Baker's yeast catalyzed one-pot synthesis of bioactive 2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids

Article abstract of DOI:10.1515/hc-2017-0130

An efficient and simple one-pot protocol has been developed for synthesis of substituted derivatives of 2-hydrazono-4-thiazolidinone-5-acetic acids 4a-j and 6a-g by cyclocondensation of aryl/pyrazolyl aldehyde, thiosemicarbazide and maleic anhydride in acetonitrile in the presence of readily available whole cell biocatalyst, baker's yeast (Saccharomyces cerevisiae). The reaction is enhanced by ultrasonication.

Full text of DOI:10.1515/hc-2017-0130

Heterocycl. Commun. 2018; 24(2): 103–107
Anusaya S. Chavan, Arun S. Kharat, Manisha R. Bhosle and Ramrao A. Mane*
Baker’s yeast catalyzed one-pot synthesis of bioactive
2-[benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-
thiazolidin-4-one-5-yl-acetic acids
https://doi.org/10.1515/hc-2017-0130
Received June 25, 2017; accepted November 6, 2017; previously
published online March 21, 2018
from aldehydes [18, 19]. The aldehyde is condensed with
thiosemicarbazide and the resultant thiosemicarbazone
is then allowed to react with maleic anhydride by thia-
Michael addition to furnish the desired hydrazonothia-
zolidinone. Many hydrazonothiazolidinones have been
prepared by carrying one-pot tandem cyclocondensation
of aldehyde, maleic acid and thiosemicarbazide in toluene
in the presence of p-toluenesulfonic acid as catalyst under
microwave assisted irradiation at 100–120°C [18]. Hydra-
zonothiazolidinone acetic acids with a pyrazolyl scaffold
have been synthesized in a similar manner starting from a
pyrazolecarbaldehyde [17].
Abstract: An efficient and simple one-pot protocol has
been developed for synthesis of substituted derivatives
of 2-hydrazono-4-thiazolidinone-5-acetic acids 4a–j and
6a–g by cyclocondensation of aryl/pyrazolyl aldehyde,
thiosemicarbazide and maleic anhydride in acetonitrile
in the presence of readily available whole cell biocatalyst,
baker’s yeast (Saccharomyces cerevisiae). The reaction is
enhanced by ultrasonication.
Keywords: baker’s yeast; 2-hydrazono-4-thiazolidinon-
Enzymes are well explored as biocatalysts. Baker’s
5-yl-acetic acids; one-pot multicomponent reaction; yeast, one of the widely used whole cell source of biocata-
ultrasonication.
lysts [22–24] has been used to aid Hantzsch dihydropyri-
dine synthesis [25], synthesis of polyhydroquinoline [26],
Biginelli reaction for synthesis of dihydropyrimidinones
[27], aldol condensation and Knoevenagel condensation
[28]. It has been reported that biocatalysts display their
catalytic behavior even in organic solvents, making way
to easy solubilization of organic substrates [29–33].
Considering the information discussed above and in
continuation of our earlier work on biocatalysis [28, 34–
38], in this report we describe the use of activated baker’s
yeast as a source of a biocatalyst for accelerating the
synthesis of substituted 2-hydrazono-4-thiazolidinone-
5-acetic acids [17–21]. This report described an improved
approach to the synthesis of the desired products.
Introduction
Thiazolidinone ring system is a core component of peni-
cillins and cephalosporins and many derivatives display
a wide spectrum of therapeutic activities [1] including
antibacterial [2, 3], anti-inflammatory [4, 5], anticancer
[6–9], antitubercular [10], anticonvulsant [11], analgesic
[12], antimicrobial [12–15], and COX-2 inhibitory properties
[16]. 1,3-Thiazolidine-2,4-dione is an essential component
of clinical antidiabetic agents ciglitazone and pioglita-
zone and others bioactive compounds [17–20] (Figure 1).
