Synthesis and Antimicrobial Activities of Some 3-Phenanthryl Chalcones

Full text of DOI:10.1080/00304948.2018.1468990

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
ISSN: 0030-4948 (Print) 1945-5453 (Online) Journal homepage: http://www.tandfonline.com/loi/uopp20
Synthesis and Antimicrobial Activities of Some 3-
Phenanthryl Chalcones
V. Usha, V. Thangaraj & G. Thirunarayanan
To cite this article: V. Usha, V. Thangaraj & G. Thirunarayanan (2018) Synthesis and
Antimicrobial Activities of Some 3-Phenanthryl Chalcones, Organic Preparations and Procedures
International, 50:4, 459-463, DOI: 10.1080/00304948.2018.1468990
To link to this article: https://doi.org/10.1080/00304948.2018.1468990
Published online: 19 Oct 2018.
Submit your article to this journal
Article views: 3
View Crossmark data
Full Terms & Conditions of access and use can be found at
http://www.tandfonline.com/action/journalInformation?journalCode=uopp20

Organic Preparations and Procedures International, 50:459–463, 2018
# 2018 Taylor & Francis Group, LLC
ISSN: 0030-4948 print / 1945-5453 online
DOI: 10.1080/00304948.2018.1468990
OPPI BRIEF
Synthesis and Antimicrobial Activities of Some
3-Phenanthryl Chalcones
V. Usha,1 V. Thangaraj,2 and G. Thirunarayanan3
1Department of Chemistry, University College of Engineering Panruti,
Panruti-607 106, India
2Department of Chemistry, Anna University BIT Campus, Tiruchirappalli-620
024, India
3Department of Chemistry, Annamalai University, Annamalainagar-608
002, India
Chalcones are structurally interesting compounds with important biological activities.
Because of their significance, numerous methods have been reported for the synthesis
of these compounds. For example, recent work has shown the usefulness of potassium
carbonate catalysis under microwave irradiation for synthesis of chalcones.1 Chalcones
have been reported to have antimicrobial,2–4 anti-inflammatory,5 antimalarial,6,7 anti-
leishmanial,8 antioxidant,9 and antitubercular activities.10,11
We now report our results on the preparation and biological activities of some
novel 3-phenanthryl chalcones (Scheme 1). Our synthesis method uses microwave
irradiation and FeCl3-bentonite catalyst and is noteworthy for its convenience, short
reaction times and high yields.
Our synthetic results are shown in Tables 1 and 2. Yields were uniformly 90% or
higher, and the spectroscopic data were consistent with the expected structures.
The measured antibacterial activities of all styryl 3-phenanthryl ketones are pre-
sented in Table 3. All of the compounds displayed activities comparable to or slightly
better than the standard ampicillin.
The observed antifungal activities of all styryl 3-phenanthryl ketones are presented
in Table 4. All of the compounds showed activities comparable to or slightly better
than the standard miconazole in the organisms tested.
In conclusion, we have demonstrated that novel 3-phenanthryl chalcones may be pre-
pared by a convenient method in high yields using FeCl3-bentonite catalyst under micro-
wave irradiation. The synthesized compounds have useful antimicrobial activities. It is
hoped that the ease of preparation will stimulate further research on these materials.
Received August 25, 2017; accepted February 5, 2018.
Address correspondence to V. Usha, Department of Chemistry, University College of
Engineering Panruti, Panruti-607 106, India. E-mail: vushachem2004@gmail.com
459

460
Usha et al.
X= H, 3-Br, 4-Br, 2-Cl, 3-Cl, 4-F, 4-OCH3, 3-CH3, 2-NO2, 4-NO2
Scheme 1. Synthesis of 3-phenanthryl chalcones.
Experimental Section
All chemicals were procured from Sigma Aldrich. The melting points of all the chal-
cones were determined in open glass capillaries on a Mettler FP51 melting point appar-
atus and are uncorrected. Elemental analyses of all ketones were performed on a
Perkin Elmer 240c analyzer. The IR spectra of all compounds were recorded using
KBr discs on an Avatar-300 ThermoNikolet Fourier Transform infrared spectropho-
tometer with the frequency range of 4000–400 cm21. The NMR spectra of com-
pounds were recorded on an INSTRUM AV300 spectrometer, operating at 500 MHz
for 1H spectra and 125.46 MHz for 13C spectra in DMSO solvent using TMS as
internal standard. Mass spectra of all compounds were recorded on a SHIMADZU
GC-MS2010 spectrometer and VARIAN-SATURN 2200 GC-MS spectrometer using
electron impact techniques. The FeCl3-bentonite catalyst was prepared and its purity
examined by a literature method.13 3-Acetylphenanthrene (2 mmol), substituted ben-
zaldehyde (2 mmol), and FeCl3-bentonite (0.3 g, 1.25 mmol) were taken in an acci-
dental explosion proof pressure tube and flushed with argon and tightly capped. The
reaction mixture was shielded and subjected to microwave irradiation for 4-
5 minutes at 650W energy, applying 250V, 5 Amps AC in a microwave oven (LG
Grill, Intellowave Microwave Oven, 160-800W) (Scheme 1) and then cooled to
room temperature. The organic layer was extracted into dichloromethane which, on
filtration and evaporation, gave the solid product. The insoluble catalyst was
recycled by washing the solid remaining on the filter with ethyl acetate (8 mL), then
drying in an oven at 100 ꢀC for 1h. The crude chalcones were recrystallized from
ethanol to obtain pale yellow glittering solids. The synthesized chalcones were fully
characterized by their physical constants, elemental analysis and spectroscopic data,
which are presented in Tables 1 and 2.
Antibacterial Sensitivity Assay
Antibacterial sensitivity assays were performed using the Kirby-Bauer14 disc diffusion
technique. In each Petri plate about 0.5 ml of the test bacterial sample (10 mg of the
bacterial sample dissolved in 100 ml of sterile distilled water) was spread uniformly

