WSN 52 (2016) 14-30 EISSN 2392-2192
Synthesis and antimicrobial activity of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-
one compounds
S. Balaji1, R. Senbagam1, M. Rajarajan1, R. Vijayakumar1, V. Manikandan1, G. Vanangamudi1, G. Thirunarayanan2,*
1PG & Research Department of Chemistry, Government Arts College, C. Mutlur, Chidambaram - 608 102, India
2Department of Chemistry, Annamalai University, Annamalainagar - 608 002, India
*E-mail address: [email protected] , [email protected]
ABSTRACT
In an effort to develop antimicrobial agents, a series of substituted (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-one compounds were synthesized by crossed-aldol condensation reaction of 4-fluoro-3-methyl acetophenone with various substituted benzaldehydes in the presence of sodium hydroxide. The synthesized compounds were characterized by means of their UV, IR and NMR spectral data. The synthesized substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en- 1-one compounds were tested for their antibacterial and antifungal activities by the Bauer-Kirby disc diffusion method.
Keywords: Antibacterial activity; Antifungal activity; Bacillus subtilis; vibrio cholera
1. INTRODUCTION
Survival of the fittest is the basis for life and for the human beings also. The biggest threats for human beings are the various diseases, scientists and doctors are still fighting to find solutions with various forms of medications. Today’s developed medicines are results of
relentless effort made by human civilization time to time. When the period of synthetic drugs began, it opened thousand doors for the development of various synthetic molecules with potential action. Chalcones (prop-2-en-1-ones) either natural or synthetic are known to exhibit various biological activities. The name chalcones (prop-2-en-1-ones) was coined by Tambor and Kostanecki [1]. The chalcones, two aromatic rings are linked by an aliphatic three carbon chain which bears a very good synthon (starting reagent) so that variety of novel heterocyclics with good pharmaceutical profile can be designed.
The 1,3-diphenyl prop-2-en-1-one are a class of compounds exhibit diverse pharmacological activities, such as antimalarial [2], anti-inflammatory [3], antileishmanial [4], antioxidant [5-8], antitumor [9], antibacterial [10], anti-inflammatory [11], anti-parasitary [12], anticonvulsant [13], antimicrobial [14], antinociceptives [15] associated with diseases such as Alzheimer, Huntington and inflammatory arthritis [16].
A practical method for the synthesis of such compounds is of great interest in synthetic organic chemistry. These 1, 3-diphenyl prop-2-en-1-ones are prepared by condensing aryl ketones with aromatic aldehydes in presence of suitable condensing agents. Depending on the substitution of the two aromatic rings, the chalcones can exhibit different biological activity.
Literature survey shows that there is no information available regarding antimicrobial activity of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one compounds.
Therefore the authors have taken efforts to synthesis these substituted (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-one compounds from 4-fluoro-3-methyl acetophenone with various substituted benzaldehydes by crossed-aldol condensation reaction.
The synthesized substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one compounds have been confirmed by their physical constants, UV, IR and NMR spectral data.
The antimicrobial activity of all the synthesized substituted (E)-1-(4-fluoro-3-methylphenyl)- 3-phenylprop-2-en-1-one compounds have been studied using by Kirby-Bauer method [17].
2. EXPERIMENTAL 2. 1. Material and Methods
All the chemicals used in this investigation were purchased from Sigma-Aldrich, E- Merck and Himedia chemical companies. Melting points of all synthesized substituted (E)-1- (4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one were determined in open glass capillaries on Mettler FP51 melting point apparatus and were uncorrected. The Shimadzu- 1650 ultraviolet spectrophotometer was utilized for recording the absorption maxima (λmax, nm), of all substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-ones in spectral grade methanol. Infrared spectra (KBr, 4000-400 cm-1) of all substituted (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-ones were recorded in Avatar-300 Fourier transform spectrophotometer. The NMR spectra of all compounds were recorded in Bruker AV400 NMR spectrometer, operating 400 MHz and 500 MHz for 1H and 100 MHz for 13C spectra in CDCl3 solvent using TMS as internal standard.
2. 2. General procedure for synthesis of (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop- 2-en-1-one compounds
A mixture of 4-fluoro-3-methyl acetophenone (0.05 mol) and various substituted benzaldehydes (0.05 mol) were dissolved in 50 ml absolute ethanol in a 250 ml round-bottom
flask equipped with a magnetic stirrer. Then 50 ml NaOH solution (1 g in 50 ml H2O) was added drop wise to the reaction mixture on vigorous stirring for 30 minutes when solution became turbid. The reaction mixture was neutralized by 0.1 N HCl by the precipitation occurred [18,19]. On filtering off, the crude substituted (E)-1-(4-fluoro-3-methylphenyl)-3- phenylprop-2-en-1-one was dried in air and recrystallized using ethanol to get glittering color solid, and their melting points were observed. The general reaction is shown in Scheme 1.
