Synthesis, characterization, and biological activity of some new benzoic acid and thiazoloacridine derivatives

Article abstract of DOI:10.1080/10426500701852687

A series of acridine derivatives 5have been synthesized by cylization of benzoic acid derivatives 4using POCl3. Compounds 4 were synthesized by Ullamnn Condensation of bromo derivatives 2 and substituted anthranilic acid, respectively, which in turn have

Full text of DOI:10.1080/10426500701852687

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Phosphorus, Sulfur, and Silicon
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Synthesis, Characterization,
and Biological Activity of
Some New Benzoic Acid and
Thiazoloacridine Derivatives
Nilav A. Patel a , Sandip C. Surti a , R. G. Patel a &
M. P. Patel a
a Department of Chemistry , Sardar Patel
University , Vallabh Vidyanagar, Gujarat, India
Published online: 12 Aug 2008.
To cite this article: Nilav A. Patel , Sandip C. Surti , R. G. Patel & M. P. Patel (2008)
Synthesis, Characterization, and Biological Activity of Some New Benzoic Acid
and Thiazoloacridine Derivatives, Phosphorus, Sulfur, and Silicon and the Related
Elements, 183:9, 2191-2203, DOI: 10.1080/10426500701852687
To link to this article: http://dx.doi.org/10.1080/10426500701852687
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Phosphorus, Sulfur, and Silicon, 183:2191–2203, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701852687
Synthesis, Characterization, and Biological Activity of
Some New Benzoic Acid and Thiazoloacridine Derivatives
Nilav A. Patel, Sandip C. Surti, R. G. Patel, and M. P. Patel
Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar,
Gujarat, India
A series of acridine derivatives 5 have been synthesized by cylization of benzoic acid
derivatives 4 using POCl3. Compounds 4 were synthesized by Ullamnn Conden-
sation of bromo derivatives 2 and substituted anthranilic acid, respectively, which
in turn have been prepared from the Schiff bases of 4-aryl-2-amino thiazole 1 and
substituted aldehydes. Biological activities of all the compounds have been studied
using gram positive and gram negative bacteria and their anti-fungal activity us-
ing fungal species Aspergillus Parasiticus and Sclerotium Rolfsii. All structures of
the newly synthesized heterocyclic compounds were established based on elemental
analyses, IR, 1H NMR, 13C NMR, and mass spectra.
Keywords Arylaminothiazole; biological activity; thiazoloacridine; thiazoloamino ben-
zoic acid
INTRODUCTION
Thiazoles are familiar group of heterocyclic compounds possessing a
wide variety of biological activities and their utility as medicaments
is very much established.1–4 Thiazole nucleus is also integral part
of all the available penicillin’s, which have revolutionized the ther-
apy of bacterial diseases.5–10 A detailed literature survey11,12 reveal
that a large number of thiazole derivatives containing other hetero-
cyclic system have been designed synthesized and evaluated for their
antimicrobial activity involving several strains of bacteria, fungi and
viruses.13–16 Schiff bases play an important role in many biological pro-
17–21
cesses. Their ready synthesis and numerous biological activities
contributed greatly to their popularity. Acridine and its derivatives,
Received 29 September 2007; accepted 28 November 2007.
The authors are thankful to Dr. K C Patel and Mr. Kishor H Chauhan, Department of
Biosciences, Sardar Patel University, for providing facilities for the antibacterial activity
and SAIF, Punjab University, for 1H NMR and 13C NMR Spectra.
Address correspondence to M. P. Patel, Department of Chemistry, Sardar Patel Univer-
sity, Vallabh Vidyanagar-388 120, Gujarat, India. E-mail: patelmanish1069@yahoo.com
2191

