Synthesis and antimicrobial studies of novel bis(diamino)thiazoles

Article abstract of DOI:10.1002/jhet.106

(Chemical Equation Presented) The synthesis of novel bis(diamino)thiazoles has been achieved by reacting bis(bromoacetyl)benzene and 1-alkyl(or aryl)-3-(N-nitroamidino)thioureas in presence of triethylamine. These new compounds were characterized by spect

Full text of DOI:10.1002/jhet.106

May 2009
Synthesis and Antimicrobial Studies of Novel
Bis(diamino)thiazoles
455
Sreedharan L. Manju,a* Satyabhama K. C. Devi,b
and Kallikat N. Rajasekharanc
aOrganic Chemistry Division, Vellore Institute of Technology, Vellore, Tamilnadu, India
bDepartment of Chemistry, Jeppiaar Engineering College, Chennai, Tamilnadu, India
cDepartment of Chemistry, University of Kerala, Trivandrum, Kerala 695581, India
*E-mail: girishmanju@gmail.com
Received April 24, 2008
DOI 10.1002/jhet.106
Published online 26 May 2009 in Wiley InterScience (www.interscience.wiley.com).
The synthesis of novel bis(diamino)thiazoles has been achieved by reacting bis(bromoacetyl)benzene
and 1-alkyl(or aryl)-3-(N-nitroamidino)thioureas in presence of triethylamine. These new compounds
were characterized by spectral analysis and screened for antimicrobial activities.
J. Heterocyclic Chem., 46, 455 (2009).
INTRODUCTION
ing the [C4AN3AC2AS1] ring atoms for the thiazole
ring construction, the remaining C5 carbon of the thia-
zole being sourced from a reactive halomethyl com-
pound of the type XACH2AEWG where the electron
withdrawing group EWG can be O2NAC6H4A, NCA,
RACOA, ROACOA, ArACH¼¼CHACOA or similar
ones, including a-haloketones. This [4 þ 1] ring assem-
bly, in a tandem bromination-cyclization strategy has
been now applied for the synthesis of novel [4-(4-
amino-2-(N-substituted amino)thiazole-5-carbonyl)-phe-
nyl]-(4-amino-2-(N-substituted amino)thiazol-5-yl)-meth-
anones. The above [(C4AN3AC2AS1) þ C5] ring assem-
bly of 2,4-diaminothiazole using functionalized thiourea
derivatives is distinctly different from the classic
Hantzsch synthesis, which is the synthesis of 2-amino-
thiazoles from halo carbonyl compounds and thioureas
is well reviewed [10,11] in literature. The latter is a [3
þ 2] ring construction strategy starting from simple thi-
oureas, that give the [N3AC2AS1] ring atoms, and a-
haloketones, which provide the remaining [C4AC5]
atoms, giving 2-aminothiazoles as products.
Compounds that incorporate two thiazole rings either
directly connected as in bithiazoles or through a linker
unit as in bisthiazolyl compounds, show significant bio-
logical activity. Bleomycin, isolated from Streptomyces
verticilus containing a bithiazole moiety, which has
been shown to bind to DNA thereby inhibiting DNA
synthesis of the tumor cells, is the prime example for
such compounds [1]. A number of other bi- or bisthia-
zoles [2–4] exhibit antibacterial, antiviral and cytotoxic
activities. In addition to these compounds, quite a few
of the highly active secondary metabolites from marine
tunicates also contain bisthiazole units [5]. It also
appears that the thiazole units need not always be
directly linked for the manifestation of bioactivity; for
example, ritonavir, a bisthiazole in which the two thia-
zole units are separated by a small peptidomimetic
chain, is a potent bisthiazole HIV-protease inhibitor [6].