Scheme 1. Synthesis of (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-ones.
The physical constants and analytical data of synthesized (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-ones are presented in Table-1.
Table 1. Physical constants of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop- 2-en-1-one compounds.
Entry X M. F. M. W. Yield
(%)
m.p.
(°C)
1 H C16H13FO 240.27 86 58-60
2 3-Br C16H12FBrO 319.17 81 57-59 3 4-Br C16H12FBrO 319.17 90 91-93 4 2-Cl C16H12FClO 274.72 83 60-62 5 3-Cl C16H12FClO 274.72 92 61-63 6 4-Cl C16H12FClO 274.72 93 99-101 7 3-F C16H12F2O 258.26 82 80-82 8 4-F C16H12F2O 258.26 94 88-91 9 4-OCH3 C17H15FO2 270.30 91 49-51 10 4-CH3 C17H15FO 254.30 82 97-99 11 3-NO2 C16H12FNO3 285.27 85 121-123
The UV, IR and NMR spectral data[20] of these substituted (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-one are presented in given below
(E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one (1):
UV λmax; = 309; IR (KBr): v = 1662.64 cm-1 (CO s-cis), 1597.06 cm-1 (CO s-trans); 1244.09 cm-1 (CHip)761.88 (CHop); 1051.20 cm-1 (CH=CHop); 557 cm-1 (C=Cop) 2922.52 cm-1 (CH aromatic.); 1499 cm-1 (C=C str); 3051 cm-1 (CH str CH3.); 754.95, 696.73cm-1 (mono substituted).; 850.32 cm-1(meta F) 1H NMR (CDC13): (ppm) = 7.52 (d; J = 15.6 Hz, 1H,
=CH),7.822 (d; J = 16 Hz, 1H, =CH), 2.369 (s; 3H, CH3.), 13C NMR (CDCl3) (ppm)=
121.71(Cα); 144.78(Cβ); 189.02(CO); 14.5(CH3); 167.3(C-F).
(E)-3-(3-bromophenyl)-1-(4-fluoro-3-methylphenyl) prop-2-en-1-one (2):
UV λmax; = 301.5; IR (KBr): v = 1658.78 (CO s-cis), 1600.92 cm-1 (CO s-trans); 1240.23 cm-1 (CHip), 783.10 cm-1 (CHop); 1060.85 cm-1 (CH=CHop); 538.14 cm-1 (C=Cop) 2920.23 cm- 1 (CH aromatic.); 1492.90 cm-1 (C=C str); 3018 cm-1 (CH str CH3.); 783.10, 704.02 cm-1 (mono substituted); 856.39 cm-1(meta F) 1H NMR (CDC13): (ppm) = 7.490 (d; J = 16.4 Hz, 1H,
=CH), 7.705 (d; J = 15.6 Hz, 1H, =CH), 2.306 (s; 3H, CH3.), 13C NMR(CDCl3)(ppm) = 122.89(Cα); 142.83(Cβ); 188.47(CO); 14.55(CH3); 165.629(C-F); 123.09(C-Br).
(E)-3-(4-bromophenyl)-1-(4-fluoro-3-methylphenyl) prop-2-en-1-one (3)
UV λmax; = 315.0; IR (KBr): v = 1662.64(CO s-cis), 1595.13 cm-1 (CO s-trans); 1242.16 cm-1 (CHip), 812.03 cm-1 (CHop); 1047.35 cm-1 (CH=CHop); 530.42 cm-1 (C=Cop) 2922.16 cm-1 (CH aromatic.); 1498.69 cm-1 (C=C str); 3115.04 cm-1 (CH str CH3.); 738.74, 682.80cm-1 (mono substituted); 867.97 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.508 (d; J= 16.4 Hz, 1H,
=CH), 7.747 (d; J = 15.6 Hz, 1H, =CH), 2.338 (s; 3H, CH3.), 13C NMR(CDCl3): (ppm)=
122.15(Cα); 143.32(Cβ); 188.73(CO); 14.549(CH3); 165.602(C-F); 124.848(C-Br).
