Dibenzalketones December 2017

IJRPC 2017, 7(4), 585-606 Kundavaram Raju et al ISSN: 22312781
INTERNATIONAL JOURNAL OF RESEARCH IN PHARMACY AND CHEMISTRY
Available online at www.ijrpc.com Research Article
SYNTHESIS AND ANTI-OXIDANT

ACTIVITY OF DIBENZALKETONES
Kundavaram Raju*, Joseph Vinod and Sirisha Mulukuri
Karnataka College of Pharmacy, Bangalore, Karnataka, India.
ABSTRACT
Antioxidant activity which plays key role for detecting the compounds whether they have affinity
towards various types of cancer cells and other related chronic diseases. Hence we felt worthwhile to
study in detail about the antioxidant activity of some synthesized compounds. As chalcones have
numerous pharmacological actions towards various disease we focused on the α, β-unsaturated keto
function in chalcones, which gives impetus to synthesize different Dibenzalketone derivatives and to
test the compounds for antioxidant activity.
1. INTRODUCTION
Chalcone is an aromatic ketone that forms the central core for a variety of important biological
compounds. Chalcone can be prepared by an aldol condensation between a aldehyde and an ketone
1
in the presence of a catalyst. Aldol condensation is also known as Claisen-Schmidt rection .The aldol
2
reaction is one of the most powerful methods available for forming a carbon-carbon bond . In this
reaction, the conjugate base of an aldehyde or ketone adds to the carbonyl group of another aldehyde
or ketone to give a β-hydroxyaldehyde or β-hydroxyketone product.
There are several methods available for the synthesis of chalcones. The most widely used is the
3 4
base-catalyzed such as sodium hydroxide (NaOH) , potassium hydroxide (KOH) , barium hydroxide
5 6
Ba(OH)2 , and lithium hydroxide (LiOH.H2O) . The acid-catalyzed that had been used to synthesize
7 8 9
chalcones includes aluminum trichloride (AlCl 3) , dry HCl , boron trifluoride-etherate (BF3-Et2O) ,
10 11 12
titanium tetrachloride (TiCl4) and ruthenium trichloride (RuCl3) . Chalcones show antimicrobial ,
13 14 15 16, 17
antimalarial , anticancer , antioxidant and anti-inflammatory and antitubercular properties.The
presence of a reactive α, β-unsaturated keto function in chalcones was found to be responsible for
their antimicrobial activity. Recently, more attention has been paid to the synthesis of α, α’-
18,19
bis(substituted benzylidene) cycloalkanones are known as the dibenzalketone derivatives. These
derivatives can be prepared by the crossed aldol condensation of cycloalkanones with aldehydes and
ketones. Different complexes of metal ions such as Mn(II), Fe(II), Co(II), Ni(II),cu(II) and Zn(II) with
20
different ligands have been used for aldol condensation . There are several methods available for the
synthesis of dibenzalketones. Some of them are: Bis(p-methoxy-phenyl)telluroxide and KF-Al2O3 have
been used for crossed-aldol condensation of cycloalkanones with aromatic aldehydes under
21,22
microwave irradiation . Anhydrous RuCl, and TiCl3(SO3CF3) have also been used for this purpose
23,24
under solvent free conditions . Dibenzalacetone has a conjugated system and is expected to be
25
easilyoxidized .The more the double bond, the easier it will be oxidized. Therefore, it is assumed that
Dibenzalacetone and its derivatives will show antimicrobial and antioxidant activity.
R1 R1
R2 R2
General Structure of Dibenzalketone
585
2. EXPERIMENT POSTULATION
CHO
O
1 H3C CH3 + 2
R
propan-2-one benzaldehyde
0
20 c NaOH + Ethanol
R R
R = CHO- Benzaldehyde
R = Cl - 4- Chloro enzaldehyde
R = NO2 - 4-Nitro benzaldehyde
R = MeO- 4-Methoxy benzaldehyde
O
O
2 H
1 H3C CH3 +
propan-2-one 3-phenylpropanal
0
20 c NaOH + Ethanol
(1E,3E,6E,8E)-1,9-diphenylnona-1,3,6,8-tetraen-5-one
586
O CHO
1 + 2
R
cyclohexanone
0
20 c NaOH + Ethanol
R R
R = CHO- Benzaldehyde
R = Cl - 4-Chloro benzaldehyde
R = NO2- 4-Nitro benzaldehyde
R = MeO- 4-Methoxy benzaldehyde
O O
H
1 + 2
cyclohexanone 3-phenylpropanal
200c NaOH-Ethanol mixture
(2E,6E)-2,6-bis[(2E)-3-phenylprop-2-en-1-ylidene]cyclohexanone
587
3. EXPERIMENTAL SECTION
Preparation of 1,5-diphenylpenta1,4-dien-3-one
Reaction:
CHO O
O 0
20 C
1 2
H3C CH3 + NaOH-Ethanol mixture
propan-2-one benzaldehyde (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one

