Synthesis, Antibacterial and Antioxidant Activity of 3-(5-Aryl)-1-(3-nitrophenyl) prop-2-en-1-one

 

Samina Aslam1,2*, Samia Khakwani1, 2, Nadia Asif1, Tahira Saleem1, Tehseen Gull1,Misbahul Ain Khan2,3

1Department of Chemistry, The Women University Multan, Multan, Pakistan

2Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

3Research and Development Labs, Shafi Reso, Ferozepur Road, Lahore, Pakistan

*Corresponding Author E-mail: drsamina.chem@wum.edu.pk

 

ABSTRACT:

Various chalcones with 3-nitro acetophenone were synthesized, characterized and screened for their antibacterial and antioxidant activities. The synthesized compounds were characterized through elemental analysis and spectroscopic techniques (FTIR, 1H NMR, 13C-NMR and Mass).All the compound of these series showed better results as compared with the standard.

 

KEYWORDS: Chalcone, Antioxidant Activity, Antibacterial Activity, Claisen Schmidt reaction

 

 

INTRODUCTION:

Compounds with chalcone as backbone have been reported to exhibit variety of pharmacological effects, including antioncogenic, anti-inflammatory1-2, antiulcerative, analgesic, antiviral, antimalarial3, antifungal, antioxidant,4 anti-leishmanial5 and antibacterial activities6. The presence of a reactive α,β-unsaturated keto function in chalcones is found to be responsible for their antimicrobial activity, which may be altered depending on the type and position of the substituent on the aromatic rings.7-8.

(A)

X= NH, O, N-CH3, Y= NH, O, N-CH3, A= CH (CH3), CH2CH (CH3), R= H, t-C4H9

 

(B)

R= OH, OCH3, N(CH3)2

 

 (C)

R1, R2, R3, R4= OH, H, Br, I, Me, OMe, NH2  , Cl

 

EXPERIMENTAL:

General

All reagents and solvents were used as obtained from the supplier or recrystallized or redistilled as necessary. Thin Layer chromatography was performed using aluminium sheets (Merck) coated with silica gel 60 F254. IR spectra were recorded by using an IR Perkin-Elmer Spectrum 1 FTIR spectrophotometer and peaks are reported max (neat)/cm-1 which refer to the min wave numbers. Proton magnetic resonance spectra were recorded in CDCl3 with Bruker AM 300 spectrometers (Rheinstetten–Forchheim, Germany) operating at 300 MHz, respectively. The 13C NMR spectra were recorded in CDCl3 with Bruker AM 100 spectrometer operating at 100 MHz. Tetramethyl-silane was used as an internal standard. Elemental analysis for C, H and N were recorded with Perkin-Elmer 2400 Series II CHN Analyzer. Melting points were recorded on a GallenKamp apparatus and are uncorrected.

 

General procedure for the synthesis of 5-arylfuran 2-carbldehydes:

These were prepared as described in an earlier publication.9

 

General procedure for the synthesis of Chalcones:

Equimolar quantities of an arylfuran-2-carbaldehyde and 3-nitro acetophenone was taken in  ethanol and water mixture(10mL ethanol + 10mL water) in the presence of NaOH as a catalyst in ice bath(  -50C) and  the mixture was stirred for 4 hours. Solid product formed was filtered, dried and recrystallized from ethanol

 

1-(3'-nitrophenyl-3-[5-(4''-chlorophenyl)-2-furyl]-2-propen-1-one9 (1)