2192
N. A. Patel et al.
well known as DNA intercalates, have been widely studied from a va-
riety of viewpoints, such as synthesis,22 physicochemical properties,23
structural requirement,24 biological activities,25 anticancer activity,26
antimalarial,27 and anti-inflammatory28 activities. The above short-
comings have motivated our research, and we considered it worthwhile
to synthesize variety of thiazoloacridine derivatives and to study their
biological activity.
RESULTS AND DISCUSSION
4-aryl-2-aminothiazole 1 was prepared by the solid phase reaction of
thiourea, 4-bromo acetophenone and iodine. The 4-aryl-2-aminothiazole
1 was reacted with substituted aldehydes to obtain Schiff base deriva-
tives containing thiazole moiety 2. The compounds 2 were reacted with
substituted anthranilic acids 3 to give benzoic acid derivatives 4. These
benzoic acid derivatives 4 were cyclized in the presence of POCl3 to ob-
tain acridine derivatives 5 (Scheme 1). All synthesized compounds were
well characterized by their elemental analysis, IR, 1H NMR, 13C NMR
spectral studies and continues monitoring of TLC during the reaction.
The IR spectra of compounds 4a–l showed absorption band in the
region of 1700–1730 cm−1 (>C O str.). The 1H NMR (DMSO-d6) spectra
of compounds 4a-l exhibited the signal around 8.0–9.0 δ value of ( NH),
11.5–12.0 δ of ( COOH) and the 13C NMR spectra of compounds 4a-
l exhibited the peak around δ 160–170 value confirms the assumed
structure of benzoic acid derivatives. The IR spectra of compounds 5a–l
showed the disappearance of (>C O str. and NH str.) band. 1H NMR
(DMSO-d6) of 5a–l exhibited the disappearance of the sharp singlet
(around 8.0–9.0 δ value of ( NH) and 11.5–12.0 δ value of ( COOH))
and in 13C NMR disappearance of the signal around δ 160–170 confirms
the cyclization of benzoic acid derivatives to acridine derivatives.
BIOLOGICAL ACTIVITY
Antibacterial Activity
Anti-bacterial activities of synthesized compounds were examined
in vitro by known agar diffusion cup method.29–32 All the compounds
were tested for activity against gram-positive bacteria like Bacillus
cereus, and Bacillus subtilis and gram-negative bacteria Escherichia
coli. The culture medium was nutrient agar. All compounds were dis-
solved in N,N’-dimethylformamide (DMF). DMF was used as control.
Antibacterial activity was determined by measuring the diameter of
the inhibition zone. All the compounds were screened with reference

Benzoic Acid and Thiazoloacridine Derivatives
2193
Compd.
R
R1
Compd.
R
R1
4a
4b
4c
4d
4e
4f
4-H
H
H
H
H
Br
Br
5a
5b
5c
5d
5e
5f
4-H
H
H
H
H
Br
Br
4-OH
4-OCH3
3-NO2
4-H
4-OH
4-OCH3
3-NO2
4-H
4-OH
4-OH
4g
4h
4i
4-OCH3 Br
5g
5h
4-OCH3 Br
3-NO2
4-H
Br
NO2 5i
NO2 5j
3-NO2
4-H
Br
NO2
NO2
4j
4-OH
4-OH
4k
4l
4-OCH3 NO2 5k
3-NO2 NO2 5l
4-OCH3 NO2
3-NO2 NO2
SCHEME 1

2194
N. A. Patel et al.
TABLE I Antibacterial Screening Results of the Compounds 4a-l and
5a-l
Inhibition zone (mm)
Inhibition zone (mm)
Compd.
B.subtilis B.cereus E.coli
Compd.
B.subtilis B.cereus E.coli
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
7
10
7
8
7
7
7
6
6
8
7
7
17
35
7
10
6
9
8
9
8
6
7
14
6
6
14
29
14
14
14
12
12
11
12
12
11
11
12
13
15
40
5a
5b
5c
5d
5e
5f
5g
5h
9
7
7
6
5
6
7
6
6
7
8
7
17
35
10
6
7
8
6
7
7
7
6
6
7
8
14
29
14
11
10
12
11
10
10
10
13
12
12
13
15
40
5i
5j
5k
5l
Ampicillin
Ciprofloxacin
Ampicillin
Ciprofloxacin
to standard drugs Ciprofloxacin and Ampicillin. The results are sum-
marized in Table I. It is observed that the compounds having hydroxyl
group in 4b and 4j show good activity against gram positive bacteria
B.Subtilus and B.Cereus, as well as gram negative bacteria Escherichia
coli compared to standard drug Ampicillin, while moderately active
against Ciprofloxacin. Compounds 5a, 5d, 5i, and 5j are moderately ac-
tive against gram-negative bacteria Escherichia coli compared to stan-
dard drug Ampicillin.
Antifungal Activity
The control DMF, commercial fungicides, and newly synthesized
compounds have been tested for their effect on the growth of fungal
cultures (Aspergillus parasiticus and Sclerotium rolfsii) using plate
poison technique.33,34 The results are summarized in Table II. It is ob-
served that the compounds containing dibromo group in 4e, 4f, and 4g
show good activity and 5e, 5f, and 5g are moderately active against
Aspergillus parasiticus and Sclerotium rolfsii compared to std. drug
Griseofulvin.
EXPERIMENTAL
All melting points were taken in open capillaries and are uncorrected.
IR spectra were recorded in KBr on a Nicolet 400D spectrophotometer
and only characteristic peaks are reported. 1H NMR and 13C NMR were

