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Introduction:.

 

 Jesus

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Introduction:

Pyrimidinones are
remarkable scaffolds having wide range of biological importance.
thiamine,uracil and  cytocine are
pyrimidine bases and they are found in DNA and RNA respectively which plays
vital role in biological  cell function .
In recent years dihydropyrimidinones received more attention because they
exhibit wide range of biological and therapeutic activities such as anti tumor,
anti viral, antimicrobial, anti-inflammatory activities1, potent
calcium channel modulators, anti hypertensive agents and neuropeptide Y (NPY)
antagonists 2.dihydropyrimidinone also found in many marine natural products including
Betzelladine is an alkaloid which process HIVgp-120-CD4 inhibiting
activity3.

Biginelli
reaction is the classical example for single pot multi-component reaction
involving cyclocondensation of an aldehyde, active methelene group containg
compounds (?-keto ester, acetyl acetone..,etc.). and urea in presence of acid4.

EXPERIMENTAL
PART:

MATERIALS AND
METHODS: All the chemicals used in the synthesis were procured from Sigma
Aldrich. TLC plates for monitoring of reactions and silica gel (100-200 mesh)
for column chromatography obtained from Merck. The Melting points were
determined by using EZ-Melt automated melting point apparatus.  The FT-IR spectra were recorded on BRUKER
ALPHA-T FT.IR spectrophotometer using KBr pellet method. The Mass spectra were
recorded on Agilent 6320 Ion Trap LC-MS (Positive/Negative ion electro spray
ionization method). The 1H NMR spectra of the compounds were recorded on BRUKER
400 MHz NMR Spectophotometer.

Step: 1 synthesis of Dihydro pyrimidinone
derivatives:

A mixture of Aldehyde(10mmol),
acetylacetone(11mmol),urea(13mmol) and citric acid (5mmol) were taken in a round
bottomed flask and refluxed for 6-12 hours at 800C. After completion
of reaction as monitored by TLC, obtained crude product was transferred into a  beaker containing crushed ice, filtered,
washed with ice cold water and recrysteallized using ethanol.

spectral data of synthesied compound

IR: 1688.73(C=O), 3333. 80(NH), 1124.11(OC2H5),
1607.42(C=C), 1240.38(C-N)

NMR: 1.34(3H,CH3); 2.06 (3H,CH3 S); 2.27 (3H,COCH3 S );
4.01(2H, OCH2);5.18 (1H, C-H); 6.83(1H Ar –H S);6.62(1H,Ar-H); 6.60(1H,
Ar-H);9.09(1H,CONH); 8.85 (1H,OH);7. 69 (1, NH)

 

Step:2 synthesis of chalcones of dihydro
pyrimidinones:

A mixture of
compound j(1mmol), aldehydes(1mmol) and ethanol(to soluble the contents) were
taken in a beaker and to that add 10 ml of 30% aqueous solution of NaOH and
then subjected to stirring up to 48 hours reaction was monitored by TLC. After
completion of the reaction, reaction mixture was poured on to ice cold water
and acidified with dil.HCl. Then obtained solid was filtered,washed with water
and obtained products were purified by column chromatography.

IR :1688.73(C=O), 3333. 80(NH), 1124.11(OC2H5),
1607.42(C=C), 1240.38(C-N)

NMR: 1.34(3H,CH3); 2.06 (3H,CH3 S); 2.27 (3H,COCH3 S );
4.01(2H, OCH2);5.18 (1H, C-H); 6.83(1H Ar –H S);6.62(1H,Ar-H); 6.60(1H,
Ar-H);9.09(1H,CONH); 8.85 (1H,OH);7. 69 (1, NH)

COMPOUND2

 

 

 

         S.no

stracture

IUPAC name

1

a

 

2

b

 

3

c

 

4

d

 

5

e

 

6

f

 

7

g

 

8

h

 

9

i

 

10

j

 

 

 

 

 

 

s.no

Compound   code

Structures

IUPAC name

11

2a

 
 

12

2b

 
 

13

2c

 
 
 

14

2d

 
 

15

2e

 
 
 

 

 

 

 

 

 

 

 

 

ANTIBACTERIAL
ACTIVITY

TEST
ORGANISM :

Gram
positive:Staphylococcus
aureus

Gram
negative:Escherichia
coli

Antimicrobial activity was determined by
using agar cup plate method.The tested organism were sub cultured on nutrient
agar medium for bacteria Ampicillin
was used as reference drug for bacterial strain.The medium used for the
antibacterial study has the following composition g/L:Peptone, ; Beef
extract, ; sodium chloride; and agar in distilled water  pH was adjusted at 7. Bacterial culture was
incubated at 37? C for 24 h.The solution of the test compounds were prepared by
dissolving 0.5mg/1ml and 1mg/10ml of dimethylsulfoxide at a concentration of
100µg/50µl and 250µg/50µl. The cups each of 10 in diameter were made by
scooping out medium with a sterilized cork borer in a Petri. The solutions of
each test compound (50 µL) were added separately in the cups and petri dishes
were subsequently incubated at 37 0C for 24 hours. Zone of inhibition produced
by each compound was measured in . Compounds were screened for their
antibacterial activity.