3-Phenanthryl Chalcones
461
Table 1
Preparation of 3-Phenanthryl Chalcones
Microanalysis
Time Yield
MW (m) (%)
m.p.
(ꢀ C)
Mass
(m/z)
(%)
Compound
X
MF
C
H
N
(calcd) (calcd) (calcd)
1
2
H
C
23H16
O
308
4
96
91
93
90
90
90
95
95
91
94
106–107
89.59 5.18
—
—
308[Mþ]
386[Mþ],
(108–110)12 (89.58) (5.23)
3-Br
4-Br
2-Cl
3-Cl
4-F
C23H15BrO 386 4.5
C23H15BrO 386 4.5
123–124
117–118
132–133
119–120
132–133
106–107
71.36 3.86
(71.33) (3.90)
71.29 3.88
(71.33) (3.90)
80.59 4.38
(80.58) (4.41)
80.61 4.39
(80.58) (4.41)
84.68 4.59
(84.64) (4.63)
85.15 5.33
338[M2þ
386[Mþ],
]
3
—
338[M2þ
342[Mþ],
]
4
C
23H15ClO 342
C23H15ClO 342
25H15FO 326
4
4
5
4
4
6
6
—
344[M2þ
342[Mþ],
]
5
—
344[M2þ
326[Mþ],
]
6
C
—
328[M2þ
338[Mþ]
]
7
4-OCH3 C24H18O2 338
3-CH3 C24H18 322
—
(108–110)12 (85.18) (5.36)
116–117 89.45 5.59
(115–118)12 (89.41) (5.63)
8
O
—
322[Mþ]
353[Mþ]
353[Mþ]
9
2-NO2 C23H15NO3 353
4-NO2 C23H15NO3 353
122–123
78.19 4.24
(78.17) (4.28) (3.96)
78.22 4.26 3.89
3.92
10
117–118
(115–118)12 (78.17) (4.28) (3.96)
Table 2
The Infrared Carbonyl Stretches (ꢀ, cm21), NMR Chemical Shifts (d, ppm) of Ha, Hb,
Protons, CO, Ca and Cb Carbons of Synthesized 3-Phenanthryl Chalcones
1HNMR
(d, ppm)
IR (m, cm21
COs-cis COs-trans
)
13C NMR (d, ppm)
CO Ca Cb
Compound
X
Ha Hb
1
2
3
4
5
6
7
8
9
H
3-Br
4-Br
2-Cl
3-Cl
4-F
4-OCH3
3-CH3
2-NO2
4-NO2
1651
1633
1631
1639
1643
1683
1685
1629
1691
1687
1604
1600
1602
1600
1587
1597
1594
1600
1610
1608
7.486 7.671 197.35 125.25 138.53
7.492 7.645 197.10 124.83 133.40
7.505 7.637 197.11 125.66 133.39
7.466 7.591 197.10 125.65 138.32
7.447 7.637 196.03 125.66 134.73
7.490 7.668 197.06 126.30 138.22
7.487 7.654 197.01 127.28 138.23
7.434 7.705 197.45 124.35 138.67
7.525 7.774 196.66 124.66 137.93
7.551 7.787 196.67 124.55 136.26
10

