Synthesis, characterization and biological activity of 5-arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-phenyl-3,5-dihydro-4H-imidazol-4-ones

Article abstract of DOI:10.1155/2010/264036

Some novel 5-arylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-ones (6a-q) have been synthesized and characterized by elemental analyses, IR, NMR, and mass spectra. The products have been evaluated for antibacterial and a

Full text of DOI:10.1155/2010/264036

ISSN: 0973-4945; CODEN ECJHAO
E-Journal of Chemistry
2010, 7(1), 81-84
http://www.e-journals.net
Synthesis, Characterization and Biological Activity of
5-Arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-
phenyl-3,5-dihydro-4H-imidazol-4-ones
B. B. BALDANIYA
Chemistry Department, M G Science Institute,
Navarangpura, Ahmedabad-380 009, Gujarat, India.
bbbaldaniya@rediffmail.com
Received 12 May 2009; Accepted 5 July 2009
Abstract: Some novel 5-arylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-
phenyl-3,5-dihydro-4H-imidazol-4-ones (6a-q) have been synthesized and
characterized by elemental analyses, IR, NMR, and mass spectra. The products
have been evaluated for antibacterial and antifungal activities against different
strains of bacteria and fungi.
Keywords: Imidazole-4-one, Antibacterial activity, Antifungal activity.
Introduction
The imidazolinones1-6 have been associated with a wide range of therapeutic activities7-8
such as anticonvulsant, sedative and hypnotic, potent CNS depressant, antihistamine,
anti
filarial,
bactericidal,
fungicidal,
anti-inflammatory,
antiparkinsonian,
antihypertensive and anthelmintic. Recently new imidazoline derivatives were reported
for their anti-inflammatory, herbicidal and hypertensive activities9-10. The medicinal
utilities of compounds described in this section inspired us to synthesize some new
imidazolones. It is our ongoing project to synthesize new bioactive molecules11-12, we
have modified the 3rd position of imidazoline derivatives for potential and bioactive
heterocyclic compounds.
Erlenmeyer et al13 believed this synthesis to be a special type of Perkin condensation in
which reaction between aldehydes and acyl glycine proceeds first followed by ring closer. In
view of these observations we have synthesized imidazol-4-ones, 6a-q (Scheme 1, Table 1)
by the condensation of 6,7-dichloro-1,3-benzothiazol-2-amine (5) afforded the title
compounds with various oxazolinones 4a-q respectively (Scheme 1), the series of
compounds were characterization by IR, NMR, MS and elemental analysis.