As far back as in 1997, we have observed that 2,4-
diamino-5-ketothiazoles show excellent cytotoxic activ-
ity [7] based on screening programs at National Cancer
Institute, an observation later substantiated further by us
[8]. As part of our work in the synthesis of 2,4-diamino-
5-ketothiazoles, we have developed a variety of thiourea
based synthons, such as amidinothioureas, nitroamidino-
thioureas, and thiocarbamoylamidinopyrazoles that [9]
serve as precursors for 2,4-diaminothiazoles by provid-
RESULTS AND DISCUSSION
In a typical case, the reaction of 1-(N-nitroamidino)-
3-n-propylthiourea with 1,4-bis(bromoacetyl)benzene
C
V
2009 HeteroCorporation

456
S. L. Manju, S. K. C. Devi, and K. N. Rajasekharan
Vol 46
Scheme 1
was done in DMF in the presence of triethylamine at
80–85ꢀC for 15 min to obtain a compound which had a
molecular composition C20H24N6O2S2 gave a product
the FAB mass spectrum of the which showed a MHþ
peak at m/z 445 indicating that the molecular mass of
the compound is 444. It’s 1H NMR spectrum showed
the presence of an n-propylamino group, a phenylene
group and NH hydrogen. The 13C NMR spectrum
showed three peaks in the alkyl region at 13.51, 20.12,
and 31.50 ppm indicating the presence of the n-propyl
group. The signals at 143.8, 156.7, and 167 ppm were
assignable to thiazole ring carbons, that at 181 ppm to
carbonyl carbon and those at 126.4, 127.6, 128, and 129
ppm, to a p-phenylene group carbons. Accordingly, the
compound was formulated as [4-(4-amino-2-n-propyla-
minothiazole-5-carbonyl)phenyl]-(4-amino-2-n-propyla-
minothiazol-5-yl)methanone 3a. The reaction was
next extended to 1-aryl-3-(N-nitroamidino)thioureas. As
a typical example, 1-(4-methylphenyl-3-(N-nitroamidi-
no)thiourea reacted with 1,4-bis(bromoacetyl)benzene
bonyl)phenyl]-(4-amino-2-(N-substituted amino)thiazol-
5-yl)methanones (3a–j) were screened for their antibac-
terial and antifungal activities. The data from these stud-
ies are compiled in Table 1.
In conclusion, we have described an efficient syn-
thetic route to obtain bis(diamino)thiazoles (3a–j), sev-
eral of which show good antibacterial and antifungal
activities.
EXPERIMENTAL
Melting points were determined by open capillary method
and were uncorrected. The IR spectra were recorded in potas-
sium bromide pellets with an AVATAR 330 FTIR spectrome-
ter and the 1H, 13C NMR experiments were done on AMX-
400/DRX-500 NMR spectrometers. The molecular masses of
compounds were confirmed by taking EI and the fast atom
bombardment mass spectra (FAB-MS). The compounds were
purified by column chromatography using silica gel (60–120
mesh, E. Merck). The required alkyl and aryl isothiocyanates
and nitroamidinothioureas were synthesized by reported meth-
ods [9(c),12] The bromination of 2,4-diacetylbenzene was
done in DMF at 80–85ꢀC and the 1,4-bis(bromoacetyl)benzene
1 was isolated and characterized. The antibacterial and antifun-
gal activities were studied by the disc diffusion method against
Staphylococcus aureus, Klebsiella pneumonia, Candida albi-
cans, and Aspergillus niger. In the case of C. albicans and
A. niger the standard used is ketoconazole and in the case of
S. aureus and K. pneumonia the data has been compared with
ciplofloxacin.
