Synthesis, characterization, and antimicrobial evaluation of novel trichalcones containing core s-triazine moiety

Article abstract of DOI:10.1007/s00044-013-0837-4

A series of ten new trichalcones containing core s-triazine moiety were synthesized. The intermediate 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine was synthesized by the reaction of cyanuric chloride with sodium salt of p-hydroxy benzaldehyde using phase-transfer catalyst. Thus, the prepared 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine has been subsequently treated with various acetophenones to afford title compound in excellent yields. The structures of intermediate and newly synthesized trichalcones were confirmed by physical and spectral analysis. All the trichalcones were evaluated for antibacterial and antifungal activities. Selected trichalcones showed good to excellent antibacterial and antifungal activities with reference to the well-established standards. Springer Science+Business Media 2013.

Full text of DOI:10.1007/s00044-013-0837-4

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res (2014) 23:2633–2638
DOI 10.1007/s00044-013-0837-4
ORIGINAL RESEARCH
Synthesis, characterization, and antimicrobial evaluation of novel
trichalcones containing core s-triazine moiety
•
Firdous G. Khan Manjusha V. Yadav
•
Ashok D. Sagar
Received: 15 July 2013 / Accepted: 7 October 2013 / Published online: 29 October 2013
Ó Springer Science+Business Media New York 2013
Abstract A series of ten new trichalcones containing
core s-triazine moiety were synthesized. The intermediate
2,4,6-tris(p-formylphenoxy)-1,3,5-triazine was synthesized
by the reaction of cyanuric chloride with sodium salt of
p-hydroxy benzaldehyde using phase-transfer catalyst.
Thus, the prepared 2,4,6-tris(p-formylphenoxy)-1,3,5-tri-
azine has been subsequently treated with various acetoph-
enones to afford title compound in excellent yields. The
structures of intermediate and newly synthesized trichal-
cones were confirmed by physical and spectral analysis. All
the trichalcones were evaluated for antibacterial and anti-
fungal activities. Selected trichalcones showed good to
excellent antibacterial and antifungal activities with refer-
ence to the well-established standards.
possesses a serious challenge to the medical community
and need for an effective therapy has led to the research for
novel antibacterial agents (Akbas and Ismet, 2005). 1,3,5-
Triazine derivatives have been known for long time. They
have found widespread applications in the pharmaceutical,
textile, plastic, and rubber industries and are used as pes-
ticides, dyestuffs, optical bleaches, explosives, and surface
active agents. The chemistry of this group of compounds
has been studied intensively and has been the subject of
many reviews (Smolin and Rapopart, 1959; Mur, 1964;
Quirke, 1984; Bartholomew, 1996; Comins and O’Conner,
1988; Giacomelli et al., 2004). The s-triazine scaffold
provides the basis for the design of biologically relevant
molecules with widespread application as therapeutics and
herbicides (LeBaron et al., 2008). Numerous 1,3,5-triazine
containing compounds are recognized to be powerful
chelating agents and have been used for the preparation of
metal complexes (Gamez et al., 2003) and liquid crystals
(Lai et al., 2008). s-Triazine derivatives have been
employed in combinatorial and supramolecular chemistry
(Giacomelli et al., 2004). s-Triazine derivatives have been
successfully utilized as reagents in the conversion of
functional groups (Blotny, 2006). More recently, triazine
derivatives are involved in new developments in the field
of dendrimers (Steffensen et al., 2006).
Keywords 2,4,6-Trichloro-1,3,5-triazine (TCT) ꢀ
2,4,6-Tris(p-formylphenoxy)-1,3,5-triazine ꢀ Trichalcones ꢀ
Antibacterial activity ꢀ Antifungal activity
Introduction
Research on new substances possessing antibacterial
activity has attracted considerable attention owing to the
continuous increase in bacterial resistance (Witte, 1999).
Further, infection caused by various microorganisms
The reactivity of functional groups on the substituents
attached to the 1,3,5-triazine ring system also has drawn
considerable interest. Recently, the reactivity of peripheral
functional groups on the aryl substituents appended on
s-triazine AB2 type monomer structural units is utilized in the
synthesis of hyperbranched polymers (Kim et al., 1996; Cho
et al., 2001). Though the synthesis of 2,4,6-tris(4-formyl-
phenoxy)-1,3,5-triazine is reported, (Deborah et al., 1994;
Hongdong Duan et al., 2011) the reactivity of its peripheral
trifunctional groups is not much more explored. We are
Electronic supplementary material The online version of this
article (doi:10.1007/s00044-013-0837-4) contains supplementary
material, which is available to authorized users.