M. F - C3H6O M.F -C7H6O M.F - C17H14O
M.W - 58 M.W – 106 M.W - 234
Procedure
Prepare an ice-water bath in a 250ml beaker, place 15ml of ethanol and 20ml of aqueous 10%
NaOHinto a 100 ml beaker & add a stirbar. Place the 100ml beaker into the ice-water bath. Set then
the entire assembly on to a magnetic stirrer. While stirring, cool the solution to 20°c. After the solution
reaches to 20°c, remove the ice-water bath, continue to stir the solution.
Prepare the mixture of 2.1 ml (2 m mol) of fresh Benzaldehyde and 758 µl (1 m mol) of Acetone in a
test tube over a period of 5-10 mins, add the Benzaldehyde-acetone mixture to the ethanol-NaOH
solution in a small portions, then stir the reaction for another 30 mins. Cool the mixture using the ice
water bath for one hour. collect the crystals by vaccum filtration. Wash the crystals by suspending
them in 50ml of distil water. Again collect the crystals by vaccum filtration. Finally recrystalised with
ethyl acetate.
Check the filtrate by testing the last few drops of water using red-litmus paper. If the litmus changes to
blue, wash the crystals again until red-litmus does not changes colour. Keep a small sample aside to
56
dry for a crude melting point measurement .
TLC studies
1: starting material (1)

2: co-spot (1& 1a)
3: product (1a)
1 2 3 Rf values
Mobile phase :Benzene:Methanol (9:1)
Rf value of the product : 0.87
Rfvalue of the product : 0.91
Percentage yield : 82%
588
Preparation of 1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one
Reaction
CHO O
O 0
20 C
1 H3C CH3 + 2
NaOH-Ethanol mixture
Cl Cl
Cl
propan-2-one 4-chlorobenzaldehyde (1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one
M. F - C3H6O M.F -C5H3ClO M.F - C17H12Cl2O

M.W - 58 M.W -140 M.W - 303
Procedure
Prepare the mixture of 2.8ml (2m mol) of fresh 4-Chloro benzaldehyde and 758µl (1 m mol) of
Acetone in a test tube over a period of 5-10 mins, add the 4-Chloro benzaldehyde-acetone mixture to
the ethanol-NaOH solution in a small portions, then stir the reaction for another 30 mins. Cool the
mixture using the ice water bath for one hour. Collect the crystals by vaccum filtration. Wash the
crystals by suspending them in 50ml of distil water. Again collect the crystals by vaccum filtration.
Finally recrystalised with ethyl acetate.
56
TLC studies

2: co-spot (1& 1b)
3: product (1b)
1 2 3 Rf values
Mobile phase : Benzene : Methanol (9:1)
Rfvalue of the starting material : 0.89
589
Preparation of (1e, 4e)-1,5-bis(4-nitrophenyl)penta-1,4-dien-3-one:

Reaction
CHO O
O 0
20 C
1 H3C CH3 + 2
O 2N NO 2
O 2N
propan-2-one 4-nitrobenzaldehyde (1E,4E)-1,5-bis(4-nitrophenyl)penta-1,4-dien-3-one
M. F - C3H6O M.F - C6H4NO2 M.F - C17H12N2O5

M.W – 58 M.W -151 M.W - 324.
Procedure
Prepare the mixture of 2.1ml (2 m mol) of fresh 4-Nitro benzaldehyde and 758µl (1m mol) of Acetone
in a test tube over a period of 5-10 mins, add the 4-Nitro benzaldehyde-acetone mixture to the
ethanol-NaOHsolution in a small portions, then stir the reaction for another 30 mins. Cool the mixture
using the ice water bath over night, collect the crystals by vaccum filtration. Wash the crystals by
suspending them in 50ml of distil water. Again collect the crystals by vaccum filtration. Finally
recrystalised with ethyl acetate.
56
TLC studies

2: co-spot (1& 1c)
3: product (1c)
1 2 3 Rf values
Mobile phase: Benzene : Methanol (9:1)
Rf value of the starting material : 0.91
590
Preparation of (1e, 4e)-1, 5-bis(4-methoxyphenyl)penta-1,4-dien-3-one:

Reaction
CHO O
O
0
20 C
1 H3C CH3 + 2
H3CO OCH 3
H3CO
propan-2-one 4-methoxybenzaldehyde (1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one

M. F - C3H6O M.F - C8H8O2 M.F - C19H18O3
M.W -58 M.W - 136 M.W - 294
Procedure
Prepare an ice - water bath in a 250ml beaker, place 15ml of ethanol and 20ml of aqueous 10%
Prepare the mixture of 2.8ml (2 m mol) of fresh 4-Methoxy benzaldehyde and 758µl(1 m mol) of
Acetone in a test tube over a period of 5-10 mins, add the 4-Methoxy benzaldehyde-acetone mixture
to the ethanol-NaOH solution in a small portions, then stir the reaction for another 30 mins. Cool the
mixture using the ice water bath overnight. Collect the crystals by vaccum filtration. Wash the crystals
by suspending them in 50ml of distil water. Again collect the crystals by vaccum filtration. Finally
56
TLC studies

2: co-spot (1& 1d)
3: product (1d)
1 2 3 Rf values
591
Preparation of (1e,3e,6e,8e)-1,9-diphenylnona-1,3,6,8-tetraen-5-one
Reaction
O O
O 0
H 20 c
1H C
3 CH3 +2 NaOH
+
Ethanol mixture
propan-2-one 3-phenylpropanal (1E,3E,6E,8E)-1,9-diphenylnona-1,3,6,8-tetraen-5-one

M. F - C3H6O M.F - C9H10O M.F - C21H18O
M.W -58 M.W - 132 M.W - 286
Procedure
Prepare an ice - water bath in a 250ml beaker, place 15ml of ethanol and 20ml of aqueous 10%
Prepare the mixture of 1.5ml (2 mmol) of fresh Cinnamaldehyde and 758 µl (1 m mol) of Acetone
in a test tube over a period of 5-10mins, add the Cinnamaldehyde –acetone mixture to the ethanol-
NaOHsolution in a small portions, then stir the reaction for another 30 mins. Cool the mixture using
the ice water bath for one hour. Collect the crystals by vaccum filtration. Wash the crystals by
suspending them in 50ml of distil water. Again collect the crystals by vaccum filtration. Finally
56
TLC studies

2: co-spot (1& 1e)
3: product (1e)
1 2 3 Rf values
Percentage yield : 60.7%
592
Preparation of (2e, 6e)-2,6-dibenzylidenecyclohexanone

Reaction
O CHO O
200c
1 + 2
cyclohexanone benzaldehyde (2E,6E)-2,6-dibenzylidenecyclohexanone