to give
a compound with molecular composition
C28H24N6O2S2. The 1H NMR spectrum of the com-
pound showed a doublet due to four hydrogens at d
7.02–7.25, assignable to aryl hydrogen ortho- to a NH
group. Another doublet of four hydrogens at d 7.35–
7.55 was ascribed to the aryl hydrogen meta- to a NH
group. A singlet of four hydrogens at d 7.74 was attrib-
utable to the aryl hydrogen of a p-phenylene group. A
broad peak at d 8.0–8.52 was due to NH hydrogen. A
singlet due to two hydrogens at d 10.72 was also assign-
able to two NH groups. The 13C NMR spectrum showed
fourteen peaks among which the peak at d 26.98 showed
the presence of a methyl group. Based on these data and
the fragmentations observed in its EI mass spectrum, the
compound was assigned the structure [4-(4-amino-4-phe-
nylaminothiazole-5-carbonyl)phenyl]-(4-amino-4-phenyl-
aminothiazol-5-yl)methanone 3j (Scheme 1).
Bis(bromoacetyl)benzene (1). To a solution of 1,4-diacetyl-
benzene (0.21 g, 1.3 mmol) in glacial acetic acid, bromine
(2.6 mmol, 90 mL) in glacial acetic acid (2 mL) was added
slowly and warmed. The reaction mixture was then heated at
95ꢀC for 1 h, and then poured into ice water and the product
was filtered, dried and recrystallized from glacial acetic, to
obtain colorless shinning crystals of 1,4-bis(bromoacetyl)ben-
zene (1) in 65% yield, mp 165–167ꢀC; IR (KBr): 2998, 2945,
1699, 1402, 1263, 1202, 1121, 987, 811, 683, 565, 499 cmꢁ1
;
1H NMR (400 MHz, CDCl3): d: 4.45 (s, 4H, CH2), 8.04–8.10
(m, 4H, ArAH); FAB ms: m/z (MHþ) 320.
The general reaction scheme is depicted above. These
new [4-(4-amino-2-(N-substituted amino)thiazole-5-car-
1-t-Butyl-3-(N-nitroamidino)thiourea (2c). Finely pow-
dered potassium hydroxide (1.08 g, 1.92 mmol) was added to
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

May 2009
Synthesis and Antimicrobial Studies of Novel Bis(diamino)thiazoles
457
Table 1
Antimicrobial activity studies of compounds (3a-j) by disc diffusion method.
Zone of inhibition (mm)
Bacterial strain
Fungal strain
S. aureus
Sample
K. pneumonia
Sample
C. albicans
Sample
A. niger
Sample
Compound
Std
Std
Std
Std
3a
3b
3c
3d
3e
3f
3g
3h
3i
29
27
28
22
26
28
27
29
27
29
17
22
18
21
18
23
20
20
24
19
28
33
31
30
32
33
32
32
32
32
19
19
22
20
20
17
23
27
22
26
29
33
32
31
33
31
32
33
32
33
19
22
18
19
21
20
19
22
19
21
26
24
23
19
23
21
20
24
22
23
13
19
19
16
19
13
17
19
17
18
3j
Concentration: l00 lg/mL.
a solution of nitroguanidine (1 g, 9.6 mmol) in N,N-dimethyl-
formamide (10 mL) and this mixture was stirred for 15 min.
To this, t-butyl isothiocyanate (9.6 mmol) in N,N-dimethylfor-
mamide (5 mL) was added in 15 min and the stirring was con-
tinued for another 60 min. The reaction mixture was then
poured onto crushed ice and the mixture was acidified with
dilute hydrochloric acid (0.1N). The precipitated compound
was filtered, dried and crystallized from ethanol to obtain 1-t-
butyl-3-(N-nitroamidino)thiourea (2c) in 71% yield, mp 146–
148ꢀC; IR (KBr) 3353, 3284, 2983, 2934, 2545, 1715, 1647,
1608, 1545, 1365, 1259,1191,1076, 957, 786, 705, 632
cmꢁ1,1H NMR (400 MHz, DMSO-d6): d 1.4 (s, 9H, CH3),
9.10–9.45 (br s, 1H, NH), 9.66 (s, 1H, NH), 9.96 (s, 1H, NH);
FAB ms: m/z (MHþ) 220. Anal. Calcd. for C6H13N5O2S: C,
32.86; H, 5.98; N, 31.94%. Found: C, 33.00; H, 6.09; N,
31.81%.