Yield: 2.5 g (81%)M.P:  146°C FTIR (KBr) (v, cm-1): 2365.82 (Aromatic ring), 1653.92 (C=O conjugated carbonyl group), 1589.92 (C=C conjugated), 1527.82 and 1350.38 (Asym and sym -NO2), 1090.65 (C-Cl bond), Mass spectra m/z (%):355 [M++2] (38), 353  [M+]  (100) , 318 [M+-Cl] (16),  306 [M+-NO2] (4), 272 [M+-NO2-Cl] (4), 242 [M+-PhCl] (15), 231 [M+-PhNO2] (23),  150  [PhCONO2]  (11), 111 [PhCl] (4),    1H-NMR (CDCl­3): δ: 8.855 (1H, s, Ar-H), 8.440 (1H, d, J = 2.7, Ar-H), 8.373 (1H, d, J = 2.7, Ar-H), 7.729 (1H, t, J = 5.7, Ar-H), 7.651 (1H, d, J = 2.7, Ar-H), 7.477 (1H, d, J = 16.5, ethylenic), 7.425(1H, d, J = 6.3, Ar-H), 7.404(1H, d, J = 16.5, ethylenic), 7.345 (1H, d, J = 6.3, Ar-H), 7.241 (1H, d, J = 6.3, Ar-H), 6.890 (1H, d, J = 2.7, furyl proton), 6.800 (1H, d, J = 2.7, furyl proton) 13C-NMR (CDCl­3): δ: 186.90 (C=O), 130.65, 127.22 (C=C), 154.98, 150.95, 148.21, 138.79, 134.63, 133.33, 131.20, 129.11, 128.97, 128.04, 126.20, 125.22, 122.64, 120.87, 110.12, 109.11 (Ar-C)  Anal.Calcd.for C19H12ClNO4: C 64.58; H 3.40; N 3.96 %. Found C 64.61; H 3.32; N 3.89 %.

 

1-(3'-nitrophenyl-3-[5-(2''-nitro-4''-chlorophenyl)-2-furyl]-2-propen-1-one (2)

Yield: 2.6 g (82%)M.P:  188°C FTIR (KBr) (v, cm-1): 2362.06 (Aromatic ring), 1660.04 (C=O conjugated carbonyl group), 1604.42 (C=C conjugated), 1529.17 and 1352.44 (Asym and sym -NO2), 1091.91 (C-Cl bond),Mass spectra m/z (%):400 [M++2] (12),  398  [M+]  (4),  248 [M+-PhCONO2] (4),  189 [furylPhNO2]  (39) , 150  [PhCONO2]  (94) , 76  [ Ph]  (100),  1H-NMR (CDCl­3): δ: 8.852 (1H, s, Ar-H), 8.441 (1H, d, J = 6, Ar-H), 8.353 (1H, d, J = 6, Ar-H), 7.753 (1H, d, J = 16.9, ethylenic), 7.694 (1H, d, J = 16.9, ethylenic), 7.642 (1H, s, Ar-H ), 7.620 (1H, d, J = 1.5, Ar-H), 7.604 (1H, d, J = 1.5, Ar-H), 7.548 (1H, t, J = 1.5, Ar-H), 6.864 (1H, d, J = 2.7, furyl proton), 6.802 (1H, d, J = 2.7, furyl proton) 13C-NMR (CDCl­3): δ: 187.66 (C=O), 131.38, 127.23 (C=C), 153.21, 151.97, 151.31, 136.42, 131.86, 131.66, 130.40, 130.35, 128.18, 127.32, 123.56, 119.29, 119.10, 114.38 (Ar-C) Anal. Calcd.for C19H11 ClN2O6: C 57.28; H 2.76; N 7.03%.  Found C 56.88; H 2.47; N 6.83%.

 

1-(3'-nitrophenyl-3-[5-(3''-nitrophenyl)-2-furyl]-2-propen-1-one    (3)