Benzoic Acid and Thiazoloacridine Derivatives
2195
TABLE II Antifungal Screening Results of the Compounds 4a-l and
5a-l
Inhibition (%)
Inhibition (%)
Aspergillus
parasiticus
Sclerotium
rolfsii
Aspergillus
parasiticus
Sclerotium
rolfsii
Compd.
Compd.
4a
4b
4c
4d
4e
4f
4g
4h
4i
4j
4k
4l
69.94
78.20
80.62
82.76
80.91
85.47
85.61
76.78
80.91
79.34
82.47
77.92
100
65.45
74.60
77.60
78.86
80.91
82.49
81.86
76.18
78.07
77.60
79.33
75.70
100
5a
5b
5c
5d
5e
5f
5g
5h
5i
5j
5k
5l
68.51
71.08
69.51
66.95
71.08
72.36
73.64
71.36
68.09
66.95
69.94
68.09
100
63.72
66.56
64.51
63.56
67.82
71.45
69.24
66.71
63.88
64.66
66.40
66.08
100
Griseofulvin
Griseofulvin
recorded in DMSO-d6 on a Bruker AC 300F (300 MHz) using TMS as
an internal standard. Chemical shifts are reported in parts per million
(ppm). Thin layer chromatography (TLC) was performed on silica gel
G for TLC (Merck) and spots were visualized by iodine vapors or by
irradiation with ultraviolet light.
General Procedure
2-((4-[2-((1E)-1-aza-2-phenylvinyl) 1,3-thiazol-4-yl] phenyl)
amino) Benzoic Acid (4a)
A mixture of substituted anthranilic acid (1.37 g, 0.01 mol) in
dimethyl formamide (5 ml) and (3.43 g, 0.01 mo)l of compound 2 were
refluxed for 12–15 h in the presence of K2CO3(1.08 g, 0.01 mole) and 2%
cu-powder. The resulting clear solution was cooled, poured onto 100 g
of crushed ice, and HCl (25 ml) was added to it, while stirring. The
solid product, thus obtained was filtered and washed thoroughly with
water, dried, and crystallized from chloroform to give compound 4a. All
the other compounds (4b-l) have been synthesized following the same
method.
2-[(1E)-1-aza-2-(phenyl)vinyl]-4-(9-chloroacridin-2-yl)-1,
3-thiazole (5a)
Compound 4a (3.99 g, 0.01 mol) and POCl3 (30 ml) were taken in flask
and the reaction mixture was refluxed for 14–15 h. The excess solvent

2196
N. A. Patel et al.
was distilled out, and the resulting clear solution was cooled, poured
onto crushed ice, and the solid thus separated was filtered, washed thor-
oughly with water, dried, and crystallized from dimethyl formamide to
give compound 5a. All the other compounds (5b-l) have been synthe-
sized using the same method.
2-((4-[2-((1E)-1-aza-2-phenylvinyl) 1,3-thiazol-4-yl]phenyl)
amino) Benzoic Acid (4a)
M.p. 140–141◦C, Yield 59%, anal. calcd. for C23H17N3O2S: C 69.15,
1
H 4.28, N 10.51; found C 69.01, H 4.13, N 10.40. H NMR δH (DMSO-
d6, 300 MHz) 6.82–7.71 (14H, m, Ar-H), 6.01 (1H,s, N CH), 12.0 (1H, s,
COOH), 8.01 (1H,s, NH). IR: νmax (KBr, cm−1) 1720 (C O stret.) 2800
(O H stret. in COOH), 3330 (NH stret.) 1340 (C N stret.). 13C NMR δc
(DMSO-d6) 114.0, 124.4, 125.6, 126.4, 128.1, 129.0, 129.4, 129.6, 130.4,
131.8, 133.8, 134.2, 135.6, 137.4, 138.0, 138.8, 145.6, 146.8, 152.1, 152.7,
166.8.
2-((4-[2-((1E)-1-aza-2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-4-yl)
phenyl) amino) Benzoic Acid (4b)
M.p. 159–160◦C, Yield 55%, anal. calcd. for C23H17N3O3S: C 66.49, H
1
4.12, N 10.11; found C 66.31, H 4.03, N 10.25. H NMR δH (DMSO-d6,
300 MHz) 6.81–7.72 (13H,m, Ar-H), 6.03 (1H,s, N CH), 12.01 (1H,s,
COOH), 8.02 (1H,s, NH) 4.6 (1H, s, OH). IR: νmax (KBr, cm−1) 1725
(C O stret.) 2809 (O H stret. in COOH), 3331 (NH stret.) 1341 (C N
stret.) 3127 (O H stret.). 13C NMR δc (DMSO-d6) 114.1, 124.2, 125.5,
126.3, 128.0, 129.2, 129.6, 129.8, 130.5, 131.6, 133.7, 134.1, 135.5, 137.3,
138.2, 138.5, 145.6, 146.4, 152.2, 152.6, 166.6.
2-((4-[2-((1E)-1-aza-2-(4-methoxyphenyl) vinyl]-1,3-thiazol-4-yl)
phenyl) amino) Benzoic Acid (4c)
M.p. 147–148◦C, Yield 53%, anal. calcd. for C24H19N3O3S: C 67.11,
H 4.45, N 9.78; found C 67.01, H 4.33, N 9.90. 1H NMR δH (DMSO-d6,
300 MHz) 6.80–7.73 (13H,m, Ar-H), 6.04 (1H,s, N CH), 12.03 (1H,s,
COOH), 8.04 (1H,s, NH) 3.75 (3H, s, OCH3). IR: νmax (KBr, cm−1
)
1721 (C O stret.) 2804 (O H stret. in COOH), 3334 (NH stret.) 1345
(C N stret.). 13C NMR δc (DMSO-d6) 56.8, 114.2, 124.3, 125.5, 126.1,
128.3, 129.6, 129.8, 129.9, 130.5, 131.6, 133.6, 134.4, 135.8, 137.3, 138.2,
138.9, 145.5, 146.2, 152.3, 152.4, 166.6.
2-((4-[2-((1E)-1-aza-2-(3-nitrophenyl)vinyl]-1,3-thiazol-4-yl)
phenyl) amino) Benzoic Acid (4d)
M.p. 151–52◦C, Yield 47%, anal. calcd. for C23H16N4O4S: C 62.15, H
1
3.62, N 12.60; found C 62.01, H 3.53, N 12.46. H NMR δH (DMSO-d6,