82
B.B.BALDANIYA
O
Ar
O
O
Ar
O
(CH3CO)2O
+
+
H
N
H3C
O
N
O
H
OH
Na
O
3
1
2
4a-q
Cl
O
O
Ar
Cl
O
Ar
Cl
Cl
S
N
S
N
C5H5N
Reflux
N
+
H2N
N
N
6a-q
4a-q
5
Scheme 1
Table 1. Physical constant of the compounds (6a-q).
m.p. Yield,
%
C % N %
Calc. Found Calc.Found
Compd.
-Ar
Mol. Formula
ºC
-C6H5
C23H13Cl2N3OS
215
80 61.31 61.35 9.33 9.20
72 59.24 59.20 9.01 9.00
75 59.24 59.20 9.01 9.00
70 59.24 59.20 9.01 9.00
75 60.01 60.00 8.75 8.60
76 60.01 60.00 8.75 8.60
78 64.21 64.20 7.78 7.70
78 56.98 56.90 8.67 8.60
78 56.98 56.90 8.67 8.60
70 56.98 56.90 8.67 8.60
78 55.77 55.70 11.31 11.20
75 55.77 55.70 11.31 11.20
65 58.07 58.00 8.47 8.40
68 57.78 57.70 7.78 7.71
66 57.78 57.70 7.78 7.71
6a
6b
6c
6d
6e
6f
-2-OH-C6H4
-3-OH-C6H5
-4-OH-C6H2
-3-OCH3-C6H4
-4-OCH3-C6H4
-3-OC6H5-C6H4
-2-Cl-C6H4
C23H13Cl2N3O2S 175
C23H13Cl2N3O2S 235
C24H14BrCl2N3OS 240
C24H15Cl2N3O2S 260
C24H15Cl2N3O2S 245
C29H17Cl2N3O2S 240
6g
6h
6i
C23H12Cl3N3OS
C23H12Cl3N3OS
C23H12Cl3N3OS
C23H12Cl2N4O3S 215
C23H12Cl2N4O3S 210
245
210
220
-3-Cl-C6H4
-4-Cl-C6H4
-2-NO2-C6H4
-3-NO2-C6H4
6j
6k
6l
-3-OCH3-4-OH-C6H3 C24H15Cl2N3O3S 235
-2,4,5-(OCH3)3-C6H2 C26H19Cl2N3O4S 195
-3,4,5-(OCH3)3-C6H2 C26H19Cl2N3O4S 180
-5-Br-3-OCH3-4-OH-
C6H4
-2-OH-4-N(C2H5)2-
C6H3
6m
6n
6o
C23H13Cl2N3OS
250
65 50.11 50.00 7.30 7.20
70 60.34 60.30 10.42 10.40
6p
6q
C27H22Cl2N4O2S 230
Experimental
Melting points were taken in open capillaries using paraffin bath and are uncorrected. IR
1
spectra were recorded on FTIR-Perkin-Elmer spectrometer (υmax in cm-1); H NMR spectra
were recorded on BRUKER AVANCE 300 FT-NMR spectrometer using CDCl3 as a solvent
and Mass spectra carried out on JEOL SX 102/DA-600 mass spectrometer respectively. All
the compounds were analyzed for carbon, hydrogen and nitrogen and the result were
within 0.4% of theoretical values.

Synthesis, Characterizations and Biological Activity
83
5-Benzylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-
imidazol-4-one (6a)
A mixture of 6, 7-dichloro-1, 3-benzothiazol-2-amine15 (5) (0.01 mole) and 4-benzylidene-2-phenyl-
1, 3-oxazol-5(4H)-one (4a) (0.01 mole) was placed in a round bottom flask, 10 mL of pyridine was
added and mixture was refluxed on a sand bath for 5-6 h. The mixture was poured onto ice-cold
water and then required amount of con. HCl was added to neutralize it. The solid obtained was left
overnight, filtered, dried and than recrystallised from ethanol (99%). m.p.215 0C, Yield 80%, anal.
-1
found: C, 61.35; N, 9.20; calc for C23H13Cl2N3OS: C, 61.31; N, 9.33%. IR (KBr): 3001 cm (-C-H
str., aromatic), 1652 cm-1 (>C=O str., cyclic ring),1335 cm-1 (>C=N str., imidazol ring), 1309 cm-1
-1
-1
(-C-S-C, str., thiazol ring), 1278 cm (-C-N, tertiary amine), 963 cm (-C-Cl str., aromatic),746 cm-1
(>C=CH, medium), 688,613 cm-1 (disubstituted aromatic). 1H NMR(CDCl3): δ ppm 7.2 δ (s, 1H ,
-CH), 7.26-8.54 δ (m, 11H, Ar-H,-C=CHAr). MS: m/z 451.01 with 69% relative intensity
[M+]. The compounds (6b-q) similarly prepared, their m.p.s and yields are given in Table 1.
Biological activity
Antibacterial activity
Antibacterial activity was carried out by broth dilution method14 (Table 2). The strains used
for the activity were procured from Institute of Microbial Technology, Chandigarh.
Table 2. Antibacterial activity of synthesized compounds.
Antifungal activity is expressed in
Antimicrobial activity is expressed in the form of
the form of Minimal Fungicidal
Minimum Bactericidal Concentration (MBC)
Concentration
Compd E. coli P. aeruginosa S. aureus S. pyogenus C. albicans A. niger A. clavatus
MTCC
443
200
100
250
50
MTCC
1688
250
500
250
100
500
250
250
250
200
100
200
250
250
500
500
200
250
MTCC
96
MTCC
442
1000
1000
200
500
1000
500
500
100
200
250
250
250
500
500
500
500
500
MTCC
227
1000
500
200
200
1000
500
500
1000
500
500
500
500
500
500
500
500
500
MTCC
282
1000
500
200
200
1000
500
500
1000
500
500
500
500
500
500
500
500
500
MTCC
1323
1000
500
1000
500
100
500
500
500
500
50
6a
6b
6c
6d
6e
6f
6g
6h
6i
200
200
500
200
200
100
100
50
1000
500
500
1000
500
500
200
100
50
6j
100
200
200
500
500
200
100
500
500
6k
6l
50
500
50
500
500
6m
6n
6o
6p
6q
500
500
500
500
500
500
For antibacterial activity, in present protocol 100 µg/mL is considered as moderately active, 50 µg/mL
is considered as good activity and 25 µg/mL is considered as active as compared to the standard drug
gentamycin. For antifungal activity, 200 µg/mL is considered as moderately active, 100 µg/mL is
considered as active as compared to standard drug Nystatin