(E)-3-(2-chlorophenyl)-1-(4-fluoro-3-methylphenyl) prop-2-en-1-one (4):
UV λmax; = 302.5; IR (KBr): v = 1664.57 (CO s-cis), 1593.20 cm-1 (CO s-trans); 1244.09 cm-1 (CHip), 817.82 cm-1 (CHop); 1043.49 cm-1 (CH=CHop); 551.64 cm-1 (C=Cop) 2922.16cm-1 (CH aromatic.); 1496.76 cm-1 (C=C str); 3059.10 cm-1 (CH str CH3.); 752.24, 680.87cm-1 (mono substituted); 866.04 cm-1 (meta F) 1H N M R (CDC13): (ppm) = 7.467 (d; J = 15 Hz, 1H,
=CH), 8.182 (d; J = 16 Hz, 1H, =CH), 2.318 (s; 3H, CH3.), 13C NMR (CDC13): (ppm)
=124.59(Cα); 140.60(Cβ); 189.03(CO); 14.50(CH3); 165.34(C-F); 134.01(C-Cl).
(E)-3-(3-chlorophenyl)-1-(4-fluoro-3-methylphenyl) prop-2-en-1-one (5)
UV λmax; = 306.0; IR (KBr): v = 1660.50 (CO s-cis), 1597.06 cm-1 (CO s-trans); 1244.09 cm-1 (CHip), 792.74 cm-1 (CHop); 1051.20 cm-1 (CH=CHop); 567.07 cm-1 (C=Cop) 2920.23-1 (CH aromatic.); 1490.97 cm-1 (C=C str); 3080.32 cm-1 (CH str CH3.); 750.31, 661.85cm-1 (mono substituted); 844.82 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.505 (d; J = 15.6 Hz, 1H,
=CH), 7.772 (d; J = 16.4 Hz, 1H, =CH), 2.368 (s; 3H, CH3.), 13C NMR(CDC13)(ppm)=
122.85(Cα); 149.97(Cβ); 188.53(CO); 14.53(CH3); 165.64(C-F); 133.98(C-Cl).
(E)-3-(4-chlorophenyl)-1-(4-fluoro-3-methylphenyl) prop-2-en-1-one (6)
UV λmax; = 312.5; IR (KBr): v = 1664.57 (CO s-cis), 1597.06 cm-1 (CO s-trans); 1244.09 cm-1 (CHip), 819.75cm-1 (CHop); 1407.35 cm-1 (CH=CHop); 553.57 cm-1 (C=Cop) 2920.23cm-1 (CH aromatic.); 1490.97 cm-1 (c=c str); 3053.32 cm-1 (CH str CH3.); 746.45, 669.30cm-1 (mono
substituted); 818.75 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.485 (d; J = 15.5 Hz, 1H,
=CH), 7.750 (d; J = 15.5 Hz, 1H, =CH), 2.340 (s; 3H, CH3.), 13C NMR (CDC13)(ppm) = 122.06(Cα); 143.25(Cβ); 188.69(CO);14.55(CH3);165.45(C-F); 134.05(C-Cl).
(E)-1-(4-fluoro-3-methylphenyl)-3-(3-fluorophenyl) prop-2-en-1-one (7)
UV λmax; = 303.5; IR (KBr): v = 1660.71 (CO s-cis), 1591.27 cm-1 (CO s-trans); 1242.16 cm-1 (CHip), 815.89cm-1 (CHop); 1049.28 cm-1 (CH=CHop); 551.64 cm-1 (C=Cop) 2920.37cm-1 (CH aromatic.); 1490.97 cm-1 (C=C str); 3080.32 cm-1 (CH str CH3.); 750.31, 661.58cm-1 (mono substituted); 815.89 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.497 (d; J = 15.6 Hz, 1H,
=CH), 7.749 (d; J = 15.6 Hz, 1H, =CH), 2.357 (s; 3H, CH3.), 13C NMR (CDC13)(ppm)=
122.84(Cα); 143.18(Cβ); 188.61(CO);14.54(CH3);165.62(C-F); 161.82(C-F).
(E)-1-(4-fluoro-3-methylphenyl)-3-(4-fluorophenyl) prop-2-en-1-one (8)
UV λmax; = 310.5; IR (KBr): v = 1664.57 (CO s-cis), 1595.31 cm-1 (CO s-trans); 1236.37 cm-1 (CHip), 863.60 cm-1 (CHop); 1049.28 cm-1 (CH=CHop); 595.14 cm-1 (C=Cop) 2924.09 cm-1 (CH aromatic.); 1502.55 cm-1 (C=C str); 3064.89 cm-1 (CH str CH3.); 748.38, 682.80cm-1 (mono substituted); 823.60 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.447 (d; J = 15.5 Hz, 1H,
=CH), 7.782 (d; J = 15.5 Hz, 1H, =CH), 2.369 (s; 3H, CH3.), 13C NMR (CDC13): (ppm) = 121.45(Cα); 143.43(Cβ); 188.80(CO); 14.56(CH3); 165.29(C-F); 163.09(C-F).