Benzoic Acid and Thiazoloacridine Derivatives
2197
300 MHz) 6.72–7.75 (13H,m, Ar-H), 6.05 (1H,s, N CH), 11.90 (1H,s,
COOH), 7.91 (1H,s, NH). IR: νmax (KBr, cm−1) 1723 (C O stret.)
2809 (O H stret. in COOH), 3338 (NH stret.) 1354 and 1536 (NO2
stret.), 1346 (C N stret.). 13C NMRδc(DMSOd6)114.8, 124.1, 125.9,
126.8, 128.4, 128.6, 129.5, 129.8, 129.9, 130.2, 131.5, 132.4, 133.3, 134.4,
135.3, 137.2, 138.4, 138.3, 145.1, 146.4, 152.7, 152.5, 166.3.
2-((4-[2-((1E)-1-aza-2-phenylvinyl) 1,3-thiazol-4-yl]phenyl)
amino)-5-bromo Benzoic Acid (4e)
M.p. 145–146◦C, Yield 49%, anal. calcd. for C23H16BrN3O3S: C 57.74,
1
H 3.37, N 8.78; found C 57.61, H 3.23, N 8.65 H NMR δH (DMSO-d6,
300 MHz) 6.85–7.79 (13H,m, Ar H), 6.03 (1H,s, N CH), 12.06 (1H,s,
COOH), 8.05 (1H,s, NH). IR: νmax (KBr, cm−1) 1720 (C O stret.) 2800
(O H stret. in COOH), 559 (C Br stret.) 3330 (NH stret.) 1340 (C N
stret.). 13C NMR δc (DMSOd6)114.5, 124.6, 125.7, 126.2, 128.2, 129.6,
129.1, 129.4, 130.3, 131.4, 133.5, 134.1, 135.5, 137.5, 138.3, 138.7, 145.3,
146.2, 152.4, 152.3, 166.4.
2-((4-[2-((1E)-1-aza-2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-4-yl)
phenyl)amino)-5-bromo Benzoic Acid (4f)
M.p. 168–169◦C, Yield 56%, anal. calcd. for C23H16BrN3O3S: C 55.88,
H 3.26, N 8.50; found C 55.76, H 3.16, N 8.45. 1H NMR δH (DMSO-d6,
300 MHz) 6.82–7.71 (12H,m, Ar H), 6.05 (1H,s, N CH), 12.06 (1H,s,
COOH), 8.04 (1H,s, NH) 4.5 (1H, s, OH). IR: νmax (KBr, cm−1) 1729
(C O stret.) 2811 (O H stret. in COOH), 3336 (NH stret.) 552 (C Br
stret.) 1349 (C N stret.) 3126(OHstret.). 13C NMRδc(DMSOd6)114.2,
124.3, 125.6, 126.4, 128.1, 129.3, 129.5, 129.9, 130.6, 131.2, 133.6, 134.2,
135.4, 137.6, 138.5, 138.1, 145.5, 146.7, 152.4, 152.5, 166.7.
2-((4-[2-((1E)-1-aza-2-(4-methoxyphenyl)vinyl]-1,
3-thiazol-4-yl)phenyl)amino)-5-bromo Benzoic Acid (4g)
M.p. 157–158◦C, Yield 53%, anal. Calcd. for C24H18BrN3O3S: C 56.70,
H 3.56, N 8.26; found C 56.61, H 3.43, N 8.35. 1H NMR δH (DMSO-d6,
300 MHz) 6.88–7.79 (12H,m, Ar H), 6.02 (1H,s, N CH), 12.05 (1H,s,
COOH), 8.06 (1H,s, NH) 3.72 (3H, s, OCH3). IR: νmax (KBr, cm−1
)
1720 (C O stret.) 2806 (O H stret. In COOH), 3333 (NH stret.),
554 (C Br stret.), 1349 (C N stret.). 13C NMRδc(DMSOd6)56.4, 114.1,
124.5, 125.4, 126.0, 128.3, 129.4, 129.6, 130.2, 131.3, 133.4, 134.6, 135.4,
137.7, 138.6, 138.4, 145.6, 146.3, 152.4, 152.6, 166.5.