84
B.B.BALDANIYA
Antifungal activity
Same compounds were tested for antifungal activity against C. albicans A. niger and A.
clavatus at a concentrations of 1000, 500, 200, and 100 µg/mL respectively (Table 2).
The standard drug used in the present study was “Gentamycin” for evaluating
antibacterial activity which showed (0.25, 0.05, 0.5 & 1 µg/mL MBC against S. aureus, E.
pyogenes and P. aeruginosa respectively. “K. Nystatin” was used as the standard drug for
antifungal activity which showed 100 µg/mL MFC against fungi, used for the antifungal
activity.
Acknowledgements
The authors are thankful to the authority of Bhavnagar University, Bhvnagar and St. Xaviers
Research Foundation, St. Xaviers College, Ahmedabad, for providing research facilities. We
are also thankful to Director, FSL Gandhinagar for recording the spectra and thankful to
UGC for financial support (F No. 47-027/07)
References
1
Upadhyay P S, Joshi H D, Baxi A J and Prikh A R, Indian J Heterocycl Chem.,
1991, 1, 71.
2
3
Harfenist M, Soroko E F and Mekenzie G M, J Med Chem., 1978, 21, 405.
Meenaxi Shrimali, Reena Kalsi, Renu Sah , Dixit K S, Nath C and Barthwal J P,
Indian J Chem., 1990, 29B, 85.
4
5
6
Rama Sarma G V S and Reddy V M, Indian J Heterocycl Chem., 1993, 3, 111.
Tripathi and Pradip K, Indian J Heterocycl Chem., 2004, 14(1), 77-78.
Hirpara K V, Patel S P, Parikh K A, Bhimani A S and Parikh H H, J Science, Islamic
Republic of Iran., 2004, 15(2), 135.
7
Mukherji D, Nautiyi S R and Prasad C R, Indian Drugs, 1981, 18, 125.
Upadhyay P S, Joshi S N, Baxi A J and Parikh A R, J Indian Chem Soc., 1991, 68, 364.
Saxena S, Verma M, Saxena A K and Shanker K, Indian J Heterocycl Chem., 1991, 1, 34.
Misra Upma, Pathak A K and Tiwari D C, Indian Drugs, 1990, 27, 697.
Desai N C, Shah M D, Keshav K A and Saxena A K, Indian J Chem., 2001, 40B, 201.
Desai N C, Bhatt J J, Patel H H, Undavia N K and Trivedi P B, Indian J Chem., 1995,
34B, 201.
8
9
10
11
12
13
14
Erlenmeyer E and Stadlin W, Liebigs Ann., 1904, 337, 283.
National Committee for Clinical Laboratory Standard. Reference method for broth
dilution antifungal susceptibility testing of yeasts Approved standard M27A. 1997,
NCCLS, Wayne, PA.
15
Organic synthesis; Collective vol.3; Noland, Wayland E., Editor in-Chief;John Wiley
& Sons Inc. New York, 1962, 76.
.

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