Yield: 2.3 g (78%)M.P:  168-70°C FTIR (KBr) (v,   cm-1): 2369.99 (Aromatic ring) 1653.92 (C=O conjugated carbonyl group), 1593.26 (C=C conjugated), 1560.52 and 1351.64 (Asym and sym -NO2), Mass spectra m/z (%):  364  [M+]  (100) , 242 [M+-PhNO2] (79), 215 [furylPhNO2CH=CH]  (20) , 203 [furylPhNO2CH]  (26 ), 189 [furylPhNO2]  (15), 168 [furylPhCH=CH]  (16) ,  150  [PhCONO2]  (39), 76  [ Ph]  (33),  1H-NMR (CDCl­3): δ: 8.900 (1H, s, Ar-H), 8.600 (1H, d, J = 6, Ar-H), 8.400 (1H, d, J = 6, Ar-H), 8.301 (1H, d, J = 16.5, ethylenic), 7.694 (1H, d, J = 16.5, ethylenic), 7.642 (1H, s, Ar-H), 7.620 (1H, d, J = 1.5, Ar-H), 7.604 (2H, d, J = 2.7, Ar-H), 7.548 (1H, d, J = 2.7, furyl proton), 6.970 (1H, d, J = 2.7, furyl proton)13C-NMR (CDCl­3): δ: 188.58 (C=O), 132.84, 129.63, (C=C) 152.45, 149.62, 146.46, 137.31, 133.31, 129.53, 129.04, 128.87, 128.46, 126.04, 122.56, 121.19, 119.12, 117.18 (Ar-C) Anal.Calcd.for C19H12 N2O6: C 62.63; H 3.29; N 7.69%.  Found C 62.19; H 3.41; N 6.90%.

 

1-(3'-nitrophenyl-3-[5-(2'', 4''-dichlorophenyl)-2-furyl]-2-propen-1-one (4)

Yield: 2.2 g (76%)M.P:  158-60°C FTIR (KBr) (v,   cm-1): 2359.73 (Aromatic ring), 1652.13 (C=O conjugated carbonyl group), 1588.29(C=C conjugated), 1573.47 and 1345.76 (Asym and sym -NO2), 1086.19(C-Cl bond), Mass spectra m/z (%): 389 [M++2] (38), 387  [M+]  (100), 352 [M+- Cl]  (15), 265  [M+- PhNO2]  (25), 242 [M+- PhCl2]  (30) , 150 [PhCONO2] (9),  111  [PhCl]  (51), 76  [ Ph]  (19), 1H-NMR (CDCl­3): δ: 8.753 (1H, s, Ar-H), 8.593 (1H, d, J = 5.7, Ar-H), 8.508 (1H, d, J = 5.7, Ar-H), 8.205 (1H, d, J = 6.3, Ar-H), 7.907 (1H, d, J = 15, ethylenic), 7.817 (1H, d, J = 15, ethylenic), 7.415 (1H, d, J = 2.7, furyl proton), 7.314 (1H, d, J = 2.7, furyl proton) 7.714 (1H, s, Ar-H), 7.676 (2H, s, Ar-H)13C-NMR (CDCl­3): δ: 188.17(C=O), 132.09, 129.89, (C=C), 156.93, 152.72, 149.40, 146.86, 140.39, 139.43, 136.29, 135.00, 134.74, 133.91, 129.72, 129.55 124.22, 120.09, 117.90, 112.74   (Ar-C)  Anal.Calcd.for C19H11Cl2 NO4: C 58.91; H 2.84; N 3.61%.  Found C 58.68; H 2.61; N 3.48%.

 

1-(3'-nitrophenyl-3-[5-(2''-chlorophenyl)-2-furyl]-2-propen-1-one (5)