2198
N. A. Patel et al.
2-((4-[2-((1E)-1-aza-2-(3-nitrophenyl)vinyl]-1,3-thiazol-4-yl)
phenyl)amino)-5-bormo Benzoic Acid (4h)
M.p. 171–172◦C, Yield 45%, anal. calcd. for C23H15BrN4O4S: C 52.78,
H 2.88, N 10.70; found C 52.85, H 2.99, N 10.82. 1H NMR δH (DMSO-d6,
300 MHz) 6.71–7.78 (12H,m, Ar-H), 6.02 (1H,s, N CH), 11.80 (1H,s,
COOH), 7.90 (1H,s, NH). IR: νmax (KBr, cm−1) 1724 (C O stret.)
2806 (O H stret. in COOH), 3335 (NH stret.), 555 (C Br stret.),
1355 and 1532 (NO2 stret.), 1347 (C N stret.). 13C NMR δc (DMSO-d6)
114.2,124.0,125.6, 126.2, 128.2, 128.5, 129.3, 129.5, 129.7, 130.9, 131.8,
132.6, 133.5, 134.2, 135.4, 137.5, 138.3, 138.7, 145.5, 146.6, 152.2, 152.6,
166.4.
2-((4-[2-((1E)-1-aza-2-(phenyl)vinyl)1,3-thiazol-4-yl] phenyl)
amino)-5-nitrobenzoic Acid (4i)
M.p. 138–139◦C, Yield 47%, anal. calcd. for C23H16N4O4S: C 62.15,
1
H 3.62, N 12.60; found C 62.01, H 3.53, N 12.44. H NMR δH (DMSO-
d6, 300 MHz) 6.86–7.74 (12H,m, Ar-H), 6.07 (1H,s, N CH), 12.03 (1H,s,
COOH), 8.04 (1H,s, NH). IR: νmax (KBr, cm−1) 1721 (C O stret.) 2802
(O H stret. in COOH), 3339 (NH stret.), 1351 and 1532 (NO2 stret.),
1339 (C N stret.). 13C NMR δc (DMSO-d6) 114.9, 124.1, 125.5, 126.1,
128.6, 129.1, 129.5, 129.7, 130.3, 131.9, 133.7, 134.1, 135.5, 137.3, 138.2,
138.4, 145.3, 146.4, 152.5, 152.4, 166.1.
2-((4-[2-((1E)-1-aza-2-(4-hydroxyphenyl)vinyl]-1,3-thiazol-4-yl)
phenyl) amino)-5-nitrobenzoic Acid (4j)
M.p. 155–156◦C, Yield 51%, anal. calcd. for C23H16N4O5S: C 59.99,
H 3.50, N 12.16; found C 59.86, H 3.62, N 12.25. 1H NMR δH (DMSO-d6,
300 MHz) 6.88–7.77 (12H,m, Ar H), 6.07 (1H,s, N CH), 12.09 (1H,s,
COOH), 8.05 (1H,s, NH) 4.7 (1H, s, OH). IR: νmax (KBr, cm−1) 1729
(C O stret.) 2802 (O H stret. in COOH), 1352 and 1533 (NO2 stret.),
3339 (NH stret.) 1344 (C N stret.), 3126 (O H stret.). 13C NMR δc
(DMSO-d6) 114.5, 124.5, 125.4, 126.6, 128.1, 129.1, 129.5, 129.7, 130.4,
131.5, 133.6, 134.0, 135.6, 137.4, 138.1, 138.4, 145.5, 146.3, 152.1, 152.4,
166.1.
2-((4-[2-((1E)-1-aza-2-(4-methoxyphenyl)vinyl]-1,3-thiazol-4-yl)
phenyl) amino)-5-nitrobenzoic acid (4k)
M.p. 162–163◦C, Yield 55%, anal. calcd. for C24H18N4O5S: C 60.75,
H 3.82, N11.80; found C 60.86, H 3.73, N 11.91. 1H NMR δH (DMSO-d6,
300 MHz) 6.85–7.72 (12H,m, Ar H), 6.02 (1H,s, N CH), 12.01 (1H,s,
COOH), 8.03 (1H,s, NH) 3.79 (3H, s, OCH3). IR: νmax (KBr, cm−1
)
1722 (C O stret.) 2804 (O H stret. in COOH), 1357 and 1538 (NO2