M. F - C6H10O M.F - C7H6O M.F - C20H18O
M.W - 98 M.W - 106. M.W - 274
Procedure
reaches to 20°c, remove the ice-water bath, continue to stir the solute.
Prepare the mixture of 2.1 ml (2 m mol) of fresh Benzaldehyde and 1263.3µl (1 m mol) of
Cyclohexanone in a test tube over a period of 5-10 mins, add the Benzaldehyde-Cyclohexanone
mixture to the ethanol-NaOH solution in a small portions, then stir the reaction for another 30 mins.
Cool the mixture using the ice water bath for one hour. Collect the crystals by vaccum filtration. Wash
the crystals by suspending them in 50ml of distil water. Again collect the crystals by vaccum filtration.
56
TLC studies

2: co-spot (2& 2a)
3: product (2a)
1 2 3 R f values
Mobile phase: Benzene : Methanol (8:2)
R f value of the product : 0.92
593
Preparation of (2e,6e)-2,6(4-chlorobenzylidene)cyclohexanone
Reaction
O
O CHO
200c
1 + 2
NaOH-Ethanol mixture Cl Cl
Cl
cyclohexanone 4-chlorobenzaldehyde (2E,6E)-2,6-bis(4-chlorobenzylidene)cyclohexanone
M. F - C6H10O M.F - C5H3ClO M.F - C20H16Cl2O

M.W - 98 M.W - 140 M.W - 343
Procedure
Prepare the mixture of 2.8 ml (2 m mol) of fresh 4-Chloro benzaldehyde and 1263.3µl (1 m mol) of
Cyclohexanone in a test tube over a period of 5-10 mins, add the 4-Chloro benzaldehyde-
Cyclohexanone mixture to the ethanol-NaOH solution in a small portions, then stir the reaction for
another 30 mins. Cool the mixture using the ice water bath for one hour. Collect the crystals by
vaccum filtration. Wash the crystals by suspending them in 50ml of distil water. Again collect the
crystals by vaccum filtration. Finally recrystalised with ethyl acetate.
56
TLC plates

2: co-spot (2& 2b)
3: product (2b)
1 2 3 R f values
Percentage yield : 70.1%
594
Preparation of (2e, 6e)-, 2, 6 bis (4-nitrobenzylidene)cyclohexanone:

Reaction
O
O CHO
200c
1 + 2 NaOH-Ethanol mixture
O 2N NO 2
NO 2
cyclohexanone 4-nitrobenzaldehyde (2E,6E)-2,6-bis(4-nitrobenzylidene)cyclohexanone
M. F - C6H10O M.F - C6H4NO2 M.F - C20H16N2O5

M.W - 98 M.W - 151 M.W - 364.
Procedure
Prepare the mixture of 2.1 ml (2 mmol) of fresh 4-Nitro benzaldehyde and 1263.3µl (1 mmol) of
Cyclohexanone in a test tube over a period of 5-10 mins, add the 4-Nitro benzaldehyde-
another 30 mins. Cool the mixture using the ice water bath over night, collect the crystals by vaccum
filtration. Wash the crystals by suspending them in 50ml of distil water. Again collect the crystals by
vaccum filtration. Finally recrystalised with ethyl acetate.
56
TLC plates

2: co-spot (2& 2c)
3: product (2c)
1 2 3 R f values
595
Preparation of(2e, 6e)-2, 6-bis(4methoxybenzylidene)cyclohexanone