F. G. Khan ꢀ M. V. Yadav ꢀ A. D. Sagar (&)
School of Chemical Sciences, Swami Ramanand Terth
Marathwada University, Dnyanteerth, Vishnupuri,
Nanded 431606, Maharashtra, India
e-mail: sagaradd@gmail.com
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Med Chem Res (2014) 23:2633–2638
interested in the studies of three reactive aldehyde groups of
2,4,6-tris(4-formylphenoxy)-1,3,5-triazine for the formation
of trichalcone which later used for biological applications.
The s-triazine-based chalcones and their derivatives are
found to be effective as local anesthetics (Daukshas et al.,
1984), antibacterial (Bremner and Meyer, 1998; Nielsen
et al., 2004), antimalarial (Kenyon et al., 1995; Liu et al.,
2001; Go et al., 2004), antiprotozoal (Zhai et al., 1999; Lu-
nardi et al., 2003), antitubercular (Lin et al., 2002;), anti-
cancer (Modzelewska et al., 2006; Rao et al., 2004), and
antifungal agents (Svetaz et al., 2004; Nowakowska, 2007).
Based on the above observations and earlier investiga-
tions, here we are reporting the synthesis of various tri-
chalcones containing core s-triazine ring and evaluation of
their antibacterial and antifungal activity.
catalyst were added with constant stirring. The stirring was
continued further at the same temperature for 24 h. After
the completion of reaction as monitored by TLC, the two
layers were separated. The organic layer was then well
washed with (10 %) NaOH (3 9 25 mL) and distilled
water (2 9 20 mL). It was dried over anhydrous sodium
sulfate, filtered and the solvent was evaporated under
reduced pressure to yield white powdered product. It was
further purified by recrystallization from ethyl acetate to
afford the white fluffy precipitate (Scheme 1).
Yield (%)-90, m.p(°C)-174, IR (KBr) in cm-1: 2830,
2739 (C–H str. aldehyde), 1702 (C=O), 1566 (C=N str.),
840 (C–N, s-triazine).; 1H NMR (CDCl3): d 7.32 (d, 6HAr-
H), 7.92 (d, 6HAr-H), 10.00 (s, 3H –CHO) ppm. 13C NMR
(CDCl3): d 121.95 (C-3), 130.79 (C-4), 133.88 (C-5),
155.36 (C-2), 172.63 (C-1), 190.61(C-6) ppm.; EIMS (m/z,
%): 442 (M? ?1); Anal. Calcd. for C24H15N3O6: C, 65.31;
H, 3.43; N, 9.52 %. Found: C, 65.29; H, 3.41, N, 9.48 %.
Materials and methods
All reagents were obtained from commercial suppliers,
Merk Pvt. Ltd., Sd Fine Chemicals Mumbai, Aldrich USA
and used without further purification. Melting points were
determined in an open glass capillaries and are uncor-
rected. The purity of compounds was checked by TLC. The
IR spectra of all compounds were recorded in KBr on
Shimadzu FT-IR spectrophotometer. 1H NMR and 13C
NMR spectra (DMSO) were recorded on a Brucker Avance
400 MHz spectrometer using tetramethylsilane (TMS,
d = 0 ppm) as an internal standard. The mass spectra were
recorded on EI-Shimadzu-GC-MS spectrometer.
General procedure for the synthesis of 2,4,6-tris[40-
{100(phenyl)-200-propenone-300-yl}-phenoxy]-1,3,5-
triazineV(a–j)
2,4,6-Tris(4-formyl phenoxy)-1,3,5-triazine(III) (4.42 g,
0.01 mol) was dissolved in DMF (30 mL) and unsubsti-
tuted acetophenone(IV) (3.6 g, 0.03 mol) was added to it.