(E)-1-(4-fluoro-3-methylphenyl)-3-(4-methoxyphenyl) prop-2-en-1-one (9)
UV λmax; = 326.0; IR (KBr): v = 1664.57 (CO s-cis), 1597.06 cm-1 (CO s-trans); 1247.94 cm-1 (CHip), 825.53 cm-1 (CHop); 1043.49 cm-1 (CH=CHop); 551.64 cm-1 (C=Cop) 2912.51 cm-1 (CH aromatic.); 1504.48 cm-1, (C=C str); 3053.32 cm-1 (CH str CH3.); 748.38, 684.73cm-1 (mono substituted).; 825.53 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.370 (d; J = 15.6 Hz, 1H,
=CH), 7.763 (d; J = 15.6 Hz, 1H, =CH), 2.383 (s; 3H, CH3.), 3.735 (s; 3H, OCH3.) 13CNMR (CDC13) :(ppm) = 119.34(Cα); 144.63(Cβ); 189.04(CO); 14.563(CH3); 165.36(C-F);
161.715(C-OCH3); 5.391(OCH3).
(E)-1-(4-fluoro-3-methylphenyl)-3-(p-tolyl) prop-2-en-1-one (10)
UV λmax; = 324.0; IR (KBr): v = 1658.78 (CO s-cis), 1597.06 cm-1 (CO s-trans); 1238.30 cm-1 (CHip), 813.96 cm-1 (CHop); 1045.42 cm-1 (CH=CHop); 555.50 cm-1 (C=Cop) 2924.09 cm-1 (CH aromatic.); 1496.76 cm-1 (C=C str); 3053.26 cm-1 (CH str CH3.); 738.14,682.80 cm-1 (mono substituted); 813.96 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.481 (d; J = 15.5 Hz, 1H,
=CH), 7.807 (d; J = 15.5 Hz, 1H, =CH), 2.416 (s; 3H, CH3.), 1.33 (s; 3H, CH3.), 13C NMR (CDC13): (ppm)=120.74(Cα);144.91(Cβ);189.19(CO);14.59(CH3);165.20(C-F), 21.54(CH3).
(E)-1-(4-fluoro-3-methylphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (11)
UV λmax; = 301.0; IR (KBr): v = 1666.50 (CO s-cis), 1598.99cm-1 (CO s-trans); 1246.02 cm-1 (CHip), 810.10 cm-1 (CHop); 1047.35 cm-1 (CH=CHop); 542.00 cm-1 (C=Cop) 2918.03 cm-1 (CH aromatic.); 1523.76 cm-1 (C=C str); 3084.18 cm-1 (CH str CH3.); 748.38, 671.23 cm-1 (mono substituted).; 810.10 cm-1 (meta F) 1H NMR (CDC13): (ppm) = 7.117 (d; J = 16.4 Hz, 1H,
=CH), 7.847 (d; J = 16 Hz, 1H, =CH), 2.375 (s; 3H, CH3.), 13C NMR (CDC13): (ppm) = 122.27(Cα); 141.60(Cβ); 188.18(CO); 14.118(CH3); 165.819(C-F); 148.75(C-NO2).
3. RESULTS AND DISCUSSION 3. 1. Spectra
The synthesized chalcones were characterized by their Uv-visible, IR and NMR spectra.
The parent chalcones of this present study was illustrated as follows.
3. 1. 1. UV-Visible spectra
The UV–visible spectra of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2- en-1-one compound shown in (Fig. 1). The UV–visible spectra below 340 nm, a single peak is observed for the of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one of (chalcones) transition band due to π-π* at 309.00 λmax (nm). According to the valence band theory, as the conjugation increases, the energy difference between the highest occupied and the lowest unoccupied π-orbitals decreases and hence the wave length of the absorption band increases.