General procedure for the synthesis of bis(diamino)thia-
zoles (3a–j). To a solution of 1,4-bis(bromoacetyl)benzene in
DMF (2 mL) kept at 50–60ꢀC containing triethylamine (2
mmol), 1-alkyl/aryl-3-(N-nitroamidino)thioureas (1 mmol), in
N,N-dimethylformamide (2 mL) was added dropwise. After
warming for 15 min, the reaction mixture was poured into
water. The product obtained, after adjusting the pH to 7, was
collected and purified using column chromatography using
silica gel by elution using chloroform-ethyl acetate (1:5) to
obtain the bisthiazoles in 65–80% yield.
pound was obtained as yellow-colored microcrystals (60%), mp
> 250ꢀC; IR (KBr): 3347, 2958, 2926, 2857, 1703, 1592, 1518,
1463, 1407, 1261, 1229, 1097, 801, 732, 567 cmꢁ1 1H NMR
;
(400 MHz, DMSO-d6): d 0.72 (t, 6H, CH3),1.32 (m, 4H, CH2, J
¼ 7 Hz), 1.40–1.60 (q, 4H, CH2), 3.72 (t, 4H, CH2), 7.40–8.30
(m, 4H, ArAH), 8.6 (br s, 1H, NH); 13C NMR (100 MHz,
DMSO-d6): d 12.11, 13.53, 19.46, 30.52, 126.64, 126.92,
128.55, 129.30, 143.8, 156.66, 168, 179, 180ppm; FAB ms: m/z
(MHþ) 473. Anal. Calcd. for C22H28N6O2S2: C, 55.91; H, 5.97;
N, 17.78%. Found: C, 55.85; H, 5.92; N, 17.69%.
[4-(4-Amino-2-t-butylaminothiazole-5-carbonyl)phenyl]-(4-
amino-2-t-butylaminothiazol-5-yl)methanone (3c). This com-
pound was obtained as yellow-colored microcrystals (55%),
mp > 250ꢀC; IR (KBr): 3281, 2970, 2929, 1685, 1603, 1557,
1
1437, 1367, 1275, 1200, 1096, 905, 851, 749 cmꢁ1; H NMR
(400 MHz, DMSO-d6): d 1.35 (s, 18H, CH3), 7.6–8.5 (m, 4H,
ArAH); 13C NMR (100 MHz, DMSO-d6): d 27.34, 28.17,
29.05, 52.39, 126.40, 126.60, 128.04, 129.31, 143.28, 156.31,
166.32, 169.27, 179.74, 180.41 ppm; FAB ms: m/z (MHþ)
473. Anal. Calcd. for: Found: C, 55.89; H, 5.91; N, 17.82%;
Calculated for C22H28N6O2S2: C, 55.91; H, 5.97; N, 17.78%.
[4-(2-Allylamino-4-aminothiazole-5-carbonyl)phenyl]-(2-
allylamino-4-aminothiazol-5-yl)methanone (3d). This com-
pound was obtained as yellow-colored microcrystals (48%),
mp > 250ꢀC; IR (KBr): 3440, 2925, 1608, 1566, 1446, 1384,
1309, 1226, 1091, 929, 581 cmꢁ1 1H NMR (400 MHz,
;
[4-(4-Amino-2-n-propylaminothiazole-5-carbonyl)phenyl]-
(4-amino-2-n-propylaminothiazol-5-yl)-methanone (3a). This
compound was obtained as yellow-colored microcrystals
(65%), mp > 250ꢀC; IR (KBr): 3416, 2963, 2928, 1603, 1567,
DMSO-d6): d 3.70–4.10 (m, 4H, CH2), 4.9–5.4 (m, 4H, CH2),
5.70–6.00 (m, 2H, CH), 7.6–8.2 (m, 4H, ArH); 13C NMR (100
MHz, DMSO-d6): d 28.81, 46.8, 54.8, 72.15, 92.6, 116.2,
118.37, 166.6, 180.1, 193.6 ppm; FAB ms: m/z (MHþ) 441.