Yield: 2.4 g (78%)M.P:  138-40°C FTIR (KBr) (v,   cm-1): 2337.94 (Aromatic ring), 1659.15(C=O conjugated carbonyl group), 1586.20 (C=C conjugated), 1519.39 and 1355.06 (Asym and sym -NO2), 1089.22 (C-Cl bond), Mass spectra m/z (%):355 [M++2] (20), 353  [M+]  (61),  272  [ M-Cl-NO2]  (58) , 242  [M+- PhCl]  (38), 231  [M+- PhNO2]  (36), 175  [ PhNO2COCH=CH]  (19), 149  [ PhNO2CO]  (41),  111  [PhCl]  (25), 76  [ Ph]  (58), 1H-NMR (CDCl­3): δ: 8.851-7.462 (8H, m, Ar-H), 7.380 (1H, d, J = 15.7, ethylenic), 7.306 (1H, d, J = 15.7, ethylenic), 7.210 (1H, d, J = 2.2, furyl proton), 6.932 (1H, d, J = 2.2, furyl proton) 13C-NMR (CDCl­3): δ: 186.97 (C=O), 131.09, 127.38(C=C), 152.09, 150.69, 148.16, 138.67, 134.58, 130.92, 130.62, 130.02, 129.68, 128.73, 127.70, 127.19, 122.63, 120.03, 118.86, 114.14 (Ar-C), Anal.Calcd.for C19H12ClNO4: C 64.58; H 3.39; N 3.96%.  Found C 64.12; H 2.96; N 3.53%.

 

1-(3'-nitrophenyl-3-[5-(4''-bromophenyl)-2-furyl]-2-propen-1-one (6)

Yield: 2.5 g (80%)M.P:  156-60°C FTIR (KBr) (v,   cm-1): 2359.78 (Aromatic ring) 1651.42(C=O conjugated carbonyl group), 1589.25(C=C conjugated), 1526.37 and 1351.70 (Asym and sym -NO2), 1028.44 (C-Br bond), Mass spectra m/z (%): 399 [M++2] (55), 397 [M+] (53), 351 [M+- NO2] (10), 318 [M+- Br] (40), 275 [M+- PhNO2] (32), 242 [M+- PhBr] (38), 150 [PhNO2CO] (60), 76 [Ph] (100)   1H-NMR (CDCl­3): δ: 8.853 (1H, s, Ar-H), 8.441 (1H, d, J = 5.7, Ar-H), 8.372 (1H, d, J = 5.7, Ar-H), 7.731 (1H, d, J = 15.5, ethylenic), 7.350 (4H, m, Ar-H), 7.580 (1H, d, J = 15.5, ethylenic), 7.494 (1H, d, J = 5.7, Ar-H), 6.887 (1H, d, J = 2.4, furyl proton), 6.813 (1H, d, J = 2.4, furyl proton) 13C-NMR (CDCl­3): δ: 186.91 (C=O), 131.17, 127.15(C=C) 155.00, 150.95, 148.19, 138.78, 134.56, 131.96, 128.33, 126.37, 122.59, 121.98, 120.76, 118.15, 110.13 (Ar-C),  Anal.Calcd.for C19H12BrNO4: C 57.43; H 3.02; N 3.52%.  Found C 56.96; H 2.48; N 2.79%.

 

1-(3'-nitrophenyl-3-[5-(2''-methyl-3''-nitrophenyl)-2-furyl]-2-propen-1-one (7)

Yield: 2.7 g (84%)M.P:  182-84°C FTIR (KBr) (v,   cm-1):  2360.10 (Aromatic ring), 1662.46 (C=O conjugated carbonyl group), 1593.43 (C=C conjugated), 1551.32 and 1351.64 (Asym and sym -NO2) Mass spectra m/z (%) : 378  [M+] (100),  214  [M+-164] (15) , 202  [M+-176] (80),  ,152 [PhNO2CO] (78), 91 [C7H7]  (28), 55 [COCH=CH]  (66) , 1H-NMR (CDCl­3): δ: 8.741(1H, s, Ar-H), 8.577(1H, d, J = 3.5, Ar-H), 8.143( d1H, d, J = 3.5, Ar-H), 7.883(1H, d, J = 5.7, Ar-H), 7.717(1H, d, J = 5.7, Ar-H),, 7.693 (1H, d, J = 3.3, Ar-H), 7.587(1H, d, J = 3.3, Ar-H), 7.957(1H, d, J = 14.8, ethylenic), 7.348 (1H, d, J = 14.8, ethylenic), 7.146(1H, d, J = 2.6, furyl proton), 7.137(1H, d, J = 2.6, furyl proton) 2.531 (3H, s, CH3) 13C-NMR (CDCl­3): δ: 187.00 (C=O), 131.12, 127.44(C=C), 16.40 (CH3), 155.60, 153.50, 152.08, 151.20, 148.16, 138.64, 134.50, 132.24, 131.68,130. 58 128.96, 128.21, 127.29, 124.44, 123.59, 122.58, 118.89, 113.61(Ar-C), Anal.Calcd.for C20H14N2O6: C 63.49; H 3.70; N 7.40 %. Found C 62.86; H 3.14; N 7.05%.