Fig. 1. The UV spectrum of (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one
3. 1. 2. IR spectrum
The IR frequencies of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en- 1-one shown in (Fig. 2)
Fig. 2. The IR spectrum of (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one
3. 1. 3. 1H NMR spectrum
The complete assignment of the IH NMR spectra is given here (Fig. 3). The spectrum was recorded at 400 and 500 MHz The assignment is done on the basis of chemical shifts, multiplicities and coupling constants. The 1H NMR spectrum (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-one in CDCl3 solvent.
Fig. 3. 1H NMR spectrum of (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one
3. 1. 4. 13C NMR spectrum
The complete assignment of the 13C NMR spectra is given here (fig.4). The spectrum was recorded at 100 MHz. The assignment is done on the basis of chemical shifts, multiplicities peeks and coupling constants. The 13C NMR spectrum of (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-one in CDCl3 solvent was shown in (Fig. 4).
Fig. 4. The 13C NMR spectrum (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one
3. 2. Antimicrobial activity
3. 2. 1. Antibacterial sensitivity assay
The antibacterial activities of all synthesized substituted (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-one compounds have been studied against five gram positive pathogenic strains Bacillus subtilis, Clostridium botulini, Staphylococcus aureus, Nocardia species and Enterococcus species and five gram negative strains Escherichia coli, klebsiella pneumonia, proteus mirabilis, salmonella typhi and vibrio cholera have been studied by Kirby-Bauer method. Ciprofloxacin was used as standard. The antibacterial screening effect of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one compounds is shown in (Fig. 5) (Plates 1-20).
The measured zone of inhibition values are given in Table 2 and the corresponding clustered column chart is shown in (Fig. 6). The zone of inhibition (mm) values of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one compounds reveals that most of the compounds have shown moderate, good and excellent (some of the poor) activity against all the ten microorganisms evaluated in the present investigation. The 4-CH3 substituted compound has shown excellent activity against B. subtilis, Enterococcus species, Nocardia species, Staphylococcus aureus,and vibrio cholera.
The 3-Br substituted compound has shown excellent activity against Enterococcus species, Nocardia species, Escherichia coli and proteus mirabilis. The 3-F substituted compound has shown excellent activity against Bacillus subtilis, Enterococcus species, Nocardia species, and Escherichia coli. The 4-OCH3 substituted compound has shown excellent activity against Bacillus subtilis, Nocardia specie and proteus mirabilis. The H (parent) substituted compound has shown excellent activity against Staphylococcus aureu and Escherichia coli. The 4-Br substituted compound has shown excellent activity against klebsiella pneumonia, and proteus mirabilis.
The 2-Cl substituted compound has shown excellent activity against Clostridium botulini, and Enterococcus species. The 4-F substituted compound has shown excellent activity against Staphylococcus aureus and vibrio cholera. 3-Cl substituted compound has shown excellent activity against salmonella typhi. The 4-Cl substituted compound has shown excellent activity against Nocardia species. The remaining substituted compounds have shown good and moderate antibacterial activity.
Plate 1 Plate 2 Plate 3 Plate 4
Plate 5 Plate 6 Plate 7 Plate 8
Plate 9 Plate 10 Plate 11 Plate 12
Plate 13 Plate 14 Plate 15 Plate 16
Plate 17 Plate 18 Plate 19 Plate 20
Fig. 5. Antibacterial activity of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2- en-1-one compounds (petri plates)
Table 2. Zone of inhibition (mm) values of antibacterial activity of substituted (E)-1-(4- fluoro-3-methylphenyl)-3-phenylprop-2-en-1-one compounds.
S. No. X
Zone of Inhibition (mm)
Gram positive Bacteria Gram negative Bacteria
B.subtilis C.botulini Enterococcus sp Nocardia sp S. aureus E.coli K.pneumonia P.mirabilis s.typhi v.cholerae
1 H 7 9 7 11 17 12 7 10 0 14
2 3-Br 7 8 19 13 7 11 9 12 0 9
3 4-Br 10 11 11 9 0 0 13 14 11 13
4 2-Cl 7 17 14 11 0 8 9 7 12 10
5 3-Cl 9 13 12 0 9 8 10 0 16 14
6 4-Cl 0 10 9 17 10 9 9 9 7 9
7 3-F 12 7 13 20 10 19 8 7 11 0
8 4-F 10 7 9 9 20 10 8 10 9 18
9 4-OCH3 13 7 8 13 10 10 0 12 14 10
10 4-CH3 15 11 16 16 20 10 0 10 10 22
11 3-NO2 10 11 7 9 10 10 0 11 10 0
Standard Ciprofloxacin 10 14 12 12 13 10 12 11 14 14
Control DMSO 0 0 0 0 0 0 0 0 0 0
Fig. 6. Antibacterial activity of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2- en-1-one compounds (clustered column chart).