In search for an efficient antidiabetic agent, chemists are
paying attention to synthesis of new 1,3-thiazolidin-4-ones
developing efficient synthetic protocols. Due to the thera- Results and discussion
peutic significance of hydrazono-4-thiazolidinone deriva-
tives, several protocols have been reported [17–21] for their A one-pot multi-component cyclocondensation pro-
synthesis. A two-step synthesis is usually used for obtain- tocol was developed for synthesis of aryl-substituted
ing 2-hydrazono-4-thiazolidinone-5-acetic acids starting 2-hydrazono-4-thiazolidine-1,3-one-5-acetic acids 4a–j
(Scheme 1) and pyrazol-4-yl substituted analogs 6a–g
(Scheme 2). The cornerstone of this work was finding
that baker’s yeast catalyzes these preparations. Ini-
tially, the cyclocondensation of benzaldehyde (1a), thio-
semicarbazide (2) and maleic anhydride (3) in ethanol
was run as a two-step model reaction. In the first step,
a mixture of benzaldehyde and thiosemicarbazide
was stirred in ethanol at room temperature in the pres-
ence of baker’s yeast for 4 h to furnish the intermediate
*Corresponding author: Ramrao A. Mane, Department of Chemistry,
Dr. Babasaheb Ambedkar Marathwada University, Aurangabad
431004, India, e-mail: manera2011@gmail.com
Anusaya S. Chavan and Manisha R. Bhosle: Department of
Chemistry, Dr. Babasaheb Ambedkar Marathwada University,
Aurangabad 431004, India
Arun S. Kharat: Department of Biotechnology, Dr. Babasaheb
Ambedkar Marathwada University, Aurangabad, Sub-Campus,
Osmanabad, India
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104ꢀ
ꢀA. S. Chavan et al.: 2-[Benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids
O
enzymes that catalyze the reaction. The use of ultrasoni-
S
cation at room temperature resulted in a remarkable
decrease of the reaction time from 48 h to 4 h. Interest-
ingly, an attempted reaction under ultrasonication but in
the absence of baker’s yeast did not produce any product
4a even after 40 h.
O
NH
S
NH
N
O
O
O
O
Pioglitazone
Ciglitazone
COOH
O
O
N
The model reaction was also screened using differ-
ent solvents and varying the temperature. It was found
that the reaction is best conducted in acetonitrile at
room temperature. The optimized conditions are given
in Experimental. Overall, products 4a–j (Scheme 1) were
obtained under the optimized conditions in the yields
varying from 82% to 93%. In a similar way, the pyrazole
analogs 6a–g (Scheme 2) were synthesized in the yields
of 71%–96%.
O
HOOC
S
O
Figure 1ꢀSelected bioactive agents with a thiazolidine-2,4-dione
scaffold.
S
NH2
CHO
N
S
H2N
O
N
H
N
Baker’s yeast
OH
HN
2
R
R
CH3CN, rt, )))))
O
O
1a–j
4a–j
O
3
O
a: R = H
b: R = 2-NO2
c: R = 4-F
d: R = 4-OMe
e: R = 4-OH
f: R = 4-Cl
g: R = 4-NMe2
h: PhCH = CHCHO (cinnamaldehyde)
i: R = 3,4-diOMe
j: R = 2-OH
Conclusion
An alternative environmentally friendly baker’s yeast-
catalyzed synthetic route to known 2-hydrazono-1,3-thi-
azolidin-4-ones-5-carboxylic acids 4a–j and 6a–g was
developed. Sonication-assisted disruption of the baker’s
yeast cell wall provides the intracellular enzymes that
catalyze the reaction. The synthesis is operationally
simple, is conducted at room temperature, and the
desired product is obtained in short reaction time and
with high yield.
Scheme 1ꢀSynthesis of compounds 4a–j.
thiosemicarbazone in 76% yield. Then the intermedi-
ate thiosemicarbazone was allowed to react with maleic
anhydride in ethanol in the presence of yeast at room
temperature. This treatment gave the desired product 4a
in 65% yield after 48 h. It was found that both steps are
catalyzed by baker’s yeast. This finding prompted us to
undertake cyclocondensation leading to 4a by the reac-
tion of benzaldehyde (1a), thiosemicarbazide (2) and
maleic anhydride (3) in ethanol in the presence of baker’s
yeast at room temperature as a one-step procedure. This
reaction furnished the desired product 4a after 48 h with
an enhanced yield of 70%.