Then, solution of KOH (5 mL of 40 %) was added to
reaction mixture with constant stirring at room tempera-
ture. After completion of reaction (monitored by TLC,
24 h), the reaction mixture was poured into crushed ice and
neutralized with dil. HCl. The product was precipitated out.
It was separated, washed with water, and dried. It was
purified by recrystallization from the mixture of acetic
acid:water (9:1) to give Va. The same general procedure
was followed for the compound Vb–Vj (Table 1).
Synthesis of 2,4,6-tris (4-formyl phenoxy)-1,3,5-
triazine(III)
A solution of sodium hydroxide (1.6 g, 0.04 mol) and
p-hydroxybenzaldehyde (4.88 g, 0.04 mol) equivalent
amount was prepared in 50 mL distilled water and taken in
a 250 mL round-bottom flask at room temperature. To this
solution, cyanuric chloride (1.84 g, 0.01 mol) in 50 mL
dichloromethane and tetrabutyl ammonium bromide
(TBAB) (0.020 g, 6.5 9 10-5 mol) as phase-transfer
Biological activity
The antimicrobial activities of the synthesized trichalcones
Va–j were determined by disc diffusion method (Biljana
and Niko, 2010). The compounds were evaluated for
CHO
Scheme 1 2,4,6-Tris (4-formyl
phenoxy)-1,3,5-triazine
O
CHO
Cl
OHC
N
N
NaOH(aq.),TBAB
N
N
+
CH2Cl2, R. T., 24 hr
N
O
O
N
Cl
Cl
OH
CHO
I
II
III
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Med Chem Res (2014) 23:2633–2638
2635
period, the plates were examined for the zone of inhibition.
The diameters for the zone of inhibitions were measured
(in mm) including the diameter of the disk also. All
determinations were made in triplicate for each of the
compound and the average value was taken. The antibac-
terial and antifungal activity was evaluated against P.
vulgaris, S. aureus, X. citri, E. cartovora, Alternaria, and
C. lunata. The outcomes of mean values and standard
deviation are shown in Table 2.
Table 1 Synthesis of trichalcones
Entry
Product
R
R1
R2
R3
R4
1.
2.
3.
4.
5.
6.
7.
8
Va
Vb
Vc
Vd
Ve
Vf
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
Cl
H
H
H
Br
H
H
H
NO2
H
H
H
NO2
H
H
H
OCH3
H
H
Vg
Vh
Vi
OCH3
H
H
OCH3
H
OCH3
OCH3
H
OCH3
OCH3
CH3
Spectroscopic data of selected compounds
9.
10.
H
OCH3
H
Vj
H
2,4,6-Tris[40-{100-(phenyl)-200-propenone-300-yl}-
phenoxy]-1,3,5-triazine(Va)
antibacterial activity against Proteus vulgaris, Staphylo-
coccus aureus, Xanthomonas citri, and Erwinia cartovora.
The antifungal activity was evaluated against Alternaria
and Curvularia lunata. The test compounds V(a–j), in
measured quantities, were dissolved in dimethyl sulphox-
ide (DMSO) to get the final concentration 200 lg/mL. The
bacterial (24 h) and fungal (48 h) cultures from the slants
were diluted with sterile distilled water and mixed thor-
oughly to prepare a clear homogeneous suspension. These
suspensions were spread on solidified agar (NA-nutrient
agar for bacteria and PDA-potato dextrose agar for fungi)
medium. The filter paper disks prepared by only DMSO (as
a negative control) and with solutions of test compounds
V(a–j) as well as standard compounds (Penicillin and
Nystatin as positive control) were carefully placed over the
spread cultures and incubated at 37 °C for 24 h for bacteria
and at 28–30 °C for 48 h for fungi. After the incubation
Yield(%)-85, m.p.(°C)-180, IR (KBr) in cm-1:1643 (C=O),
1602 (C=N str.), 1579 (–CH=CH–, str.), 831 (C–N, s-tri-
azine).; 1H NMR (DMSO- d6): d 6.80 to 6.83 (d, 3H, –CO–
CH=), 7.03–7.72 (m, 27 Ar–H), 8.09 to 8.13 (d, 3H, Ar–
CH =) ppm.; 13C NMR (DMSO- d6) d 115.73 (C-3) 118.73
(C-3), 125.49 (C-4), 127.96 (C-10), 128.26 (C-5), 130.33 (C-
12), 132.23 (C-9), 137.99 (C-6), 144.52 (C-2), 160.05 (C-1),
189.16 (C-8) ppm.; Anal. Calcd. for C48H33N3O6: C, 77.10;
H, 4.45; N, 5.62 %. Found: C, 77.05; H, 4.41, N, 5.58 %.
