International Journal of Bioorganic Chemistry
Volume 1, Issue 1, December 2016, Pages: 21-30

Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-ones

P. Christuraj1, P. R. Rajakumar1, C. Geetha1, G. Vanangamudi1, R. Arulkumran1, R. Sundararajan1, G. Thirunarayanan2, *

1Post Graduate and Research Department of Chemistry, Government Arts College, C-Mutlur, Chidambaram, India

2Chemistry Department, Annamalai University, Annamalainagar, India

Email address:

(G. Thirunarayanan)
(G. Thirunarayanan)

*Corresponding author

To cite this article:

P. Christuraj, P. R. Rajakumar, C. Geetha, G. Vanangamudi, R. Arulkumran, R. Sundararajan, G. Thirunarayanan. Synthesis, Characterization and Biological Study of Some (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-Ones. International Journal of Bioorganic Chemistry. Vol. 1, No. 1, 2016, pp. 21-30. doi: 10.11648/j.ijbc.20160101.13

Received: December 9, 2016; Accepted: January 4, 2017; Published: January 24, 2017


Abstract: About eleven substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones have been synthesized by Crossed-Aldol condensation using simple stirring of 5-bromo-2-thiophen aldehyde and various substituted acetophenones at room temperature. The obtained yields of this condensation was more than 89%. They are characterized by their analytical, UV, FT-IR and NMR spectral data. The antimicrobial activities of all synthesized chalcones have been evaluated by Bauer-Kirby disc diffusion method using gram positive and gram negative bacterial and fungal strains. From the mm of zone of inhibition values the anti-bacterial and antifungal activities of all ketones have been discussed.

Keywords: (E)-3-(5-Bromothiophen-2-yl)-1-phenylprop-2-en-1-Ones, IR Spectra, NMR Spectra, Antibacterial and Antifungal Activities


1. Introduction

Chalcones are well known intermediate compounds for synthesizing various pyrazoles such as pyrimidines. The presence of unsaturated keto functional group is responsible for the various activities, such as anti-bacterial and anti-malarial and antifungal activities. Synthetic and naturally occurring aryl chalcones has been mostly studied and recognized as one of the medicinal significant molecules. Various synthetic methods available for synthesizing chalcones such as Aldol, Crossed-Aldol, Claisen-Schmidt, Knovenagal reactions, Greener methods-Grinding of reactants, solvent free and oxides of nanoparticles with microwave heating. Chemists are paying much more interest in the application of solvent free synthetic methods [1]. Also microwave assisted solvent free Aldol and Crossed-Aldol condensation [2-4] was useful for synthesis of carbonyl compounds. Recently, John Joseph et. al., [5] synthesized some 2, 4-dimethoxy phenyl chalcones using fly ash is catalyst for green synthetic methodology. Many catalysts were used for proceedings the above said reactions namely, MgCl2 [6], silica-sulphuric acid [7], anhydrous zinc chloride, ground chemistry catalysts-grinding the reactants with sodium hydroxide [8], aqueous alkali in lower temperature, solid sulphonic acid from bamboo [9], barium hydroxide [10] anhydrous sodium bicarbonate [11], microwave assisted synthesis [12], flyash:water [13], fly-ash: H2SO4 [14], fly-ash: PTS [15], NaOH-CTABr [16], SiO2-H3PO4 [17], SOCl2 [18] and sulfated titania [19]. These chalcones also used as corrosion inhibitors in iron and steel utensil and equipment manufacturing steel industries [20]. These chalcones are also precursor key intermediate for synthesis of important biologically active higher organic heterocycles such as flavones, flavonoids, chromones, aurones, isoxazole, quinlinones, thiodiazine, benzodiazepine and azole related compounds [21,22].

Chalcones from the natural products with distribution in fruits, vegetable, spices, tea and soy based food stuff, have been recently subjects of great interest for their interesting pharmacological activities [23]. Chalcones have many useful activities like anti-inflammatory [24-26], anti-microbial [27,28] anti-fungal [29], Anti-oxidant [30], cytotoxic [30], anti-tumor [31] and anti-cancer activities [32,33] in their own. Most of chalcone derivatives are inhibit several important enzymes in cellular systems, including aldose reductase epoxide hydrdose [34], xanthine oxidate [35], rotein tyrosine linase [36] and guinosa reductase [37]. For developing organic synthesis of the non-conventional technique get the popularity, because the microwave induced enrichment of organic reaction. This technique is easy to access higher yields, elevated temperature, ultimate control and rapid synthesis of organic compounds. Within the above view there is no report available in the literature for the synthesis of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones and the study of their antimicrobial activities. Hence, the authors have taken efforts to synthesis the titled compounds for evaluating the antimicrobial activities.