0 5 10 15 20 25
zone of inhibition
B.subtilis C.botulini Enterococcus sp Nocardia sp s. aureus E.coli K.pneumonia P.mirabilis s.typhi
1. H 2. 3-Br 3. 4-Br 4. 2-Cl 5. 3-Cl 6. 4-Cl 7. 3-F 8. 4.F 9. 4-OCH3
3. 2. 2. Antifungal sensitivity assay
The antifungal activities of all synthesized substituted (E)-1-(4-fluoro-3-methylphenyl)- 3-phenylprop-2-en-1-one compounds have been studied against five fungal species namely A.
niger, A. flavus, C. albicans, T. viride and M. species. The disc diffusion technique has been followed using the Kirby–Bauer method, at a concentration of 250 μg/mL and ciprofloxacin was used as standard.
The antifungal screening effect of prepared substituted (E)-1-(4-fluoro-3- methylphenyl)-3-phenylprop-2-en-1-one compounds is shown in (Fig. 7) (Plates 21–30). The measured zone of inhibition values are given in Table 3 and the corresponding Clustered column chart is shown in (Fig 8).
All the compounds have shown moderate, good and excellent activity against all the five fungal species evaluated in general. The 3-Cl and 4-Cl substituted compounds have shown excellent activity against A. flavus and T. vidide. The H (parent) substituted compound has shown excellent activity against C. albicans. 4-CH3, substituted compound shave shown excellent activity against A. flavus. The 3-NO2 substituted compound has shown excellent activity against A. niger.
Plate 21 Plate 22
Plate 23 Plate 24
Plate 25 Plate 26
Fig. 7. Antifungal activity of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop -2-en-1-one (petri plates)
Table 3. Zone of inhibition (mm) values of antifungal activities of substituted (e)-1-(4-fluoro- 3-methylphenyl)-3-phenylprop-2-en-1-one compounds.
S.NO. X
Zone of Inhibition (mm)
A. niger A. flavus C. albicans M. species T. virite
1 H 0 0 21 13 0
2 3-Br 0 0 13 0 16
3 4-Br 0 0 0 0 7
4 2-Cl 0 0 0 0 7
5 3-Cl 0 15 0 20 9
6 4-Cl 0 15 0 16 0
7 3-F 0 9 0 11 0
8 4-F 0 9 16 10 0
9 4-OCH3 0 10 0 10 9
10 4-CH3 0 13 0 0 10
11 3-NO2 15 7 0 0 13
Standard Ciprofloxacin 12 10 19 15 17
Control DMSO 0 0 0 0 0
Plate 27 Plate 28
Plate 29 Plate 30
Fig. 8. Antifungal activity of substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop- 2- en-1-one (clustered column chart)
4. CONCLUSIONS
We have synthesized a series of substituted (E)-1-(4-fluoro-3-methylphenyl)-3- phenylprop-2-en-1-one and its derivatives by crossed aldol condensation reaction.
Synthesized substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-ones was confirmed by their physical constants, UV, IR and NMR spectral data. The antimicrobial activity of all the substituted (E)-1-(4-fluoro-3-methylphenyl)-3-phenylprop-2-en-1-ones by using five gram positive bacteria, five gram negative bacteria and five fungal strain by using disc- diffusion method. The 4-CH3 substituted compound has shown excellent activity against five bacterial species namely B. subtilis, Enterococcus species, Nocardia species, Staphylococcus aureus and vibrio cholera.. The 3-Br substituted compound has shown excellent activity against four bacterial species namely Enterococcus species, Nocardia species, Escherichia coli and proteus mirabilis., The 3-F substituted compound has shown excellent activity against four bacterial species namely Bacillus subtilis, Enterococcus species, Nocardia species, and Escherichia coli,. The 3-Cl, 4-Cl substituted compounds have shown excellent activity against two fugal species namely A. flavus and T. vidide.
Acknowledgment
The authors thank DST NMR Facility, Department of Chemistry, Annamalai University, Annamalainagar-608 002, for recording NMR spectra of all compounds.
0 5 10 15 20 25
zone of inhibition
A.niger A.flavus C.albicans M.species T.virite 1. H 2. 3-Br 3. 4-Br 4. 2-Cl 5. 3-Cl 6. 4-Cl 7. 3-F 8. 4.F 9. 4-OCH3 10. 4-CH3 11. 3-NO2
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( Received 16 June 2016; accepted 10 July 2016 )