Anal. Calcd. for C20H20N6O2S2: C, 54.52; H, 4.58; N, 19.08%.
Found: C, 54.43; H, 4.44; N, 19.18%
1
1444, 1384, 1279, 1225, 1091, 747 cmꢁ1; H NMR (300 MHz,
DMSO-d6): d 0.85 (t, 6H, CH3, J ¼ 7 Hz), 1.53 (sextet, 4H,
CH2, J ¼ 7 Hz), 3.68 (t, 4H, CH2, J ¼ 5.1 Hz), 7.60–8.10 (m,
4H, ArAH), 8.69 (s, NH); 13C NMR (100 MHz, DMSO-d6)d:
13.51, 20.12, 31.50, 126.4, 127.6, 128, 129, 143.8, 156.7, 167,
181 ppm; FAB ms: m/z (MHþ) 445. Anal. Calcd. for
C20H24N6O2S2: C, 54.03; H, 5.44; N, 18.91%. Found: C,
54.00; H, 5.40; N, 18.81%.
[4-(4-amino-2-n-benzylaminothiazole-5-carbonyl)phenyl]-
(4-amino-2-n-benzylaminothiazol-5-yl)methanone (3e). This
compound was obtained as yellow-colored microcrystals
(51%), mp > 250ꢀC; IR (KBr): 3409, 2958, 2927, 1703, 1581,
1518, 1464, 1407, 1230, 1103 cmꢁ1 1H NMR (400 MHz,
;
DMSO-d6): d 4.5 (s, 2H, CH2), 7.1–8.1 (m, ArAH); 13C NMR
(100 MHz, DMSO-d6): d 47, 48, 126, 127, 128, 129, 137.7;
FAB ms: m/z (MHþ) 541. Anal. Calcd. for C28H24N6O2S2: C,
[4-(4-Amino-2-n-butylaminothiazole-5-carbonyl)phenyl]-(4-
amino-2-n-butylaminothiazol-5-yl)methanone (3b). This com-
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458
S. L. Manju, S. K. C. Devi, and K. N. Rajasekharan
Vol 46
62.20; H, 4.47; N, 15.55%. Found: C, 62.28; H, 4.54; N,
15.32%.
{4-[4-Amino-2-(4-methylphenylamino)thiazole-5-carbonyl]-
phenyl}-[4-amino-2-(4-methylphenylamino)thiazol-5-yl]metha-
none (3j). This compound was obtained as yellow-colored
microcrystals (52%), mp > 250ꢀC; IR (KBr): 3445, 3221,
[4-(4-Amino-2-phenylaminothiazole-5-carbonyl)phenyl]-(4-
amino-2-phenylaminothiazol-5-yl)methanone (3f). This com-
pound was obtained as yellow-colored microcrystals (42%),
mp > 250ꢀC; IR (KBr): 3435, 2360, 1659, 1598, 1549, 1440,
890, 853, 780, 743, 698 cmꢁ1;1H NMR (400 MHz, DMSO-
d6): d 7.05 (t, 2H, 2ArAH), 7.31(t, 4H, 4ArAH), 7.58 (d, 4H,
4ArAH), 7.67–7.81(m, 8H, 4ArAH, 2NH2); 13C NMR (100
MHz, DMSO-d6): d 93.14, 119.51, 123.66, 127.18, 129.27,
139.93, 143.74, 166.38, 167.92, 182.16 ppm; FAB ms: m/z
(MHþ) 513; Anal. Calcd. for C26H20N6O2S2: C, 60.92; H,
3.93; N, 16.40%. Found: C, 60.75; H, 3.81; N, 16.30%.