Benzoic Acid and Thiazoloacridine Derivatives
2199
stret.), 3336 (NH stret.) 1349 (C N stret.). 13C NMR δc (DMSO-d6) 56.5,
114.1, 124.2, 125.6, 126.2, 128.7, 129.8, 129.9, 130.4, 130.6, 131.7, 133.4,
134.6, 135.9, 137.7, 138.5, 138.4, 145.6, 146.4, 152.6, 152.7, 166.3.
2-((4-[2-((1E)-1-aza-2-(3-nitrophenyl)vinyl]-1,3-thiazol-4-yl)
phenyl) amino)-5-nitrobenzoic Acid (4l)
M.p. 157–158◦C, Yield 47%, anal. calcd. for C23H15N5O6S: C 56.44,
H 3.08, N 14.30; found C 56.33, H 3.03, N 14.46. 1H NMR δH (DMSO-d6,
300 MHz) 6.70–7.71 (12H,m, Ar H), 6.07 (1H,s, N CH), 11.80 (1H,s,
COOH), 7.95 (1H,s, NH). IR: νmax (KBr, cm−1) 1730 (C O stret.) 2811
(O H stret. in COOH), 3340 (NH stret.) 1359 and 1540 (NO2 stret.),
1344 (C N stret.). 13C NMR δc (DMSO-d6) 114.2, 124.2, 125.1, 126.2,
128.5, 128.2, 129.1, 129.3, 129.4, 130.4, 131.1, 132.6, 133.1, 134.6, 135.4,
137.6, 138.3, 138.1, 145.2, 146.5, 152.8, 152.6, 166.4.
2-[(1E)-1-aza-2-(phenyl)vinyl]-4-(9-chloroacridin-2-yl)-1,
3-thiazole (5a)
M.p. 181–182◦C, Yield 43%, anal. calcd. for C23H14ClN3S: C 69.05, H
1
3.52, N 10.50; found C 69.16, H 3.63, N 10.40. H NMR δH (DMSO-d6,
300 MHz) 6.82–7.65 (12H,m, Ar H), 6.0 (1H,s, N CH), IR: νmax (KBr,
cm−1) 1535 and 1609 (C C stret.) 1340 (C N stret.), 790 (C Cl stret.)
710 (C S stret.). 13C NMR δc (DMSO-d6) 123.6, 124.0, 124.6, 125.0,
125.6, 126.3, 127.6, 128.7, 129.3, 130.0, 130.8, 131.2, 132.7, 133.8, 134.9,
138.0, 138.7, 139.3, 139.9, 140.6, 141.2.
2-[(1E)-1-aza-2-(4-hydroxyphenyl)vinyl]-4-
(9-chloroacridin-2-yl)-1,3-thiazole (5b)
M.p. 193–194◦C, Yield 39%, anal. calcd. for C23H14ClN3OS: C 66.42,
1
H 3.39, N 10.10; found C 66.31, H 3.33, N 10.15. H NMR δH (DMSO-
d6, 300 MHz) 6.81–7.73 (12H,m, Ar H), 6.02 (1H,s, N CH), 4.72 (1H,
s, OH). IR: νmax (KBr, cm−1) 1533 and 1612 (C C stret.) 1341 (C N
stret.) 3127 (O H stret.) 795 (C Cl stret.) 712 (C S stret.). 13C NMR δc
(DMSO-d6) 123.5, 124.1, 124.5, 125.1, 125.4, 126.2, 127.7, 128.8, 129.4,
130.2, 130.9, 131.3, 132.8, 133.9, 134.5, 138.2, 138.4, 139.2, 139.4, 140.4,
141.3.
2-[(1E)-1-aza-2-(4-methoxyphenyl)vinyl]-4-
(9-chloroacridin-2-yl)-1,3-thiazole (5c)
M.p. 179–180◦C, Yield 41%, anal. calcd. for C24H16ClN3OS: C 67.05,
1
H 3.75, N 9.77; found C 67.11, H 3.83, N 9.90. H NMR δH (DMSO-
d6, 300 MHz) 6.81–7.77 (12H,m, Ar H), 6.05 (1H,s, stret.), 3128 (O H
stret.), 791 (C Cl stret.), 716 (C S stret.), 559 (C-Br stret.). 13C NMR δc