462
Usha et al.
Table 3
The Zone of Inhibition (mm) Values of Antibacterial Activity of Substituted Styryl 3-
Phenanthryl Chalcones
Zone of Inhibition (mm)
Compound
X
Gram
Gram positive Bacteria
negative Bacteria
B. subtilis M. luteus S. aureus E. coli P. aeruginosa
1
2
3
4
5
6
7
8
H
7
9
9
10
11
8
7
8
8
7
10
11
10
11
9
8
9
8
8
11
9
11
10
7
10
8
9
7
9
9
7
3-Br
4-Br
2-Cl
3-Cl
4-F
2-OCH3
3-CH3
2-NO2
11
12
12
10
8
11
13
12
10
9
9
9
10
9
9
10
Standard
Control
4-NO2
Ampicillin
DMSO
7
12
–
7
13
–
7
12
–
9
13
–
10
15
–
Table 4
Zone of Inhibition (mm) Values of Antifungal Activity of
Substituted 3-Phenanthryl Chalcones
Zone of Inhibition (mm)
Compound
X
A. niger P. scup T. viride
1
2
3
4
5
6
7
8
H
7
6
8
8
6
8
7
9
8
7
7
8
7
7
10
9
10
10
10
10
9
11
10
9
3-Br
4-Br
2-Cl
3-Cl
4-F
2-OCH3
3-CH3
9
10
Standard
Control
2-NO2
4-NO2
Miconazole
DMSO
9
8
10
–
10
9
10
–
10
11
10
–
over the solidified Mueller Hinton agar using a sterile glass spreader. Then 5 mm diam-
eter discs of Whatman No.1 filter paper, impregnated with the solution of the com-
pound (250 mg/ml of each dissolved in 1 ml of DMSO solvent), were placed on the
medium using sterile foreceps. The plates were incubated for 24 hours at 37ꢀC. After

3-Phenanthryl Chalcones
463
24 hrs, the plates were visually examined and the diameter values of the zones of inhib-
ition were measured. Triplicate results were recorded by repeating the same procedure.
Controls showed luxuriant growth.
Antifungal Sensitivity Assay
Antifungal sensitivity assays were performed using the Kirby-Bauer14 disc diffusion tech-
nique. Potato dextrose agar medium was prepared and sterilized. It was poured into the
plates already containing 1 mL of the fungal species (10 mg of the fungal sample dissolved
in 100 ml of sterile distilled water). Whatman No.1 5 mm discs were impregnated with the
test solution, prepared by dissolving 15 mg of the enone in 1 mL of DMSO solvent. The
medium was allowed to solidify and kept for 24 hrs. Then the plates were visually exam-
ined and the diameter values of the zones of inhibition were measured. Triplicate results
were recorded by repeating the same procedure. Controls showed luxuriant growth.
References
1. Y. K. Srivastava, Rasayan J. Chem., 1, 884 (2008).
2. Y. Rajendra Prasad, A. Lakshmana Rao and R. Rambabu, E-J. Chem., 5, 461 (2008).
ꢀ
ꢀ
3. S. N. Lopez, M. V. Castelli, S. A. Zacchino, J. N. Domınguez, G. Lobo, J. C. Charris,
ꢀ
ꢀ
J. C. G. Cortes, J. C. Ribas, C. Devia, A. M. Rodrıguez and R. D. Enriz, Bioorg. Med.
Chem., 9, 1999 (2001).
4. B. Baviskar, S. Patel, B. Baviskar, S. S. Khadabadi and M. Shiradkar, Asian J. Res. Chem.,
1, 67 (2008).
ꢀ
5. F. Herencia, M. L. Ferrandiz, A. Ubeda, J. N. Domınguez, J. E. Charris, G. M. Lobo and
M. J. Alcaraz, Bioorg. Med. Chem. Lett., 8, 1169 (1998).
6. X. Wu, P. Wilairat and M. L. Go, Bioorg. Med. Chem. Lett., 12, 2299 (2002).
7. A. Agarwal, K. Srivastava, S. K. Puri and P. M. S. Chauhan, Bioorg. Med. Chem., 13, 6226 (2005).
8. T. Narender, T. Khaliq, Shweta, Nishi, N. Goyal and S. Gupta, Bioorg. Med. Chem., 13,
6543 (2005).
9. J. H. Cheng, C. F. Hung, S. C. Yang, J. P. Wang, S. J. Won and C. N. Lin, Bioorg. Med.
Chem., 16, 7270 (2008).
10. Y. M. Lin, Y. Zhou, M. T. Flavin, L. M. Zhou, W. Nie, F. C. Chen, Bioorg. Med. Chem.,
10, 2795 (2002).
11. P. M. Sivakumar, S. P. Seenivasan, V. Kumar and M. Doble, Bioorg. Med. Chem. Lett., 17,
1695 (2007).
12. S. S. Misra, R.S. Tiwari, B. Nath, Indian J. Appl. Chem., 34, 260 (1971).
13. I. Muthuvel, S. Dineshkumar, K. Thirumurthy, R. Rajasri and G. Thirunarayanan, Indian J.
Chem., 55B, 252 (2016).
14. A. W. Bauer, W. M. M. Kirby, J. C. Sherris and M. Truck, Am. J. Clin. Pathol., 45, 493
(1966).