Experimental
Melting points were determined in an open capillary tube and are
uncorrected. 13C NMR spectra were recorded in DMSO-d6 on a Bruker
AvIII HD-300 spectrometer operating at 75 MHz. The purity of prod-
ucts was checked by TLC using silica gel-coated aluminum sheets,
and visualization was accomplished by treatment with iodine or
exposure to ultraviolet light. The ultrasonication-assisted reactions
were carried out in a Bandelin Sonorexbath reactor operating at a
The use of ultrasonication for organic transforma-
tions is well explored [37]. The ultrasonication is also used
for disruption of the biological cells for the release of their
interiors [39–41]. In this work, ultrasonication was used to
disrupt baker’s yeast cells for the release of intracellular frequency of 35 kHz and a nominal power of 200 W.
S
a: R = H
NH2
N
N
N
N
H2N
O
N
H
b: R = Me
c: R = OMe
d: R = F
e: R = Br
f: R = NO2
Baker’s yeast
2
S
N
OH
O
N
CH3CN, rt, )))))
HN
R
R
O
O
5a–f
6a–f
O
3
O
Scheme 2ꢀSynthesis of compounds 6a–f.
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A. S. Chavan et al.: 2-[Benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acidsꢂ
ꢂ105
2-(3,4-Dimethoxybenzylidene)hydrazono)-1,3-thiazolidin-
4-one-5-acetic acid (4i) Yield 90%; off-white powder; mp 232–234°C;
13C NMR: δ 38.4, 44.5, 56.2, 114.4, 115.4, 122.5, 127.1, 149.5, 149.9, 152.1,
General procedure for synthesis of compounds 4a–j
A mixture of baker’s yeast (1 g) and acetonitrile (15 mL) was sonicated
at 35 kHz at room temperature for 30 min. After addition of a benzal-
dehyde 1a–j or a pyrazol-4-carbaldehyde 5a–f (5 mmol), thiosemicar-
bzide (5.5 mmol) and maleic anhydride (5.5 mmol) the mixture was
stirred at room temperature for an additional 3.5 h. The progress of
the reaction was monitored by thin layer chromatography on silica
gel using ethyl acetate/petroleum ether (2:8) as eluent. The mixture
was treated with ethyl acetate (30 mL), filtered through a pad of Celite
(1 g), and the filtrate was concentrated under reduced pressure. The
residue of product 4a–j was crystallized from ethanol. The mp’s and
spectral data for all compounds 4a–j are virtually identical with
those reported previously [1, 2].
+
177.0, 177.3. HRMS (ESI). Calcd for C14H15N3O5S (Mꢁ+ꢁH) : m/z 337.0732.
Found: m/z 337.0732.
2-(2-Hydroxybenzylidenehydrazono)-1,3-thiazolidin-4-one-
5-acetic acid (4j)ꢀYield 82%; off-white powder; mp 236–238°C; 13C
NMR: δ 38.4, 44.5, 115.0, 118.2, 121.8, 130.3, 135.2, 149.5, 158.6, 163,
+
177.0, 177.3. HRMS (ESI). Calcd for C12H11N3O4S (Mꢁ+ꢁH) : m/z 293.0470.
Found: m/z 293.0460.
General procedure for synthesis of compounds 6a–f
A mixture containing a pyrazole-4-carbaldehyde 5a–f and other rea-
gents as described above in acetonitrile (20 mL) was allowed to react
for 8 h. Workup was conducted as described above.
2-(N-Benzylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid
(4a)ꢀYield 93%; off-white powder; mp 252–254°C; 13C NMR: δ 36.7,
43.6, 127.7, 128.8, 130.7, 134.2, 156.3, 164.3, 171.7, 175.5. HRMS (ESI).
+
Calcd for C12H11N3O3S (Mꢁ+ꢁH) : m/z 278.0677. Found: m/z 278.0676.
2-[(1,3-Diphenylpyrazol-4-yl)methylenehydrazono]-1,3-thiazoli-
din-4-one-5-yl-acetic acid (6a)ꢀYield 82%; off-white powder; mp
263–265°C; 13C NMR: δ 36.8, 43.7, 116.7, 118.8, 127.1, 128.5 (2C), 128.6
(2C), 128.8 (2C), 129.5 (2C), 129.6, 132.0, 138.9, 149.1, 151.6, 171.7, 175.4;
2-(N-2-Nitrobenzylidene)2-hydrazono-1,3-thiazolidin-4-one-
5-acetic acid (4b)ꢀYield 92%; pale yellow powder; mp 270–271°C;
13C NMR: δ 36.8, 43.7, 120.5, 127.8, 128.9, 130.7, 156.3, 164.8, 171.6, 175.6.
+
MS (ESI): m/z 420 (Mꢁ+ꢁH) . Anal. Calcd for C21H17N5O3S: C, 60.13; H,
+
HRMS (ESI). Calcd for C12H10N4O5S (Mꢁ+ꢁH) : m/z 322.0411. Found: m/z
4.09; N, 16.70; S, 7.64. Found: C, 60.33; H, 4.04; N, 16.57; S, 7.61.
322.0410.
2-{[1-Phenyl-3-(4-methylphenyl)pyrazol-4-yl]methylene-
hydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6b)ꢀYield
96%; off-white powder; mp 230–232°C; 13C NMR: δ 20.9, 36.8, 43.7,
116.6, 118.8, 127.0, 128.5 (2C), 129.1 (2C), 129.6 (2C), 130.8, 138.0, 138.9,
2-(4-Flurobenzylidenehydrazono)-4-thiazolidinone-5-acetic
acid (4c)ꢀYield 90%; off-white powder; mp 276–278°C; 13C NMR:
δ 36.8, 43.6, 115.8, 116.1, 129.8, 129.9, 130.8, 130.9, 155.1, 165.2, 161.9,
+
171.8, 175.5. HRMS (ESI). Calcd for C12H10FN3O3S (Mꢁ+ꢁH) : m/z 296.0499.
+
149.2, 151.7, 162.7, 166.7, 171.8, 175.4; MS (ESI): m/z 434 (Mꢁ+ꢁH) . Anal.
Found: m/z 296.0499.
Calcd for C22H19N5O3S: C, 60.96; H, 4.42; N, 16.16; S, 7.40. Found: C,
61.00; H, 4.48; N, 16.20; S, 7.35.
2-(4-Methoxybenzylidenehydrazono)-1,3-thiazolidin-4-one-
5-acetic acid (4d)ꢀYield 93%; off-white powder; mp 254–256°C;
13C NMR: δ 36.7, 43.6, 55.2, 127.6, 128.9, 130.7, 134.3, 156.3, 164.3, 171.8
2-{[1-Phenyl-3-(4-methoxyphenyl)pyrazol-4-yl]methylene-
hydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6c)ꢀYield
80%; off-white powder; 242–243°C; 13C NMR: δ 36.9, 43.7, 55.2, 113.9,
114.3, 116.4, 118.8 (2C), 124.4 (2C), 126.9 (2C), 139.6, 130.0, 138.9, 149.3,
+
and 175.4. HRMS (ESI). Calcd for C13H13N3O4S (Mꢁ+ꢁH) : m/z 307.1356.
Found: m/z 307.1356.
+
151.5, 159.6, 162.7, 171.8, 175.5; MS (ESI): m/z 450 (Mꢁ+ꢁH) . Anal. Calcd
2-(4-Hydroxybenzylidenehydrazono)-1,3-thiazolidin-4-one-
5-carboxylic acid (4e)ꢀYield 85%; off-white powder; mp 255–257°C;
13C NMR: δ 36.7, 43.6, 126.3, 127.8, 134.3, 155.2, 164.4, 170.9 and 175.3.
for C22H19N5O4S: C, 58.79; H, 4.26; N, 15.58; S, 7.13. Found: C, 58.60; H,
4.30; N, 15.52 and S, 7.20.
+
HRMS (ESI). Calcd for C12H11N3O4S (Mꢁ+ꢁH) : m/z 293.1230. Found: m/z
2-{[1-Phenyl-3-(4-flurophenyl)pyrazol-4-yl]methylene-
hydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6d)ꢀYield
82%; off-white powder; mp 249–250°C; 13C NMR: δ 36.7, 43.7, 114.2,
115.2, 115.4, 117.2 (2C), 127.1 (2C), 128.6 (2C), 129.6, 130.8, 130.9, 138.8,
293.1220.
2-(4-Chlorobenzylidenehydrazono)-1,3-thiazolidin-4-one-5-ace-
tic acid (4f)ꢀYield 87%; off-white powder; mp 273–274°C; 13C NMR: δ
36.6, 43.5, 127.6, 128.8, 131.6, 133.2, 154.3, 164.3, 171.6 and 175.5. HRMS
+
150.4, 162.8, 163.5, 171.8 and 175.4; MS (ESI): m/z 438 (Mꢁ+ꢁH) . Anal.
Calcd for C21H16FN5O3S: C, 57.66; H, 3.69; 4.34; N, 16.01; S, 7.33. Found:
C, 57.60; H, 4.00; N, 16.08; S, 7.29.
+
(ESI). Calcd for C12H10ClN3O3S (Mꢁ+ꢁH) : m/z 311.0131. Found: m/z
311.0131.
2-{[1-Phenyl-3-(4-nitrophenyl)pyrazol-4-yl]methylene-
hydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6e)ꢀYield
78%; off-white powder; mp 260–262°C; 13C NMR: δ 36.7, 43.8, 117.5,
117.9, 118.7, 118.9 (2C), 123.9 (2C), 127.4 (2C), 128.9, 129.7, 131.4, 134.4,
2-(4-N,NDimethylaminobenzylidenehydrazono)-1,3-thiazolidin-
4-one-5-acetic acid (4g)ꢀYield 82%; off-white powder; mp 278–
279°C; 13C NMR: δ 36.9, 39.3, 43.6, 118.7, 119.4, 128.3, 130.7, 156.3, 164.4,
+
171.8, 175.5. HRMS (ESI). Calcd for C14H16N4O3S (Mꢁ+ꢁH) : m/z 320.0943.
+
138.8, 148.9, 163.2, 171.7 and 175.4; MS (ESI): m/z 465 (Mꢁ+ꢁH) . Anal.
Found: m/z 320.0944.
Calcd for C21H16N6O5S: C, 54.31; H, 3.47; N, 18.09; S, 6.90. Found: C,
54.60; H, 3.40; N, 18.04; S, 6.89.
2-(Cinnamylidenehydrazono)-1,3-thiazolidin-4-one-5-acetic acid
(4h)ꢀYield 84%; white powder; mp 192–194°C; 13C NMR: δ 36.7, 43.5, 2-{[1-Phenyl-3-(4-bromophenyl)pyrazol-4-yl]methylene-
119.4, 127.6, 128.7, 130.7, 134.3, 138.3, 156.3, 164.3, 171.6, 175.5. HRMS (ESI). hydrazono}-1,3-thiazolidin-4-one-5-yl-acetic acid (6f)ꢀYield
+
Calcd for C14H13N3O3S (Mꢁ+ꢁH) : m/z 304.0791. Found: m/z 304.0790.
71%; off-white powder; mp 200–202°C; 13C NMR: δ 38.4, 44.8, 106.1,
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106ꢀ ꢀA. S. Chavan et al.: 2-[Benzylidene(or pyrazol-4-ylmethylene)hydrazono]-1,3-thiazolidin-4-one-5-yl-acetic acids
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+
(Mꢁ+ꢁH) . Anal. Calcd for C21H16BrN5O3S: C, 50.61; H, 3.24; N, 14.05; S,
6.43. Found: C, 50.63; H, 3.19; N, 14.04; S, 6.39.
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