2200
N. A. Patel et al.
56.3, 123.6,124.2, 124.6, 125.3, 125.6, 126.1, 127.5, 128.7, 129.3, 130.1,
130.4, 131.5, 132.7, 133.6, 134.2, 138.4, 138.6, 139.4, 139.3, 140.1, 141.2.
2-[(1E)-1-aza-2-(3-nitrophenyl)vinyl]-4-(9-chloroacridin-2-yl)-1,
3-thiazole (5d)
M.p. 205–206◦C, Yield 37%, anal. calcd. for C23H13ClN4O2S: C 62.09,
H 2.94, N 12.59; found C 62.01, H 2.43, N 12.46. 1H NMR δH (DMSO-d6,
300 MHz) 6.70–7.70 (12H, m, Ar H), 6.06 (1H,s, N CH). IR: νmax (KBr,
cm−1) 1539 and 1616 (C C stret.), 1354 and 1536 (NO2 stret.), 1346
(C N stret.) 793 (C Cl stret.) 706 (C S stret.). 13C NMR δc (DMSO-d6)
123.2, 124.3, 124.4, 125.7, 125.8, 126.2, 127.4, 128.2, 129.7, 130.3, 130.1,
131.8, 132.4, 133.3, 134.1, 138.4, 138.5, 139.7, 139.2, 140.6, 141.1.
2-[(1E)-1-aza-2-(phenyl)vinyl]-4-(7-bromo-9-
chloroacridin-2-yl)-1,3-thiazole (5e)
M.p. 214–215◦C, Yield 44%, anal. calcd. for C23H13BrClN3S: C 57.69,
H 2.73, N 8.77; found C 57.56, H 2.63, N 8.60. 1H NMR δH (DMSO-d6,
300 MHz) 6.83–7.69 (11H, m, Ar H), 6.07 (1H,s, N CH), IR: νmax (KBr,
cm−1) 1530 and 1611 (C C stret.) 1341 (C N stret.), 796 (C Cl stret.),
555 (C Br stret.), 712 (C S stret.). 13C NMR δc (DMSO-d6) 123.2, 124.2,
124.5, 125.6, 125.8, 126.4, 127.4, 128.9, 129.6, 130.4, 130.1, 131.3, 132.4,
133.7, 134.5, 138.6, 138.1, 139.4, 139.6, 140.4, 141.1.
2-[(1E)-1-aza-2-(4-hydroxyphenyl)vinyl]-4-
(7-bromo-9-chloroacridin-2-yl)-1, 3-thiazole (5f)
M.p. 187–188◦C, Yield 41%, anal. calcd. for C23H13BrClN3OS: C
55.83, H 2.64, N 8.49; found C 55.71, H 2.53, N 8.35. 1H NMR δH (DMSO-
d6, 300 MHz) 6.85–7.79 (11H,m, Ar H), 6.07 (1H,s, N CH), 4.78 (1H,
s, OH). IR: νmax (KBr, cm−1) 1534 and 1611 (C C stret.), 1344 (C N
stret.), 3128 (O H stret.), 791 (C Cl stret.), 716 (C S stret.), 559 (C Br
stret.). 13C NMR δc (DMSO-d6) 123.1, 124.2, 124.3, 125.7, 125.8, 126.9,
127.4, 128.5, 129.6, 130.8, 130.2, 131.4, 132.6, 133.2, 134.2, 138.1, 138.4,
139.7, 139.9, 140.8, 141.8.
2-[(1E)-1-aza-2-(4-methoxyphenyl)vinyl]-4-
(7-bromo-9-chloroacridin-2-yl)-1, 3-thiazole (5g)
M.p. 197–198◦C, Yield 43%, anal. calcd. for C24H15BrClN3OS: C
56.55, H 2.97, N 8.25; found C 56.41, H 3.13, N 8.10. 1H NMR δH (DMSO-
d6, 300 MHz) 6.80–7.70 (11H,m, Ar H), 6.02 (1H,s, N CH), 3.78 (3H,
s, OCH3). IR: νmax (KBr, cm−1) 1534 and 1619 (C C stret.), 1355 (C N
stret.) 785 (C Cl stret.), 562 (C Br stret.), 715 (C S stret.). 13C NMR δc
(DMSO-d6) 56.4, 123.4, 124.1, 124.7, 125.2, 125.4, 126.6, 127.1, 128.7,