2,4,6-Tris[40-{100-(4000-chlorophenyl)-200-propenone-300-yl}-
phenoxy]-1,3,5-triazine(Vb)
Yield(%)-89, m.p.(°C)-230, IR (KBr) in cm-1: 1688
(C=O), 1599 (C=N str.), 1500 (–CH=CH–, str.), 817 (C–N,
Table 2 Antibacterial and antifungal activities of synthesized trichalcones compounds using disc diffusion method(Va–j)
S. no.
Zone of inhibition (mm)
P. vulgaris
S. aureus
X. citri
E. cartovora
Alternaria
C. lunata
Va
7.83 0.28
14.00 0.10
11.86 0.23
5.90 0.17
10.03 0.05
6.96 0.05
7.86 0.23
12.26 0.25
11.06 0.11
10.03 0.06
15
10.03 0.15
12.06 0.20
9.96 0.05
4.93 0.11
7.13 0.15
7.86 0.23
9.10 0.10
9.90 .0.17
13.03 0.05
7.93 0.11
15
6.96 0.15
10.06 0.11
11.10 0.17
6.10 0.10
7.96 0.05
8.86 0.32
10.03 0.15
11.13 0.15
10.10 0.17
10.06 0.11
15
7.93 0.20
8.06 0.05
13.00 0.10
6.96 0.05
6.00 0.10
8.06 0.11
9.10 0.17
12.16 0.20
12.26 0.25
8.03 0.15
15
5.10 0.10
8.03 0.15
6.16 0.28
7.00 0.10
7.96 0.15
10.23 0.20
12.16 0.20
12.13 0.15
13.20 0.20
5.16 0.05
NA
6.16 0.15
7.20 0.20
10.13 0.11
8.20 0.17
6.96 0.05
13.16 0.15
12.23 0.20
12.13 0.15
14.13 0.05
6.96 0.05
NA
Vb
Vc
Vd
Ve
Vf
Vg
Vh
Vi
Vj
Penicillin (Std.)
Nystatin (Std.)
DMSO -ve control
NA
NA
NA
NA
15
15
–
–
–
–
–
–
P. vulgaris Proteus vulgaris, S. aureus Staphylococcus aureus, X. citri Xanthomonas citri, E. cartovora Erwinia cartovora, C. lunata Curvularia
lunata, NA not applicable
(-) No zone of inhibition, values are means of three replicates, Standard deviation
123

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Med Chem Res (2014) 23:2633–2638
s-triazine).; 1H NMR (DMSO-d6): d 7.3 (d, 3H, –CO–
CH=), 7.6–8.0 (m, 24Ar-H), 8.1 to 8.2 (d, 3H, Ar–CH=)
ppm.;13C NMR (DMSO- d6) d 121.65 (C-3), 121.92 (C-7),
128.48 (C-4), 129.63 (C-11), 129.80 (C-5), 132.49 (C-10),
135.89 (C-9), 138.41 (C-12), 139.02 (C-6), 143.06 (C-2),
168.39 (C-1), 187.82 (C-8) ppm.; Anal. Calcd. for
C48H30Cl3N3O6: C, 67.74; H, 3.55; N, 4.94 %. Found: C,
67.70; H, 3.50., N, 4.52 %.
2,4,6-Tris[40-{100-(3000,4000,5000-trimethoxyphenyl)-200-
propenone-300-yl}-phenoxy]-1,3,5-triazine(Vi)
Yield(%)-84, m.p.(°C)-210, IR (KBr) in cm-1: 1647
(C=O), 1604 (C=N str.), 1570 (–CH=CH–, str.), 1163 (C–
O), 829 (C–N, s-triazine).;1H NMR (DMSO- d6): d 3.7 (s,
9H, OCH3),3.8 (s, 18 H 2 9 OCH3), 6.89–6.92 (d, 3H,
–CO–CH=), 7.20–7.89 (m, 18Ar-H), 8.007–8.10 (d, 3H,
Ar–CH=) ppm.;13C NMR (DMSO- d6): d 55.79 (C-13),
60.12 (C-14,) 105.51 (C-4), 115.11 (C-3), 121.01 (C-8),
129.11 (C-7), 130.28 (C-10), 130.69 (C-9), 139.36 (C-6),
142.92 (C-11), 152.90 (C-2), 161.94 (C-1), 187.19 (C-8).