 

1-(3'-nitrophenyl-3-[5-(3'', 5''-dichlorophenyl)-2-furyl]-2-propen-1-one (8)

Yield: 2.1 g (75%)M.P:  196°C FTIR (KBr) (v, cm-1): 2358.85  (Aromatic ring) ,1660.11 (C=O conjugated carbonyl group), 1595.02 (C=C conjugated) , 1084.09  ( C-Cl bond), , 1567.13  and 1357.32 (Asym and sym  -NO2), Mass spectra m/z (%): 389 [M++2] (30), 387 [M+] (55), 352 [M+- Cl] (10), 267 [M++2-PhNO2] (15), 265 [M+- PhNO2] (25), 242 [M+- PhCl2] (35), 150 [PhNO2CO] (35), 104 [PhCO] (35), 139 [PhCOCl] (58), 76 [Ph] (100) 1H-NMR (CDCl­3): δ:  8.487(1H, s, Ar-H), 8.396 (1H, d, J = 2.7, Ar-H), 8.370(1H, d, J = 2.7, Ar-H), 8.217 (1H, d, J = 6.6, Ar-H), 7.926(1H, d, J = 6.6, Ar-H), 7.612 (1H, d, J = 6, Ar-H), 7.548(1H, d, J = 6, Ar-H), 7.495(1H, d, J = 6, Ar-H), 7.914(1H, d, J = 15.9, ethylenic), 7.459 (1H, d, J = 15.9, ethylenic), 7.295(1H, d, J = 2.8, furyl proton), 7.284 (1H, d, J = 2.8, furyl proton) 13C-NMR (CDCl­3): δ:  187.07 (C=O), 130.97, 127.24(C=C), 152.96, 151.69, 148.21, 138.67, 134.73, 132.36, 128.47, 127.80, 122.75, 122.69, 120.49, 119.18, 111.92 (Ar-C), Anal.Calcd.for C19H11Cl2NO4: C 58.91; H 2.84; N 3.61%.  Found C 58.68; H 2.79; N 3.55%.

 

1-(3'-nitrophenyl-3-[5-(2'', 4''-dinitrophenyl)-2-furyl]-2-propen-1-one (9)

Yield: 2.5 g (80%) M.P:  128°C FTIR (KBr) (v, cm-1): 2363.21(Aromatic ring), 1691.24 (C=O conjugated carbonyl group), 1582.54(C=C conjugated), 1545.30 and 1346.34 (Asym and sym -NO2), Mass spectra m/z (%): 409 [M+] (6), 242 [M+-167] (10),   233 [M+- 176] (2), 150 [PhNO2CO] (55), 76 [Ph] (100), 1H-NMR (CDCl­3): δ: 8.862-8.569 (7H, m, Ar-H), 8.224 (1H, d, J = 16.2, ethylenic), 7.724 (1H, d, J = 16.2, ethylenic), 7.453 (1H, d, J = 3.3, furyl proton), 7.441 (1H, d, J = 3.3, furyl proton) 13C-NMR (CDCl­3): δ:  178.67(C=O), 131.17, 127.13 (C=C), 154.67, 153.89, 150.99, 133.89, 128.78, 127.67, 124.08, 120.12, 115.01(Ar-C),  Anal.Calcd.for C19H11N3O8: C 55.74; H 2.69; N 10.26 %. Found C 55.04; H 2.53; N 10.29%.