2. Experimental

2.1. Methods and Materials

All chemicals procured from Aldrich chemical company Bangalore. Uncorrected Suntex melting point apparatus are detect the melting points of all aryl chalcones used by the open glass capillaries. The UV spectra of the chalcones synthesized have been noted using double beam ELICO- BL222 Bio-Spectrophotometer. Infrared spectra (KBr, 4000-400cm-1) have been recorded on FT-IR AVATAR-300 spectrophotometer. BRUKER-500MHz Nuclear Magnetic Resonance spectrometers have been used for noted proton and 13C spectra in CDCl3 solvent using internal standard is TMS. The micro analyses of these aryl chalcone compounds were performed in Thermofinnigan analyzer

2.2. General Procedure for Synthesis of (E)-3-(5-Bromothiophen-2-yl)-1- phenylprop -2-en-1-ones

An appropriate mixture of 5-bromothiophene-2-carbaldehyde (100 mmol) and ortho, meta and para substituted acetophenones (100mmol) and aqueous sodium hydroxide (200 ml 0.5M) in presence of absolute ethyl alcohol (Figure 1) are taken in the conical flask. The above reactants are vigorously stirred for 30 minutes at room temperature [38]. After complete conversion of the aldehydes as examined by TLC method, the mixture was permitted to stand 20 minutes. The obtained solid was separated by simple filtration. The crude product was recrystallized using absolute ethyl alcohol and the products are well dried and keep in a desiccator.

Figure 1. Synthesis of (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones.

2.3. Antimicrobial Activities

All the (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one compounds possess a wide range of microbial activities these multi-prolonged activities are associated with different substituents and the unsaturation of C=C moiety in between the aryl rings. Hence, it is intended to study their anti-microbial activities against their respective microbes-bacterial and fungal strains.

Table 1. The physical constants, yield and analytical data of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones.

Table 2. The ultraviolet absorption maxima (λmax, nm), and infrared absoptions (ʋ, cm-1) spectral values of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones.

Entry X UV (λmax, nm) IR n(cm-1)
COs-cis COs-trans CHip CHop CH=CHop C=Cop
1 H 265 1658 1587 1197 781 1039 522
2 3-Br 328 1654 1577 1199 790 1041 530
3 4-Br 322 1654 1589 1111 794 1068 524
4 3-Cl 323 1653 1583 1199 798 1016 538
5 4-Cl 322 1656 1591 1176 790 1016 532
6 4-F 348 1666 1595 1163 798 1045 576
7 3-OCH3 333 1658 1579 1193 719 1022 582
8 4-OCH3 313 1656 1597 1166 790 1020 596
9 4-CH3 316 1658 1577 1188 790 1024 567
10 3-NO2 310 1656 1597 1166 790 1020 582
11 4-NO2 315 1654 1581 1107 798 1028 555

Table 3. The NMR spectral chemical shifts (d, ppm) of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones.

Entry X 1H NMR 13C NMR
CO
1 H 7.220 7.804 188.68 128.11 136.62
2 3-Br 7.141 7.816 188.05 126.88 132.82
3 4-Br 7.162 7.820 188.41 128.11 136.79
4 3-Cl 7.152 7.824 188.16 126.45 137.01
5 4-Cl 7.171 7.817 188.20 120.32 132.69
6 4-F 7.085 7.817 187.80 120.38 134.22
7 3-OCH3 7.200 7.806 189.19 119.45 136.23
8 4-OCH3 7.240 7.800 187.76 115.15 135.50
9 4-CH3 7.220 7.793 188.94 120.99 132.17
10 3-NO2 7.241 7.895 187.11 127.17 133.98
11 4-NO2 7.165 7.860 187.97       123.92 137.99

2.3.1. Measurement of Antibacterial Sensitivity Assay

Kirby Bauer disc diffusion method [39]used to study the anti-bacterial sensitivity. Using sterile glass spreader the test bacterial sample (0.5 cm3) is spread uniformly over the solidified Mueller Hinton [40] agar for each Petri plate. The sterile forceps are used to impregnating the Whatmann No.1 filter paper with the solution of the compound in 5mm diameter discs.