ppm.; Anal. Calcd. for C57H51N3O15: C, 67.25; H, 5.05; N,
4.13 %. Found: C, 67.23; H, 5.01., N, 4.09 %.
2,4,6-Tris[40-{100-(4000-bromophenyl phenyl)-200-
propenone-300-yl}-phenoxy]-1,3,5-triazine(Vc)
Yield(%)-88, m.p.(°C)-195, IR (KBr) in cm-1: 1688
(C=O), 1602 (C=N str.), 1599 (–CH=CH–, str.), 817 (C–N,
1
s-triazine).; H NMR (DMSO- d6): d 6.57–6.60 (d, 3H,
–CO–CH=), 7.04–7.73 (m, 24 Ar–H), 7.83–7.86 (d, 3H,
Ar–CH=) ppm.;13C NMR (DMSO- d6) d 114.96 (C-3)
121.65 (C-7), 127.93 (C-4), 129.42 (C-11), 131.37 (C-5),
131.48 (C-10), 132.49 (C-9), 135.33 (C-12), 138.41 (C-6),
139.02 (C-2), 155.57 (C-1), 197.29 (C-8) ppm.; Anal.
Calcd. for C48H30Br3N3O6: C, 58.56; H, 3.07; N, 4.27 %.
Found: C, 58.52; H, 3.02., N, 4.22 %.
Results and discussion
The starting material 2,4,6-Tris(p-formylphenoxy)-1,3,5-
triazine(III) for the synthesis of trichalcones(V) was pre-
pared by the reaction of one equivalent of 2,4,6-trichloro-
1,3,5-triazine and three equivalent of sodium salt of
p-hydroxybenzaldehyde in the presence of TBAB as phase-
transfer catalyst in dichloromethane at room temperature
for 24 h. Trichalcones(V) were synthesized by the reaction
of one equivalent of 2,4,6-tris(p-formylphenoxy)-1,3,5-tri-
azine(III) and variety of acetophenones(IV) in the presence
of aqueous KOH solution at room temperature for 24 h
affording good yield. All the newly synthesized trichal-
cones were evaluated for their antibacterial and antifungal
activity.
2,4,6-Tris[40-{100-(4000-nitrophenyl)-200-propenone-300-
yl}-phenoxy]-1,3,5-triazine(Vd)
Yield(%)-85, m.p.(°C)-200, IR (KBr) in cm-1: 1697
(C=O), 1598 (C=N str.), 1521 (–CH=CH–, str.), 817 (C–N,
1
s-triazine).; H NMR (DMSO- d6): d 7.49–7.52 (d, 3H,
–CO–CH=), 7.8–8.29 (m, 24 Ar–H), 8.31–8.32 (d, 3H, Ar–
CH=)ppm.;13C NMR (DMSO- d6) d 121.65 (C-3), 121.92
(C-7), 128.48 (C-4), 129.63 (C-11), 129.80 (C-5), 132.49
(C-10), 135.89 (C-5), 138.41 (C-10), 139.02 (C-9), 143.06
(C-12), 168.39 (C-1), 187.82 (C-8) ppm.; Anal. Calcd. for
C48H30N6O12: C, 65.31; H, 3.43; N, 9.52 %. Found: C,
65.25; H, 3.40., N, 9.48 %.
We have introduced for the first time the use of TBAB
as a phase-transfer catalyst in the synthesis of 2,4,6-tris(p-
formylphenoxy)-1,3,5-triazine at room temperature
affording excellent yield 90 % higher than the published
methods which require refluxing (Deborah et al., 1994;
Hongdong Duan et al., 2011). Initially, trichalcone(Va)
was obtained using synthetic method outlined in Scheme 2
affording good yield. Infrared (IR) indicated the disap-
pearance of aldehyde. Further variety of trichalcones (Vb–
Vj) were synthesized by the similar procedure using array
of substituted acetophenones containing electron-with-
drawing and -releasing substituent to account the effect of
substituent on yield of trichalcone. The electron-with-
drawing and -releasing substituent does not show any
considerable effect on yield of trichalcone.