Reaction
O CHO O
200c
1 + 2
H3CO OCH3
OCH3
cyclohexanone 4-methoxybenzaldehyde (2E,6E)-2,6-bis(4-methoxybenzylidene)cyclohexanone
M. F - C6H10O M.F - C8H8O2 M.F - C22H22O3
M.W - 98 M.W - 136 M.W - 334
Procedure
Prepare an ice-water bath in a 250ml beaker, place 15ml of ethanol and 20ml of aqueous 10% NaOH
into a 100 ml beaker & add a stirbar. Place the 100ml beaker into the ice-water bath. Set then the
entire assembly on to a magnetic stirrer. While stirring, cool the solution to 20°c. After the solution
Prepare the mixture of 2.8 ml (2 m mol) of fresh 4-Methoxy benzaldehyde and 1263.3µl (1 m mol) of
Cyclohexanone in a test tube over a period of 5-10 mins, add the 4-Methoxy benzaldehyde-
another 30 mins. Cool the mixture using the ice water bath over night. Collect the crystals by vacuum
filtration. Wash the crystals by suspending them in 50ml of distil water. Again collect the crystals by
vacuum filtration. Finally recrystalised with ethyl acetate.
blue, wash the crystals again until red-litmus does not changes color. Keep a small sample aside to
56
TLC plates

2: co-spot (2& 2d)
3: product (2d)
1 2 3 R f values
596
Preparation of 1, 1'-[cyclohexane-1, 3-diylidenedi(1e,3e)prop-1-en-1-yl-3-ylidene]dibenzene :

Reaction
O O
O
0
20 c
H
1 + 2
cyclohexanone 3-phenylpropanal (2E,6E)-2,6-bis[(2E)-3-phenylprop-2-en-1-ylidene]cyclohexanone
M.F - C6H10O M.F - C9H10O M.F - C24H22O

M.W- 98 M.W -121 M.W - 326
Procedure
the entire assembly on to a magnetic stirrer. while stirring, cool the solution to 20°c. After the solution
Prepare the mixture of 2.1 ml (2 m mol) of fresh Cinnamaldehyde and 1263.3µl (1 m mol) of
Cyclohexanone in a test tube over a period of 5-10 mins, add the cinnamaldehyde-Cyclohexanone
mixture to the ethanol-NaOH solution in a small portions, then stir the reaction for another 30 mins.
Cool the mixture using the ice water bath for one hour. Collect the crystals by vaccum filtration. Wash
the crystals by suspending them in 50ml of distil water. Again collect the crystals by vaccum filtration.
56
TLC plates

2: co-spot (2& 2e)
3: product (2e)
1 2 3 R f values
Rfvalue of the starting material: 0.91
Percentage yield :64.1%
Antimicrobial Assay
Apparatus and Microorganism
The list of apparatus which were used in the antibacterial assay, were as follows: incubation bottle
(500 mL), sample bottles, tips and micropipette (10 µL and 500 µL), Whatman paper disc (6 mm),
disposable petri dishes (8 mm), disposable micro-titer well U shape, needles, glass rod, cotton and
test tubes (13 mm diameter,140 mm length). The apparatus were sterilized by autoclave for 15
minutes at 121ᵒC. Two bacteria namely Escherichia coli, Staphylococcus aureus and aeruginosa
were used in the antibacterial assay.
597
Preparation of Nutrient Agar and Broth

Antimicrobial assay was performed using nutrient agar and nutrient broth for bacteria. Nutrient agar
(28g) and nutrient broth (30g) each was suspended in one liter of distilled water. All solutions were
0
sterilized by autoclave for 15 minutes at 121 c.each compound (1mg) was dissololved in DMSO (1ml).
Culturing Microbe
Each of the selected microbes was impregnated in nutrient broth (20 ml) insterilized conical flask (250
0
ml). The flasks were sealed and kept in an incubator for24 hours at 37±1 c.
Preparation of Agar Plate

Sterilized agar (17 mL) was pipetted into petri dishes immediately. The agar was let to cool before the
dishes were kept in a refrigerator. The petri dishes were kept upside down in the refrigerator.
Disc Diffusion Method

