
3.30
2.45
2.30
2.45
2.30
2.30
2.15
—
—
4.00
3.10
3.35
3.40
3.35
4.10
3.15
3.10
2.40
3.15
3.30
2.55
3.50
4.15
3.25
3.30
3.35
3.15
3.10
3.30
3.00
4g
4h
4i
66
64
63
61
64
63
63
66
63
62
64
63
65
64
62
63
60
66
60
60
—
80
77
80
84
83
76
80
79
78
82
82
83
82
78
78
81
80
81
75
75
—
2.30
2.45
2.15
2.30
2.15
2.15
2.00
2.30
2.00
2.00
2.15
2.15
2.15
2.30
2.00
2.00
2.15
2.00
2.15
2.15
—
3.30
3.15
3.30
3.30
3.30
3.30
3.45
3.15
3.00
2.45
2.45
3.15
3.00
3.15
3.30
3.30
3.15
3.30
3.15
3.15
—
3.30
3.35
3.15
3.10
3.20
3.25
3.20
3.35
3.20
3.20
3.15
3.30
3.10
3.45
3.30
3.15
3.10
3.20
3.45
3.45
—
2
3a
3b
3c
3d
3e
3f
2.15
2.00
2.00
1.45
2.15
2.30
2.00
2.30
1.45
2.30
2.30
2.15
2.00
3.00
3.15
2.30
2.30
3.00
3.15
4j
4k
4l
4m
5a
5b
5c
5d
5e
5f
3g
3h
3i
3j
3k
3l
5g
5h
5i
3m
4a
4b
4c
4d
4e
4f
5j
5k
5l
5m
—
Table 2 Antibacterial and antifungal activities of compounds 5a—5ma
Antibacterial activity
Antifungal activity
A. flavus
50
Comp.
B. subtilis
E. coli
S. aureus
100
23
C. albicans
50
50
10
15
23
25
22
21
20
22
20
24
18
14
22
28
—
100
25
32
34
33
30
30
28
35
35
36
30
25
30
37
—
50
17
20
22
20
22
21
20
19
20
21
19
14
13
26
—
100
22
30
30
31
29
29
26
25
33
34
28
23
29
34
—
50
20
15
19
18
19
18
19
22
22
20
18
16
22
27
—
100
22
30
32
31
31
31
28
33
32
34
30
23
28
—
35
100
24
30
32
31
31
32
30
34
33
35
28
26
30
5a
5b
5c
5d
5e
5f
17
20
22
20
22
20
20
20
18
17
15
10
16
—
20
18
16
18
15
18
19
20
12
22
20
21
18
16
—
24
32
30
32
31
32
5g
5h
5i
27
33
32
5j
35
5k
5l
26
25
5m
28
Streptomycin
35
Griseofulvin
a Concentrations given in µg/mL.
—
36
Chin. J. Chem. 2011, 29, 1001— 1010
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1009

Samadhiya et al.
FULL PAPER
Table 3 Antitubercular activities of compounds 5a—5ma
Activity/%
Activity/%
Comp.
Activity/%
Comp.
Comp.
25
50
55
25
50
25
50
5a
5b
32
62
5f
5g
60
79
5k
5l
38
42
45
—
—
60
55
66
—
—
82
49
76
5c
63
80
5h
62
82
5m
—
—
5d
52
80
5i
57
83
5e
50
78
5j
58
81
Standard
100
100
Standard
100
100
Standard
100
100
a Concentrations given in µg/mL.
5
Gras, M.; Therrien, B.; S•s-Fink, G.; Casini, A.; Edafe, F.;
Dyson, P. J. J. Organomet. Chem. 2010, 695, 1119.
Siddiqui, N.; Ahsan, W. Eur. J. Med. Chem. 2010, 45, 1536.
Pandeya, S. N.; Sriram, D.; Nath, G.; DeClercq, E. Eur. J.
Pharm. Sci. 1999, 9, 25.
organisms. The investigation of antimicrobial data re-
vealed that the compounds 5c, 5d, 5e, 5f, 5h, 5i and 5j
displayed high activies in the series, compounds 5b, 5g
and 5m showed moderate activity and the rest com-
pounds showed less activity against all the strains com-
pared with standard drugs.
6
7
8
9
Sonwane, S. K.; Srivastava, S. D. Proc. Nat. Acad. Sci.
India 2008, 78, 129.
Acknowledgement
Lv, P.-C.; Wang, K.-R.; Yang, Y.; Mao, W.-J.; Chen, J.;
Xiong, J.; Zhu, H.-L. Bioorg. Med. Chem. Lett. 2009, 19,
6750.
The authors are thankful to SAIF, Central Drugs
Research Institute Lucknow (India) for providing spec-
tral and analytical data of the compounds. We are
thankful to Head, Department of Biotechnology, Dr. H.
S. Gour, University (A Central University), Sagar (India)
for antimicrobial (antibacterial and antifungal) and Mi-
crocare laboratory and Tuberculosis Research Center
Surat, Gujrat (India) for antituberculosis activity. We
are also thankful to Head, Department of Chemistry Dr.
H. S. Gour, University (A Central University), Sagar
(India) for giving the facilities to carry out the work.
10 Kazuaki, T.; Takeo, F.; Shiho, H.; Shigeyuki, C.; Kazuya, K.
Life Sci. 2002, 71, 947.
11 Scribner, A.; Meitz, S.; Fisher, M.; Wyvratt, M.; Leavitt, P.;
Liberator, P.; Gurnett, A.; Brown, C.; Mathew, J.; Thompson,
D.; Schmatz, D.; Biftu, T. Bioorg. Med. Chem. Lett. 2008,
18, 5263.
12 Xu, X. Y.; Qian, X. H.; Li, Z.; Song, G. H.; Chen, W. D. J.
Fluorine Chem. 2004, 125, 1159.
13 Asati, K.; Srivastava, S. K.; Srivastava, S. D. Chem. Indian
J. 2005, 1(10), 667.
14 Vazzana, I.; Terranova, E.; Mattioli, F.; Sparatore, F. Arkivoc
2004, 5, 364.
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