2,4,6-Tris[40-{100-(4000-methoxyphenyl)-200-propenone-
300-yl}-phenoxy]-1,3,5triazine(Vf)
Yield(%)-86, m.p.(°C)-250, IR (KBr) in cm-1: 1643
(C=O), 1602 (C=N str.), 1577 (–CH=CH–, str.), 1166 (C–
1
O) 829 (C–N, s-triazine).; H NMR (DMSO- d6): d 3.8 (s,
9H, OCH3) 6.79–6.83 (d, 3H, –CO–CH=), 7.03–7.96 (m,
24 Ar–H), 8.09–8.13 (d, 3H, Ar–CH=)ppm.;13C NMR
(DMSO- d6) d 55.14 (C-13), 113.3 (C-11), 121.97 (C-3),
122.17 (C-7), 129.33 (C-4), 130.18 (C-5), 130.48 (C-9),
133.05 (C-10), 141.65 (C-6), 151.38 (C-2), 161.11 (C-12),
163.06 (C-1), 187.35 (C-8) ppm.; Anal. Calcd. for
C51H39N3O9: C, 73.11; H, 4.69; N, 5.02 %. Found: C,
73.05; H, 4.66., N, 5.05 %.
In comparison with standard antibacterial penicillin,
compounds Vb and Vh found to be active against P. vul-
garis. Compounds Vb and Vi were found to be active
against S. aureus. As compared with standard antibacterial
compounds, Vb, Vc, Vh, Vi, and Vj were observed as
active against X. citri and compounds Vc, Vh, and Vi were
found to be active against E. cartovora. In comparison with
123

Med Chem Res (2014) 23:2633–2638
2637
O
R
CHO
R1
R2
COCH3
R
R4
O
R
O
O
N
R4
R3
OHC
R1
R2
KOH, DMF
R.T., 24 hr.
N
N
N
N
+
R4
O
O
O
O
N
O
R3
R1
R3
R2
R
CHO
R1
R2
R4
R3
(Va-j)
III
IV
Scheme 2 Synthesis of 2,4,6-Tris[40-{100(phenyl)-200-propenone-300-yl}-phenoxy]-1,3,5-triazineV(a–j)
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standard antifungal nystatine, compounds Vf, Vg, and Vh
were found to be active against Alternaria and compounds
Vf and Vi were found to be active against C. lunata.
Compound Vb showed highest antibacterial activity
whereas compound Vi showed highest antifungal activity.
Conclusion
In conclusion, we have developed a new method for the
synthesis of intermediate 2,4,6-tris(p-formylphenoxy)-
1,3,5-triazine(III) using phase-transfer catalyst. The reac-
tive terminal aldehyde groups on the side substituents of
2,4,6-tris(p-formylphenoxy)-1,3,5-triazine(III) could be
readily elaborated to the trifunctionalized chalcones by
reaction with the various acetophenones. The structures of
the newly synthesized trichalcones were confirmed by
1
elemental analysis, FT-IR, H and 13C NMR spectroscopy
and further screened for their antimicrobial activity. The
antibacterial and antifungal activity revealed that most of
the compounds showed moderate to good activity.
Efforts on the synthesis, characterization, and antimi-
crobial activity of trichalcones starting from 2,4,6-tris(4-
acetylphenoxy)-1,3,5-triazine are in progress and will be
reported in future communications.
Acknowledgments The authors are thankful to the University Grant
Commission, Government of India for financial assistance for this
research work.
Kenyon R, Li GL, Cohen EF, Chen X, Gong B, Dominguez JN,
Davidson E, Kurzbasn G, Miller RE, Nuzum EO, McKerrowis
JH (1995) In vitro antimalarial activity of chalcones and their
derivatives. J Med Chem 38(26):5031–5037
Kim C, Chang Y, Kim JS (1996) Dendritic hyperbranched polye-
thynylenes with the 1,3,5-s-triazine moiety. Macromolecules
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