The disc diffusion method was carried out on the cultures of microbes. The discs were prepared by
impregnating them in DMSO solution of each sample. The paper disc containing 1 mg of compound
was placed on the agar surface previously inoculated with suspension of each microbe to be tested.
All determinations were made in duplicate. Streptomycin sulphate (30 µg/disc) was used as the
positive control. Inhibition diameter was determined after incubation at 37oC ± 1 for 24hours. The
53
antimicrobial activity was indicated by the presence of clear inhibition zones around each disc .
4. TOTAL ANTIOXIDANT ACTIVITY

The total antioxidant activity was eluted using the method described by Prieto et al (1999).Ascorbic
acid was used as the standard antioxidant drug. 3ml of the extract/standard drug (0.1, 0.3,1 and 3
mg/ml) was placed in a test tube. 0.3 ml of reagent solution (0.6M sulphuricAcid, 28mM Sodium
Phosphate, 4Mm Ammonium molybdate) was then added and the resulting mixture was incubated at
0
95 C for 90 min. After the mixture has cooled to room temperature, the absorbance of the each
solution was measured using UV-Visible spectrophotometer at 695nm against blank.
The total antioxidant capacity was expressed as ascorbic acid equivalent using the Graph pad for
Window version 4.02 (Graph pad software, aSanDiego, CA,USA).
598
5. RESULTS
Physical results
Table 1:
1, 5-diphenylpenta-1,4-diyn -3-one
O
(1E, 4E)-1,5-diphenylpenta-1,4-dien-3-one
(1a)
S.No Compound 1(a) Results

1 Molecular formula C17H14O
2 Molecular weight 234
3 Percentage yield 82%
4 R f value 0.91
5 Melting point 1100c
Reported
6 1100c
melting point
Table 2:
(1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one
O
Cl Cl
(1E,4E)-1,5-bis(4-chlorophenyl)penta-1,4-dien-3-one
1(b)
S.No Compound 1(b) Results

1 Molecular formula C17H12Cl2O
4 R f value 0.92
0
5 Melting point 130-131 c
Reported melting 0
6 131-132 c
point
599
Table 3:
(1E, 4E)-1,5-bis(4-nitrophenyl)penta-1,4-dien-3-one
O 2N NO 2
(1E, 4E)-1, 5-BIS (4-NITROPHENYL)PENTA-1,4-DIEN-3-ONE
1(c)
S.No Compound 1(c) Results

1 Molecular formula C17H12N2O5
4 R f value 0.94
5 Melting point 147-1480c
Reported
6 1470c
melting point
Table 4:
(1E, 4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one
O
H3CO OCH3
(1E, 4E)-1,5-BIS(4-METHOXYPHENYL)PENTA-1,4-DIEN-3-ONE :
1(d)
S.No Compound 1(d) Results
1 Molecular formula C19H18O3

4 R f value 0.92
Reported
6 187-1880c
melting point
600
Table 5:
(1E,3E,6E,8E)-1,9-diphenylnona-1,3,6,8-tetraen-5-one :
O
(1E,3E,6E,8E)-1,9-diphenylnona-1,3,6,8-tetraen-5-one
1(e)
S.No Compound 1(e) Results
3 Percentage yield 60.7%
4 R f value 0.93
6 Reported melting point 1720c
Table 6:
(2E,6E)-2,6-DIBENZYLIDENECYCLOHEXANONE
O
(2E,6E)-2,6-dibenzylidenecyclohexanone
2(a)
S.No Compound 2(a) Results
4 R f value 0.92
6 Reported 1170c
melting point
Table 7:
(2E, 6E)-, 2, 6-bis(4-chlorobenzylidene)cyclohexanone
O
Cl Cl
2(b)
S.No Compound 2(b) Results

1 Molecular formula C20H16Cl2O
4 R f value 0.94
5 Melting point 1460c
Reported
6 147-1480c
melting point
601
Table 8:
(2E,6E)-2,6-BIS(4-NITROBENZYLIDENE)CYCLOHEXANONE
O
O 2N NO 2
(2E,6E)-2,6-bis(4-nitrobenzylidene)cyclohexanone
2(c)
S.No Compound 2(c) Results
1 Molecular formula C20H16N2O5
4 R f value 0.96
Reported
1590c
6 melting point
Table 9:
(2E,6E)-2,6-BIS(4-METHOXYBENZYLIDENE)CYCLOHEXANONE
O
H3CO OCH3
(2E,6E)-2,6-bis(4-methoxybenzylidene)cyclohexanone
2(d)
S.No Compound 2(d) Results