To prevent the collection of water droplets over the medium to keep the plates are incubated for 24 hours at 37°C temperature. The plates are visually examined after 24 hours the inhibition zone values of diameter are measured. The above procedure is followed to evaluate by triplicate results.

The antibacterial sensitivity of all the synthesized aryl chalcones have been analysed against four gram positive pathogenic strains S. Aureus [41], S. Pyogenes [42], M. Luteus [43,44], B. Substilis [45,46] and six gram negative strains K. Pneumoniae [47], V. Cholerae [48], K. Oxytoca [49], P. Mirabilis [50], E. Coli [44,51], P. Aeruginosa [52,53]. The disc diffusion method was followed by 250μg/mL concentration with Ciprofloxacin taken as the standard.

2.3.2. Measurement of Antifungal Sensitivity Assay

Antifungal sensitivity have been analysed using Kirby Bauer [39] disc diffusion technique, PDA [54] medium was prepared and pasteurized as above. About 1 ml of the fungal species taken in a Petri-plate then PDA medium is poured (ear bearing heating condition).

The fungal sensitivities of all the synthesized (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one compounds have been analysed against fungal species A.niger [55], M.specie [56] and T.viride [57].

The species are spreading uniformly over the plates using clockwise and anti-clockwise rotations. The test compound solution has been prepared by dissolving 15mg of the chalcones in 1ml of DMSO solvent. The discs have been impregnated by test compound solution. The medium have been permitted to solidify and kept for 24 hours [58].

3. Results and Discussion

The authors have synthesized some (E)-3-(5-bromo- thiophen-2-yl)-1-phenylprop-2-en-1-ones using simple Crossed-Aldol condensation by stirring 5-bromothiophene-2-carbaldehyde (100 mmol) and ortho, meta and para substituted acetophenones (100mmol) and aqueous sodium hydroxide (200 ml 0.5M) in presence of absolute ethyl alcohol for 30 minutes. In this synthetic method, there is no product obtained stirring of the reactants less than 30 minutes. The obtained yield is more than 89%. The effect of substituents such as electron donating substituted acetophenones gave more yields than electron-withdrawing substituted acetophenones. The authors have obtained maximum yield (97%) for 3-methoxy substituents and minimum (89%) for 4-chloro substituents. These synthesised chalcones have been confirmed by their physical constants, elemental analysis and spectral data. The physical constants, analytical and micro analysis data of these (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one were showed in Table (1). The spectral data of synthesized substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones are showed in Table (2) and Table (3). From infrared spectra, the carbonyl stretching band of all ketones appears at 1850-1650 cm-1. The CO cis frequencies obtained within the range of 1653-1666 cm-1. Thee COtrans frequencies obtained within the range of 1581-1597 cm-1. The proton NMR chemical shift(d, ppm) values are obtained for Hα and Hβ in 7 ppm to 8 ppm. The 13C NMR Chemical shift values are obtained for CO in 170 ppm to 190 ppm, Cα and Cβ in 120 ppm to 140 ppm. These data are supported for confirmation of synthesized chalcones.

3.1. Antibacterial Activity

The antibacterial screening effect of synthesized (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one compounds are gives in Figure 2 (Plates 1 – 20). The inhibition zone values are used to compare in Table 4 and the corresponding clustered column chart is give in Figure  3.

Chalcone 9 showed good antibacterial activity against S. aureus strain. The unsaturated ketones 2-4, 7, 8 and 11 showed highly satisfactory activity against S. aureus strain. The chalcones 1, 5, 6 and 10 have no antibacterial activity against the S. aureus strain. Here the methyl group substituent enhances the antibacterial activity. The electron with-drawing halogens and electron donating methyl groups were slightly reduced the antibacterial activity against S. aureus strain. The polar and inductive effects of parent ketone and the electron-withdrawing 4-Cl, 4-F and 3-NO2 groups not showed the antibacterial activity against S. aureus strain.

The parent chalcone 1 showed good antibacterial activity against S. Pyogenes strain. Here the electronic effects such as polar, inductive, field and resonance effects of parent compound enhance the antibacterial activity against S. Pyogenes strain.

Figure 2. Antibacterial sensitivities of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones.

Table 4. Antibacterial activity of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones.

Entry X mm zone of inhibition
Gram +ve bacteria
S. Aureus S. Pyogenes M. Luteus B Substilis
1 H 0 8 6 7
2 3-Br 6 7 0 6
3 4-Br 6 7 6 6
4 3-Cl 6 6 6 6
5 4-Cl 0 0 0 0
6 4-F 0 0 0 0
7 3-OCH3 6 7 6 7
8 4-OCH3 6 7 7 0
9 4-CH3 7 6 6 6
10 3-NO2 0 0 6 6
11 4-NO2 6 6 6 6
Standard Ciprofloxacin 8 12 13 13
Control DMSO 0 0 0 0

Table 4. Continue.