Benzoic Acid and Thiazoloacridine Derivatives
2201
129.2, 130.3, 130.5, 131.4, 132.6, 133.2, 134.6, 138.5, 138.4, 139.2, 139.4,
140.2, 141.3.
2-[(1E)-1-aza-2-(3-nitrophenyl)vinyl]-4-
(7-bromo-9-chloroacridin-2-yl)-1,3-thiazole (5h)
M.p. 208–209◦C, Yield 39%, anal. calcd. for C23H12BrClN4O2S: C
1
52.74, H 2.30, N 10.69; found C 52.61, H 2.43, N 10.56. H NMR δH
(DMSO-d6, 300 MHz) 6.74–7.71 (11H,m, Ar H), 6.04 (1H,s, N CH).
IR: νmax (KBr, cm−1) 1540 and 1610 (C C stret.), 1355 and 1535 (NO2
stret.), 1345 (C N stret.), 566 (C Br stret.), 794 (C Cl stret.) 710 (C S
stret.). 13C NMR δc (DMSOd6)123.0, 124.4, 125.5, 125.6, 126.1, 127.3,
128.5, 129.1, 130.4, 130.7, 131.9, 132.2, 133.1, 134.6, 138.5, 138.1, 139.2,
139.3, 140.1, 141.4.
2-[(1E)-1-aza-2-(phenyl)vinyl]-4-
(7-nitro-9-chloroacridin-2-yl)-1,3-thiazole (5i)
M.p. 202–203◦C, Yield 40%, anal. calcd. for C23H13ClN4O2S: C
1
62.09, H 2.94, N 12.59; found C 62.16, H 2.83, N 12.47. H NMR δH
(DMSO-d6, 300 MHz) 6.85–7.60 (11H,m, Ar H), 6.02 (1H,s, N CH),
IR: νmax (KBr, cm−1) 1534 and 1618 (C C stret.), 1348 (C N stret.), 798
(C Cl stret.) 714 (C S stret.), 1525 and 1330 (NO2stret.). 13C NMR
δc (DMSOd6)123.2,124.1, 124.3, 125.8, 125.7, 126.9, 127.5, 128.6, 129.4,
130.2, 130.3, 131.4, 132.4, 133.3, 134.8, 138.2, 138.4, 139.6, 139.7, 140.4,
141.1.
2-[(1E)-1-aza-2-(4-hydroxyphenyl)vinyl]-4-
(7-nitro-9-chloroacridin-2-yl)-1,3-thiazole (5j)
M.p. 193–194◦C, Yield 41%, anal. calcd. for C23H13ClN4O3S: C 59.93,
1
H 2.84, N 12.15; found C 59.81, H 2.73, N 12.27. H NMR δH (DMSO-
d6, 300 MHz) 6.82–7.78 (11H,m, Ar H), 6.06 (1H,s, N CH), 4.77 (1H,
s, OH). IR: νmax (KBr, cm−1) 1534 and 1611 (C C stret.), 1340 (C N
stret.), 3130 (O H stret.), 785 (C Cl stret.), 1524 and 1326 (NO2 stret.),
722 (C S stret.). 13C NMR δc (DMSO-d6) 123.2, 124.6, 124.2, 125.6,
125.5, 126.2, 127.1, 128.4, 129.5, 130.6, 130.9, 131.5, 132.5, 133.3, 134.8,
138.1, 138.6, 139.4, 139.3, 140.5, 141.1.
2-[(1E)-1-aza-2-(4-methoxyphenyl)vinyl]-4-
(7-nitro-9-chloroacridin-2-yl)-1,3-thiazole (5k)
M.p. 189–190◦C, Yield 39%, anal. calcd. For C24H15ClN4O3S: C 60.69,
H 3.18, N 11.79; found C 60.55, H 3.06, N 11.69. 1H NMR δH (DMSO-d6,
300 MHz) 6.80–7.77 (11H, m, Ar H), 6.05 (1H, s, N CH), 3.70 (3H, s,
OCH3). IR: νmax (KBr, cm−1) 1536 and 1611 (C C stret.), 1344 (C N
stret.) 794 (C Cl stret.) 703 (C S stret.). 13C NMR δc (DMSO-d6) 56.2,

2202
N. A. Patel et al.
123.5, 124.3, 124.5, 125.7,125.9, 126.4, 127.2, 128.3, 129.4, 130.4, 130.5,
131.6, 132.4, 133.6, 134.6, 138.2, 138.5, 139.1, 139.6, 140.2, 141.3.
2-[(1E)-1-aza-2-(3-nitrophenyl)vinyl]-4-
(7-nitro-9-chloroacridin-2-yl)-1,3-thiazole (5l)
M.p. 216–217◦C, Yield 37%, anal. calcd. for C23H12ClN5O4S: C 56.39,
H 2.46, N 14.29; found C 56.31, H 2.33, N 12.36. 1H NMR δH (DMSO-d6,
300 MHz) 6.78–7.82 (11H,m, Ar H), 6.04 (1H,s, N CH). IR: νmax (KBr,
cm−1) 1532 and 1615 (C C stret.), 1352 and 1534 (NO2 stret.), 1342
(C N stret.) 791 (C Cl stret.) 704 (C S stret.). 13C NMR δc (DMSO-d6)
123.1, 124.2, 124.4, 125.7, 125.4, 126.2, 127.1, 128.7, 129.8, 130.4, 130.2,
131.4, 132.1, 133.7, 134.2, 138.5, 138.6, 139.2, 139.8, 140.5, 141.6.
CONCLUSION
Some new 2-((4-[2-((1E)-1-aza-2- (substituted phenyl) vinyl) 1, 3-
thiazol-4-yl] phenyl) amino)-5-substituted benzoic acid derivatives
(4a-l), 2-[(1E)-1-aza-2- (substituted phenyl) vinyl]-4-(7-substituted-9-
chloroacridin-2-yl)-1,3-thiazole(5a-l) were synthesized and screened for
their antibacterial and antifungal activity. The antimicrobial study re-
vealed that compounds 4a, 4b, 4c, 4j, 5a, 5i, and 5l show excellent an-
tibacterial activity against the tested organism E coli. Further, all the
synthesized compounds show significant activity against the tested fun-
gus species.
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