1 Molecular formula C22H22O3
4 R f value 0.93
Reported
6 203-2040c
melting point
Table 10:
(2E,6E)-2,6-BIS[(2E)-3-PHENYLPROP-2-EN-1-YLIDENE]CYCLOHEXANONE
O
(2E,6E)-2,6-bis[(2E)-3-phenylprop-2-en-1-ylidene]
Cyclohexanone 2(e)
S.No Compound 2(e) Results
4 R f value 0.95
6 Reported 1800c
melting point
602
ACTIVITY RESULTS
Mean zone of inhibition(mm/mg)
Staphylococcus Echerichia coli
Aureus
S.NO
sample 50 100 150 200 50 100 150 200
µg µg µg µg µg µg µg µg
1 Control(DMF) - - - - - - - -
2 Benzyl penicillin 19 23 27 32 - - - -
3 streptomycin - - - - 20 24 29 34
4 1a - - - - - - - -
5 1b - - - - - - - -
6 1c - - - - - - - -
7 1d - - - - - - - -
8 1e - - - - - - - -
9 2a - - - - - - - -
1o 2b - - - - - - - -
11 2c - - - - - - - -
12 2d - - - - - - - -
13 2e - - - - - - - -
ANTI-OXIDANT ACTIVITY RESULTS

COMPOUND (1a)
Table 1:
ABSORBANCE OF ABSORBANCE OF ASCORBIC
CONCENTRATIONS
COMPOUND (1a) ACID(POSITIVE CONTROL)
100 µgm/ml 0.025333±0.004509 0.258233±0.001305
200 µgm/ml 0.046±0.0004583 0.3042±0.000755
300 µgm/ml 0.09167±0.007638 0.3324±0.001015
400 µgm/ml 0.145331±0.005033 0.433567±0.00095
500 µgm/ml 0.257667±0.003512 0.7322±0.0007552
Solubility: Methanol
Graph.1:
COMPOUND (2a)
Table 1:
ABSORBANCE OF
ABSORBANCE OF ASCORBIC
CONCENTRATIONS COMPOUND (1a) ACID(POSITIVE
CONTROL)
100 µgm/ml 0.01±0.000954 0.258233±0.001305
200 µgm/ml 0.012433±0.000551 0.3042±0.000755
300 µgm/ml 0.036433±0.000603 0.3324±0.001015
400 µgm/ml 0.059733±0.000643 0.433567±0.00095
500 µgm/ml 0.0985±0.0005 0.7322±0.0007552
603
Graph. 2:
COMPOUND (2d)
Table 1:
ABSORBANCE OF
CONTROL)
100 µgm/ml 0.008433±0.000551 0.258233±0.001305
200 µgm/ml 0.010333±0.001172 0.3042±0.000755
300 µgm/ml 0.023733±0.000404 0.3324±0.001015
400 µgm/ml 0.32433±0.000666 0.433567±0.00095
500 µgm/ml 0.02633 ±0.000471 0.7322±0.0007552
Graph.3:
COMPOUND (2e)
Table 1:
ABSORBANCE OF
CONTROL)
100 µgm/ml 0.013267±0.000702 0.258233±0.001305
200 µgm/ml 0.029833±0.001021 0.3042±0.000755
300 µgm/ml 0.045267±0.003591 0.3324±0.001015
400 µgm/ml 0.118433±0.001504 0.433567±0.00095
500 µgm/ml 0.21467±0.005686 0.7322±0.0007552
604
Graph. 4:
6. SUMMARY AND CONCLUSION