Entry mm zone of inhibition
Gram +ve bacteria          
K. Pneumoniae V. Cholerae K. Oxytoca P. Mirabilis E. Coli P. Aeruginosa
1 7 6 6 6 7 6
2 7 8 8 6 0 0
3 6 6 7 7 0 6
4 8 6 6 7 0 7
5 7 6 0 0 6 6
6 6 6 0 6 6 0
7 6 0 6 6 6 7
8 7 7 7 7 8 6
9 6 0 8 6 7 7
10 6 6 6 0 6 0
11 6 6 6 6 7 6
Standard 10 8 13 9 11 11
Control 0 0 0 0 0 0

Figure 3. Antibacterial activities of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one compounds-clustered column chart.

The inductive and field effects of ketones containing electron with-drawing 3-Br, 4-Br (2, 3) and the resonance and conjugation effect of electron donating methoxy substituents 8 showed satisfactory antibacterial activity against S. Pyogenes strain. The chalcones 4, 9 and 11 have shown minimum antibacterial activity against S. Pyogenes strain. Here the inductive, field, polar, resonance and conjugative effects of electron withdrawing 3-Cl, 4-NO2 and methyl substituents reduced to minimum activity. The ketones 5, 6 and 10 have no antibacterial activity against S. Pyogenes strain. The polar, inductive, field and resonance effects of 4-Cl, 4-F and 3- NO2 substituents completely vanished the antibacterial activity against S. Pyogenes strain.

The chalcone (8) 4-OCH3 substituted shows satisfactory antibacterial activity against M. Luteus strain. The ketones (1, 3, 4, 7, 9, 10 and 11) containing electron with-drawing and electron donating substituents such as H, 4-Br, 3-Cl, 3-OCH3, 4-CH3, 3-NO2 and 4-NO2 substituents shows less satisfactory antibacterial activity against M. Luteus strain. Here the electronic effects such as polar, inductive, field and resonance effects of parent compound reduces the antibacterial activity against antibacterial activity against M. Luteus strain. The unsaturated ketones (2, 5 and 6) containing electron withdrawing substituents such as 3-Br, 4-Cl and 4-F had no antibacterial activity against M. Luteus strain. The inductive, polar and field effects of ketones completely vanished the antibacterial activity against M. Luteus strain.

The chalcones (1 and 7) H and 3-OCH3 substituted shows satisfactory antibacterial activity against B. Substilis strain. The parent and the resonance effects of the electron-donating methoxy groups shows satisfactory activity. The ketones (2-4, and 9-11) containing electron with-drawing and electron donating substituents such as 3-Br, 4-Br, 3-Cl, 3- NO2, 4-NO2, and 4-CH3 substituents shows less satisfactory antibacterial activity against B. Substilis strain. Here the electronic effects such as polar, inductive, field and resonance effects of parent compound reduces the antibacterial activity against antibacterial activity against B. Substilis strain. The unsaturated ketones (5, 6 and 8) containing electron with-drawing and electron donating substituents such as 4-Cl, 4-F and 4-OCH3 had no antibacterial activity against B. Substilis strain. The inductive, polar, resonance and field effects of ketones completely vanished the antibacterial activity against B. Substilis strain.

All synthesized chalcones (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones showed good antibacterial activity against the gram negative K. Pneumoniae bacterial strain. Here the electronic effects such as polar, inductive, field, conjugation and resonance effects of compounds operates normal antibacterial activity against K. Pneumoniae strain.

The ketone (2) containing 3-Br substituent showed excellent antibacterial activity against V. Cholerae strain. The inductive, polar, field and inductive effect of the substituent enhances the antibacterial activity against V. Cholerae strain. The (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones (1, 3-6, 8, 10 and 11) containing electron-withdrawing and electron donating substituents such as H, 4-Br, 3-Cl, 4-Cl, 4-F, 4-OCH3, 3-NO2 and 4-NO2 showed good antibacterial activity against V. Cholerae bacterial strain. Here the electronic effects such as polar, inductive, field, conjugation and resonance effects of substituents operates normal antibacterial activity against V. Cholerae strain. The unsaturated ketones (7 and 9) shows no antibacterial activity against V. Cholerae strain. The absence of resonance and hyper conjugative effects of 3-OCH3 and 4-CH3 substituents completely reduced the antibacterial activity against V. Cholerae bacterial strain.

The ketones (2, 3, 8 and 9) containing electron with-drawing and electron donating 3-Br, 4-Br, 3-OCH3 and 4-CH3, substituents showed good antibacterial activity against K. Oxytoca strain. The inductive, polar, field, resonance and hyperconjugative effects of the substituent enhance the antibacterial activity against K. Oxytoca strain. The (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones (1, 4, 7, 10 and 11) containing electron-withdrawing and electron donating substituents such as H, 3-Cl, 3-OCH3 and 3-NO2 showed satisfactory antibacterial activity against K. Oxytoca bacterial strain. Here the electronic effects such as polar, inductive, field and resonance effects of substituents operates normal antibacterial activity against K. Oxytoca strain. The unsaturated ketones (5 and 6) show no antibacterial activity against K. Oxytoca strain. The absence of inductive and polar effects of 4-Cl and 4-F substituents completely reduced the antibacterial activity against K. Oxytoca bacterial strain.

The chalcones (1-4, 6-9 and 11) containing electron with-drawing and electron donating H, 3-Br, 4-Br, 3-Cl, 4-F, 3-OCH3, 4-OCH3, 4-CH3 and 4-NO2 substituents showed good antibacterial activity against P. Mirabilis strain. The inductive, polar, field, resonance and hyperconjugative effects of the substituent enhance the antibacterial activity against P. Mirabilis strain. The (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones (5 and 10) containing electron-withdrawing and electron donating substituents such as 4-Cl, and 3-NO2 showed no antibacterial activity against P. Mirabilis bacterial strain. The absence of inductive and polar effects of the substituents completely reduced the antibacterial activity against P. Mirabilis bacterial strain.

The (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones (1 and 5-11) containing electron with-drawing and electron donating H, 4-Cl, 4-F, 3-OCH3, 4-OCH3, 4-CH3, 3-NO2 and 4-NO2 substituents showed good antibacterial activity against E. Coli strain. The inductive, polar, field, resonance and hyperconjugative effects of the substituent enhance the antibacterial activity against E. Coli strain. The chalcones (2-5) containing electron-withdrawing substituents such as 3-Br, 4-B4, and 3-Cl showed no antibacterial activity against E. Coli bacterial strain. The absence of inductive, field and polar effects of the substituents completely reduced the antibacterial activity against E. Coli bacterial strain.

The (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones (1, 3-5, 7-9 and 11) containing electron with-drawing and electron donating H, 4-Br, 3-Cl, 4-Cl, 3-OCH3, 4-OCH3, 4-CH3 and 4-NO2 substituents showed good antibacterial activity against P. Aeruginosa strain. The inductive, polar, field, resonance and hyperconjugative effects of the substituent enhance the antibacterial activity against P. Aeruginosa. The chalcones (2, 6 and 5) containing electron-withdrawing substituents such as 3-Br, 4-F, and 3-NO2 showed no antibacterial activity against P. Aeruginosa bacterial strain. The absence of inductive, field and polar effects of the substituents completely reduced the antibacterial activity against P. Aeruginosa bacterial strain.

3.2. Antifungal Activity

The inhibition zone value of the plates has been examined and measured the diameters. The results have been recorded by the triplicate and repeating the same procedure. The antifungal sensitivities of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one compounds have been analyzed and are shown in Table 5. The disc diffusion Plates (21-26) are shown in Figure 4 and the inhibition zone values of the effect is given in the clustered column chart, shown in Figure 5.

Table 5. Antifungal activity of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones.

Entry X mm of zone of inhibition
A. Niger M. Species T.viride
1 H 6 6 0
2 3-Br 7 7 6
3 4-Br 7 6 0
4 3-Cl 0 0 0
5 4-Cl 0 0 0
6 4-F 6 0 0
7 3-OCH3 0 6 0
8 4-OCH3 0 6 0
9 4-CH3 0 6 6
10 3-NO2 6 7 7
11 4-NO2 6 6 0
Standard Ciprofloxacin 8 9 8
Control DMSO 0 0 0

The substituted (E)3-(5-bromo thiophen-2-yl)-1-phenylprop-2-en-1-ones (1-3, 6, 10 and 11) containing electron with-drawing H, 3-Br, 4-Br, 4-F, 3-NO2 and 4-NO2 substituents showed good antifungal activity against A. Niger strain. The inductive, polar and field effects of the substituent enhance the antifungal activity against A. Niger strain. The chalcones (4, 5 and 7-9) containing electron-withdrawing and electron donating substituents such as 3-Cl, 4-Cl and methoxy showed no antifungal activity against A. Niger strain. The absence of inductive, field, resonance and polar effects of the substituents completely reduced the antifungal activity against A. Niger strain.

The chalcones (1-3, and 7-11) containing electron with-drawing H, 3-Br, 4-Br, 3-OCH3, 4-OCH3, 4-CH3, 3-NO2 and 4-NO2 substituents showed good antifungal activity against M. Species strain. The inductive, polar, resonance, field and hyperconjugative effects of the substituent enhance the antifungal activity against M. Species strain.

Figure 4. Antifungal sensitivities of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one compounds.

Figure 5. Antifungal sensitivities of substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-one compounds-clustered column chart.

The chalcones (4-9) containing electron-withdrawing substituent such as 3-Cl, 4-Cl and 4-F shows no antifungal activity against M. Species strain. The absence of inductive, field and polar effects of the substituents completely reduced the antifungal activity against M. Species strain.

The unsaturated ketones (2, 9 and 10) containing electron with-drawing 3-Br, 4-CH3 and 3-NO2 substituents showed good antifungal activity against T. viride fungal strain. The inductive, polar, resonance, field and hyperconjugative effects of the substituent enhance the antifungal activity against T.viride strain. The chalcones (1, 3-8 and 11) containing electron-withdrawing substituents such as H, 4-Br, 3-Cl, 4-Cl, 4-F, 3-OCH3, 4-OCH3 and 4-NO2 substituents shows no antifungal activity against T.viride strain. The absence of inductive, field, resonance and polar effects of the substituents completely reduced the antifungal activity against T.viride strain.

4. Conclusions

There are eleven substituted (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones have been synthesized. They are characterized by their analytical, UV, FT-IR and NMR spectral data. The antimicrobial activities of all chalcones have been evaluated by disc diffusion method using antibacterial antifungal strains. Chalcone 9 showed good antibacterial activity against S. aureus strain. The parent chalcone 1 showed good antibacterial activity against S. Pyogenes strain. All synthesized chalcones (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones showed good antibacterial activity against the gram negative K. Pneumoniae bacterial strain. The ketone (2) containing 3-Br substituent showed excellent antibacterial activity against V. Cholerae strain. The ketones (2, 3, 8 and 9) containing electron with-drawing and electron donating 3-Br, 4-Br, 3-OCH3 and 4-CH3, substituents showed good antibacterial activity against K. Oxytoca strain. The chalcones (1-4, 6-9 and 11) containing electron with-drawing and electron donating H, 3-Br, 4-Br, 3-Cl, 4-F, 3-OCH3, 4-OCH3, 4-CH3 and 4-NO2 substituents showed good antibacterial activity against P. Mirabilis strain. The (E)-3-(5-bromothiophen-2-yl)-1-phenyl prop-2-en-1-ones (1 and 5-11) containing electron with-drawing and electron donating H, 4-Cl, 4-F, 3-OCH3, 4-OCH3, 4-CH3, 3-NO2 and 4-NO2 substituents showed good antibacterial activity against E. Coli strain. The (E)-3-(5-bromothiophen-2-yl)-1-phenylprop-2-en-1-ones (1, 3-5, 7-9 and 11) containing electron with-drawing and electron donating H, 4-Br, 3-Cl, 4-Cl, 3-OCH3, 4-OCH3, 4-CH3 and 4-NO2 substituents showed good antibacterial activity against P. Aeruginosa strain. The substituted (E)3-(5-bromo thiophen-2-yl)-1-phenylprop-2-en-1-ones (1-3, 6, 10 and 11) containing electron with-drawing H, 3-Br, 4-Br, 4-F, 3-NO2 and 4-NO2 substituents showed good antifungal activity against A. Niger strain. The chalcones (1-3, and 7-11) containing electron with-drawing H, 3-Br, 4-Br, 3-OCH3, 4-OCH3, 4-CH3, 3-NO2 and 4-NO2 substituents showed good antifungal activity against M. Species strain. The unsaturated ketones (2, 9 and 10) containing electron with-drawing 3-Br, 4-CH3 and 3-NO2 substituents showed good antifungal activity against T. viride fungal strain.

Acknowledgement

The authors thank SAIF, IIT Chennai-600 036, for recording all the NMR spectra.


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