 

1-(3'-nitrophenyl-3-[5-(2''-chloro-4''-nitrophenyl)-2-furyl]-2-propen-1-one (10)

Yield: 2.1 g (75%)M.P:  152-54°C FTIR (KBr) (v,   cm-1): 2363.34 (Aromatic ring), 1679.90 (C=O conjugated carbonyl group), 1578.54 (C=C conjugated), 1552.32 and 1344.23 (Asym and sym -NO2), 1094.03 (C-Cl bond) Mass spectra m/z (%): 400 [M++2] (31), 398 [M+] (100), 276 [M+-PhNO2] (32), 242 [M+-PhClNO2] (14), 150 [PhCONO2] (42), 76 [Ph] (48), 1H-NMR (CDCl­3): δ:  8.527-8.284 (8H, m, Ar-H), 7.927 (1H, d, J = 15.9, ethylenic), 7.702 (1H, d, J = 15.9, ethylenic), 7.420 (1H, d, J = 3.3, furyl proton), 7.407 (1H, d, J = 3.3, furyl proton)  13C-NMR (CDCl­3): δ:  178.92(C=O), 131.45, 127.98 (C=C), 155.67, 152.99, 149.69, 133.87, 128.70, 127.47, 124.08, 120.12, 118.75, 108.79(Ar-C),  Anal.Calcd.for C19H11ClN2O6: C 57.28; H 2.76; N 7.03%.  Found C 57.33; H 2.45; N 6.87%.

 

RESULTS AND DISCUSSIONS:

A series of structurally related chalcones were prepared according to Scheme 1 by reacting 5-arylfuran-2-carbaldehydes with 3-nitroacetophenone. All the reactions were carried out in ethanol in the presence of catalytic amount of sodium hydroxide.

 

 

Scheme 1

 

 

BIOLOGICAL ACTIVITIES:

Antioxidant activity

Garret nitric oxide (NO) scavenging method was used for the determination of antioxidant activity5. The method is based on the principle that nitrate present in the sample must be reduced to nitrite. This method involves the determination of nitrite, instead of nitrate in the presence of Griss reagent. A series of compounds is studied for their antioxidant activity, and showed significant activity. Compound having deactivating group like chaloro and bromo substituent showed good results as compared to the compound having nitro group. In this series compound 8 showed highest inhibition value in which two chloro group are present on the phenyl ring. While compound having chloro and nitro group on the same ring also showed good results, while compound having nitro group on the phenyl group showed significant activity.The results are presented in Table 1.

 

Table:1. Antioxidant activity of 5-Arylfuran-2-carbaldehyde Chalcones

Sr.

No

Structure

%age Inhibitions

1

 

15.8

2

 

8.9

3

 

7.0

4

 

28

5

 

31.1

6

 

24.1

7

 

30

8

 

36

9

 

26.5

10

 

22

 

Ascorbic acid

38.5

 

 

Antifungal Activity:

Agar Disc Diffusion Method:

Muller Hinton Agar plates were prepared and the test organisms were inoculated by the spread plate method. Filter paper discs approximately 6mm in diameter were soaked with 15µl of the sample and placed in the previously prepared agar plates. Each disc was pressed down to ensure complete contact with the agar surface and distributed evenly so that they are no closer than 24mm from each other, center to center. The agar plates were then incubated at 37Co. After 16-18 hours of incubation, each plate was examined. The resulting zones of inhibition were uniformlycircular with a confluent lawn of growth. The diameters of zones of complete inhibition were measured including the diameter of the disc of control.

 

Table 2 showed the results of antibacterial activity of 5-arylfuran-2-carbaldehyde chalcones which were subjected for % inhibition for four strains. All compounds showed comparable results with control value. The general trend is the enhancement of activity in the compounds having electron donating chloro and bromo group, while compound having electron withdrawing group on the phenyl ring showed significant results. In this series compound 6 and 7 showed highest inhibition value against S.Aurius while compound 1 and 8 showed good activity against E.Coli. Compound 1,4,5,8 are active against bacterial strain B.Subtillus and S. Typhae.

 

 

Table:2. Antibacterial  activity of 5-Arylfuran-2-carbaldehyde Chalcones

Compound no

Structure

%age Inhibitions

S.Arius

E.Coli

B.Subtilus

S.Typhae

1

 

    15

17

13

19

2

 

10

14

12

15

3

 

16

13

14

15

4

 

10

13

16

15

5

 

17

11

14

15

6

 

15

14

12

16

7

 

16

12

13

14

8

 

13

15

14

16

9

 

14

12

10

13

10

 

11

12

10

13

Control

Ciprofloxacin

21

19

20

22

 

 

CONCLUSIONS:

In this communication, we have presented antibacterial and antioxidant activities of 3-(5-Aryl)-1-(3-nitrophenyl) prop-2-en-1-one. These compounds showed significant activity against different strain of bacteria and standard.

 

ACKNOWLEDGEMENTS:

S.A. is thankful to the HEC Govt. Of Pakistan for an Interim placement fellowship and M.A.K. for the analytical support.

 

REFERENCES:

1.          Rani, P.; Srivastava, V. K.; Kumar, A., Synthesis and antiinflammatory activity of heterocyclic indole derivatives. European Journal of Medicinal Chemistry 2004, 39, 449-452.

2.          Sharma, P. K.; Kumar, S.; Kumar, P.; Kaushik, P.; Kaushik, D.; Dhingra, Y.; Aneja, K. R., Synthesis and biological evaluation of some pyrazolylpyrazolines as antiinflammatory–antimicrobial agents. European Journal of Medicinal Chemistry 2010, 45, 2650-2655.

3.          Tomar, V.; Bhattacharjee, G.; Rajakumar, K. S.; Srivastava, K.; Puri., S. K., Synthesis of new chalcone derivatives containing acridinyl moiety with potential antimalarial activity. European Journal of Medicinal Chemistry 2010, 45, 745-751.

4.          Biradar, J. S.; Sasidhar, B. S.; Parveen., R., Synthesis, antioxidant and DNA cleavage activities of novel indole derivatives. European Journal of Medicinal Chemistry 2010, 45, 4074-4078.

5.          Hussain, T.; Siddiqui, H. L.; Rehman, M. Z.; Yasinzai, M. M.; Parvez., M., Anti-oxidant, anti-fungal and anti-leishmanial activities of novel 3-[4-(1H-imidazol-1-yl) phenyl]prop-2-en-1-ones. European Journal of Medicinal Chemistry 2009, 44, 4654-4660.

6.          Solankee, A.; Kapadia, K.; iric, A. C.; Sokovic, M.; Doytchinova, I.; Geronikaki., A., Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents. European Journal of Medicinal Chemistry 2010, 45, 510-518.

7.          Prasad, Y. R.; Kumar, P. R.; Smiles, D. J.; Babu, P. A., QSAR studies on chalcone derivatives as antibacterial agents against Bacillus pumilis. Arkivoc 2008 11, 266-276.

8.          Aichaoui, H.; Guenadi, F.; Kapanda, C. N.; Lambert, D. M.; McCurdy, C. R.; Poupaert., J. H., Synthesis and pharmacological evaluation of antioxidant chalcone derivatives of 2(3H)-benzoxazolones. Medicinal Chemistry Research 2009, 18, 467-476.

9.          Aslam, S.; Asif, N.; Khan, M. N.; Khan, M. A.; Munawar, M. A.; Nasrullah., M., Synthesis of novel arylfurylchalcones. Asian Journal of Chemistry 2013, 25, 7738-7741.

 

 

 

Received on 24.07.2016         Modified on 14.08.2016

Accepted on 21.08.2016         © AJRC All right reserved

Asian J. Research Chem. 9(10): October 2016; Page 435-440

DOI: 10.5958/0974-4150.2016.00065.1