1. Ketones (Acetone, Cyclohexanone) were treated with different aldehydes(4-Chloro
benzaldehyde, 4-nitrobenzaldehyde, 4-methoxybenzaldehyde, cinnamaldehyde) by aldol
condensation to give the corresponding ‘’dibenzal ketone derivatives’’ (1a-1e, 2a-2e),title
compounds in good yield.
2. All the compounds synthesized were characterized by physical (R f values, M.P.,
Molecular weight, molecular formula).
3. The title compounds were screened for antibacterial and anti-oxidant activity. According
to the results obtained, it can be concluded that none of the synthesized compounds
have antibacterial activity.
4. As for the ant-oxidant activity, (2a), (2e),compounds showed better activity.
5. Further lead optimization should be carried out for the better expected anti-oxidant
activity.
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IJRPC 2017, 7(4), 585-606 Kundavaram Raju et al ISSN: 22312781

INTERNATIONAL JOURNAL OF RESEARCH IN PHARMACY AND CHEMISTRY

Available online at www.ijrpc.com Research Article

SYNTHESIS AND ANTI-OXIDANT

200c NaOH-Ethanol mixture

propan-2-one benzaldehyde (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one

1: starting material (1)

M. F - C3H6O M.F -C5H3ClO M.F - C17H12Cl2O

1: starting material (1)

Preparation of (1e, 4e)-1,5-bis(4-nitrophenyl)penta-1,4-dien-3-one:

propan-2-one 4-nitrobenzaldehyde (1E,4E)-1,5-bis(4-nitrophenyl)penta-1,4-dien-3-one

M. F - C3H6O M.F - C6H4NO2 M.F - C17H12N2O5

1: starting material (1)

Preparation of (1e, 4e)-1, 5-bis(4-methoxyphenyl)penta-1,4-dien-3-one:

propan-2-one 4-methoxybenzaldehyde (1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-one

1: starting material (1)

propan-2-one 3-phenylpropanal (1E,3E,6E,8E)-1,9-diphenylnona-1,3,6,8-tetraen-5-one

1: starting material (1)

Preparation of (2e, 6e)-2,6-dibenzylidenecyclohexanone

cyclohexanone benzaldehyde (2E,6E)-2,6-dibenzylidenecyclohexanone

1: starting material (2)

M. F - C6H10O M.F - C5H3ClO M.F - C20H16Cl2O

1: starting material (2)

Preparation of (2e, 6e)-, 2, 6 bis (4-nitrobenzylidene)cyclohexanone:

cyclohexanone 4-nitrobenzaldehyde (2E,6E)-2,6-bis(4-nitrobenzylidene)cyclohexanone

M. F - C6H10O M.F - C6H4NO2 M.F - C20H16N2O5

1: starting material (2)

Preparation of(2e, 6e)-2, 6-bis(4methoxybenzylidene)cyclohexanone

1: starting material (2)

Preparation of 1, 1'-[cyclohexane-1, 3-diylidenedi(1e,3e)prop-1-en-1-yl-3-ylidene]dibenzene :

cyclohexanone 3-phenylpropanal (2E,6E)-2,6-bis[(2E)-3-phenylprop-2-en-1-ylidene]cyclohexanone

M.F - C6H10O M.F - C9H10O M.F - C24H22O

1: starting material (2)

Preparation of Nutrient Agar and Broth

Preparation of Agar Plate

Disc Diffusion Method

4. TOTAL ANTIOXIDANT ACTIVITY

S.No Compound 1(a) Results

S.No Compound 1(b) Results

S.No Compound 1(c) Results

1 Molecular formula C19H18O3

S.No Compound 2(b) Results

S.No Compound 2(d) Results

ANTI-OXIDANT ACTIVITY RESULTS

6. SUMMARY AND CONCLUSION

21. Zheng M, Wang L, Shao J and Zhong Q. Synth Commun. 1997;27:351.

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