{4-[4-Amino-2-(4-chlorophenylamino)thiazole-5-carbonyl]-
phenyl}-[4-amino-2-(4-chlorophenylamino)thiazol-5-yl]metha-
none (3g). This compound was obtained as yellow-colored
microcrystals (42%), mp > 250ꢀC; IR (KBr): 3430, 2360,
2358, 1551, 1423, 1167, 1076, 892, 850, 770, 741, 690 cmꢁ1
;
1H NMR (300 MHz, DMSO-d6): d 2.60 (s, 6H, CH3), 7.02–
7.25 (d, 4H, J ¼ 6.49 Hz), 7.35–7.55 (d, 4H, J ¼ 6.52 Hz),
7.74 (s, 4H), 8.0–8.52 (br, 4H, NH2), 10.72 (s, 2H), 13C NMR
(100 MHz, DMSO-d6): d 26.98, 93.76, 117.98, 119.76, 123.91,
127.35, 128.41, 129.21, 138.01, 139.59, 146.05, 166.50,
168.65, 182.03 ppm; El ms: m/z (%) 149 (34), 147 (8), 133
(10), 107 (64), 106 (38), 91 (100). Anal. Calcd. for
C28H24N6O2S2: C, 62.22; H, 4.47; N, 15.55%. Found: C,
62.14; H, 4.39; N, 15.29%.
REFERENCES AND NOTES
1
1598, 1530, 1492, 1426, 1091, 825, 668 cmꢁ1; H NMR (400
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ms: m/z (%) 453 (2), 411 (2), 224 (11),184 (4), 169 (26), 153
(11), 152 (20), 127 (100), 111 (48). Anal. Calcd. for
C26H18Cl2N6O2S2: C, 53.70; H, 3.12; N, 14.45%. Found: C,
53.55; H, 3.09; N, 14.32%.
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2361, 1552, 1422, 1167, 1088, 898, 850, 781, 745, 693 cmꢁ1
;
1H NMR (250 MHz, DMSO-d6): d 2.65 (s, 6H, CH3), 6.98–
7.2 (d, 4H, J ¼ 6.38 Hz), 7.29–7.45 (d, 4H, J ¼ 6.43 Hz),
7.75 (s, 4H); 13C NMR (100 MHz, DMSO-d6): d 26.82, 94.47,
117.34, 120.97, 125.49, 127.44, 128.34, 129.16, 138.07,
138.90, 139.34, 145.83, 165.87, 169.64, 182.80 ppm; FAB ms:
m/z (MHþ) 541. Anal. Calcd. for C28H24N6O2S2: C, 62.22; H,
4.47; N, 15.55%. Found: C, 62.17; H, 4.52; N, 15.29%.
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{4-[4-Amino-2-(4-ethoxyphenylamino)thiazole-5-carbonyl]-
phenyl}-[4-amino-2-(4-ethoxyphenylamino)thiazol-5-yl]metha-
none (3i). This compound was obtained as yellow-colored
microcrystals (35%), mp > 250ꢀC; IR (KBr): 3483, 3311,
3306, 3275, 2996, 1591, 1510, 1428, 1235, 1180, 1092, 1035,
822, 746 cmꢁ1 1H NMR (400 MHz, DMSO-d6): d 1.39 (t,
;
6H, CH3), 4.02 (q, 4H, CH2), 6.86 (d, ArAH), 7.30–7.50 (m,
ArAH), 7.73 (s, ArAH), 7.94 (s, ArAH), 10.40 (s, NH2); 13C
NMR (100 MHz, DMSO-d6): d 14.30, 62.83, 114.24, 121.16,
126.34 ppm; FAB ms: m/z (MHþ) 601. Anal. Calcd. for
C30H28N6O4S2: C, 59.98; H, 4.70; N, 13.99%. Found: C,
59.78; H, 4.61; N, 13.73%.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet