4
Tetrahedron Letters
Among all the derivatives screened, compound 9n, 9o and 9q
Table 3: in vitro antimicrobial activity of some of the
representative compounds of indazole-4-thiazolidinone
derivatives.
showed promising antimicrobial activity as well as anti-biofilm
activity. Based on their biological activities, these molecules
could be explored for further structural modifications in order to
develop promising lead molecules for various antimicrobial
therapies.
S. aureus
MLS16
MTCC
2940
K.
planticola
MTCC
530
B. subtilis
MTCC
121
M. luteus
MTCC
2470
Compound
9e
˃125
31.25
˃125
31.25
31.25
31.25
˃125
˃125
˃125
0.9
˃125
˃125
˃125
15.6
˃125
˃125
˃125
3.9
31.25
15.6
Aknowledgement
9g
9j
15.6
9n
3.9
SA and PVSR are thankful to Department of Pharmaceuticals,
Ministry of Chemicals and Fertilizers, Govt. of India, New Delhi
for the award of NIPER fellowship
9o
31.25
˃125
31.25
15.6
15.6
˃125
˃125
15.6
˃125
0.9
3.9
9q
3.9
9r
˃125
˃125
˃125
0.9
9s
9v
References and notes
31.25
0.9
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D. J. Med. Chem. 2005, 48, 2584-2588.
Ciprofloxacin
3.2. Minimum Bactericidal Concentration (MBC)
Further, compounds 9e, 9g, 9j, 9n, 9o, 9q, 9r, 9s and 9v were
examined to determine the minimum bactericidal concentration
(MBC) against B. subtilis MTCC 121, S. aureus MLS-16 MTCC
2940, M. luteus MTCC 2470 and K. planticola MTCC 530.
These results revealed that 9g, 9n, 9o and 9q displayed promising
bactericidal activity against K. planticola MTCC 530 (Table 4).
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A.; Chantry, D.; Eberhardt, C.; Oding, J.; Burgess, L. E. Bioorg.
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Table 4: MBC values of of some of the representative
compounds of indazole-4-thiazolidinone derivatives.
S.ab
K. pd
MTCC
530
4. Ottana, R.; Carotti, S.; Maccari, R.; Landini, I.; Chiricosta, G.;
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B. sa
M. lc
Compound
MLS16
MTCC 121
MTCC 2470
MTCC 2940
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9e
9g
9j
125
-
-
31.25
-
31.25
15.6
62.5
15.6
15.6
15.6
31.25
-
125
-
-
-
9n
9o
9q
9r
9s
9v
62.5
31.25
62.5
-
15.6
125
31.25
-
6. (a) Vigorita, M. G.; Previtera, T.; Basile, M.; Fenech, G.; Costa de
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31.25
125
-
-
-
-
62.5
31.25
62.5
-
-
aB. subtilis, bS. aureus, cM. luteus, dK. planticola
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3.3. Biofilm inhibition activity
Furthermore, we investigated whether these compounds exhibit a
specific anti-biofilm activity, or this observation was simply
related to a general toxic effect on the Gram-positive bacterial
strains.18 Compounds 9n, 9o and 9q were screened for specific
anti-biofilm activity against K. planticola MTCC 530, which is
an important nosocomial pathogen causing urinary tract
infection. These compounds exhibited promising activity (IC50
values ranging between 20.28–20.79 µg/mL) towards this
9.
(a) Rawal, R. K.; Srivastava, T.; Haq, W.; Katti, S. B. J. Chem.
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pathogen and the results are summarized in Table 5
.
Table 5: Biofilm assay values of compounds 9n, 9o and 9q
against K. planticola (IC50 values (µM))
Organism
K.
9n
9o
9q
Ciprofloxacin
0.5 0.10
20.28
0.11
20.72
0.02
20.79
0.02
planticola
MTCC 530
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4. Conclusions
In conclusion, we have developed a simple and convenient
protocol for the synthesis of 4-thiazolidinone derivatives via
multi-component strategy by employing VOSO4 as a catalyst and
ultrasonic irradiation was used as the energy source. The catalyst
could be recovered easily and reused for next four cycles thereby
reducing the waste. Furthermore, using this protocol a series of
novel indazole-4-thiazolidinones have been synthesized and
screened for their antimicrobial and anti-biofilm activities.
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