Test results:

S.NO

COMPOUNDS

                        Zone of
inhibition(mm)

Staphylococcus
aureus

Escherichia
coli

50µg/ml

100 µg/ml

50µg/ml

100µg/ml

1

1a

10

12

12

13

2

1b

10

13

10

3

1c

11

14

13

18

4

1d

13

15

11

15

5

1e

11

16

15

16

6

1f

11

13

11

14

7

1g

12

14

12

17

8

1h

13

17

15

17

9

1i

12

14

13

14

10

1j

11

13

10

12

       11

2a

14

16

15

16

12

2b

15

17

16

17

13

2c

15

18

16

19

14

2d

15

18

15

19

15

2e

14

17

14

17

16

Ampicillin

17

19

19

21

 

Results and discussions:

All the dihydropyrimidinonene derivatives
(1a-1j) and their chalcones(2a-2e)were evaluated for their antibacterial
against both gram positive (Staphylococcus areus) and gram negative (E.coli),
by using cup plate method. The results of antibacterial activity were given in
table no: interestingly all the synthesized dihydropyrimidinone derivatives
were shown mild to moderate antibacterial activity at 50µg/ml and 100µg/ml
concentration , when compared with the standard drug (Ampicillin) at same
concentrations . Compounds 1c, 1e, 1i, 2c and 2d were shown good antibacterial
activity against both gram positive and gram negative organisms.

 

ANTIFUNGAL ACTIVITY

Test  Organism:Aspergillus niger

Antifungal activity was determined by
using agar cup plate method. The tested organism Aspergillus niger was sub cultured on potato-dextrose agar (PAD) for fungi. Fluconazole was used as positive
control for fungi. Fungal culture was incubated at 25-30 0C for 4-5 days. .The
solution of the test compounds were prepared by dissolving /1ml and 5mg/1ml of
dimethylsulfoxide at a concentration of 50µg/1ml and 100µg/1ml. The cups each
of 10 in diameter were made by scooping out medium with a sterilized cork borer
in a Petri dish. The solutions of each test compound (50µL) were added
separately in the cups and petri dishes were subsequently incubated incubated
at 25-30 0C for 4-5 days.. Zone of inhibition produced by each compound was
measured in .Compounds was screened for their antifungal activity.

All the dihydropyrimidinonene
derivatives (1a-1j) and their chalcones(2a-2e)were evaluated for their
antibacterial against both gram positive (Staphylococcus areus) and gram
negative (E.coli), by using cup plate method. The results of antibacterial
activity were given in table no: interestingly all the synthesized
dihydropyrimidinone derivatives were shown mild to moderate antibacterial
activity at 50µg/ml and 100µg/ml concentration , when compared with the
standard drug (Ampicillin) at same concentrations . Compounds 1c, 1e, 1i, 2c
and 2d were shown good antibacterial activity against both gram positive and
gram negative organisms.

 

Results and discussions:

All the dihydropyrimidinonene
derivatives (1a-1j) and their chalcones(2a-2e)were evaluated for their
antifungal acticity against  Aspargillus
niger, by using cup plate method. The results of antifungal activity were given
in table no: it is noticed that all the synthesized dihydropyrimidinone
derivatives were shown mild to moderate antifungal activity at 50µg/ml and
100µg/ml concentration , when compared with the standard drug (Fluconazole) at
same concentrations . Compounds 1c, 1i,
2b and 2d were shown good
antifungal activity.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

S.NO

COMPOUNDS

Zone of inhibition(mm)

Asparagillus
niger

50 µg/ml

100 µg/ml

1

1a

13

15

2

1b

14

16

3

1c

16

20

4

1d

16

18

5

1e

14

16

6

1f

15

18

7

1g

15

17

8

1h

15

20

9

1i

15

16

10

1j

14

16

11

2a

17

19

12

2b

17

23

13

2c

16

20

14

2d

17

       22

15

2e

17

20

16

Fluconozole

22

25

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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