WELCOME

MICROWAVE INDUCED SYNTHESIS,

CHARACTERIZATION AND
PHARMACOLOGICAL STUDIES OF
COPPER (II), NICKEL (II) AND ZINC
(II) COMPLEXES DERIVED FROM
CURCUMINO – 4
AMINOANTIPYRINE AND
ANTHRANILIC ACID

BY
V. VEERARAJASUNDARI,
M.PRATHEEPHA,
(M.Sc. CHEMISTRY)
Introduction
 Schiff base of curcumino- 4-aminoantipyrine and its metal
complexes have a variety of applications in biological, clinical,
analytical and pharmacological areas. It has been improved by
condensing it with aldehydes , amines and amino acids
 Tetra dentate Schiff bases composed of Anthranilic acid donor
atoms are very important chelating ligands for designing
medicinally and catalytically useful metal complexes.
 Amino acids play an important role in many physiological
activities of the human body and also helpful in understanding
biological functions of macromolecules such as proteins.
 In particular histidine, tryptophan amino acids analogues are
useful in antimicrobial therapeutics
Objectives of the Present
Work
To synthesize variety of Schiff base using
curcumino- 4-amino antipyrine, aldehyde, ketone and
aminoacid containing additional functional groups.
To characterize each compound by using several
physico-chemical and various spectroscopic methods.
The synthesized compounds are utilised to test against
various microorganism growth.
Experimental Methods and
Physical Techniques
 Elemental Analysis
 UV-Visible spectra
 IR Spectra
 NMR Spectra
 Molar conductance
 Microbial Activity
 Analgesic Activity
 OMe OMe
NH Me
OH OH 2

+ Me N
N O

O Ph
O
4-amino antipyrine
Curcumin

Heating
for 10 mins

OMe OMe

OH OH

Me N OH

Me N
N O
Ph

Curcuminyl 4-amino antipyrine

 OMe OMe

OH OH
NH2
COOH
+
Me N OH

Me N Anthranilic acid
N O
Ph
Curcuminyl 4-amino antipyrine

Heating
H2O
for 6 mins

OMe OMe

OH OH

Me N OH

COOH
Me N
N N
Ph

Schiff base
 OMe OMe

OH OH

Me N OH
MCl2
COOH
Me N
N N
Ph

Schif f base
Heating
for 12 mins

OMe OMe

OH OH

N O

Me M O

C O
Me N
N N

Ph
Metal Complex M = Cu (II ), Ni(I I), Zn(I I)
RESULT AND DISCUSSION
 The schiff base of subjected to elemantal analysis. The
result of elemantal analysis with molecular formula and the
melting point, molar conductance, magnetic studies are
present in the following table.

 Cu (II), Ni (II), and Zn(II) complexes are amorphous

powder, insoluble in water and ether. Completely soluble
in solvents such as Dimethylsulphoxide and acetonitrile.

 Schiff base ligand and complexes are generally

characterized by a variety of techniques, such as eletronic
spectra, infrared spectra and 1H – NMR spectra has been
used in this works are presented.
Physical characterization, analytical, molar conductance and magnetic susceptibility data of
the Schiff bases and their complexes

Found
Compou Molecular Formu Colour Yield Melti (caled) µeff AM ×
nd Formula -la (%) -ng (%) (Bm) 10-2
Weight Point M C H N O (mho
cm2
mol-1)
HL C32H31N3O6 553.6 Red 84.6 83 - 69. 5.6 7.5 17. -
3 34
H2L C39H36N4O7 672.72 Reddis 91.4 130 - 69. 5.3 8.3 16. -
h 6 9 6
brown
[NiL] [Ni C39H34N4O7] 734.25 Brown 90.6 Abov 8.0 64. 4.7 7.6 15.
e 300 5 7 35 2.96 0.174
[CuL] [Cu 729.40 Black 87 280 8.6 63. 4.6 7.6 15.
C39H34N4O7] 5 7 7 25 1.76 0.168
[ZnL] [Zn C39H34N4O7] 736.09 Brown 83 220 8.8 63. 4.6 7.6 15. -
8 6 6 21 0.132
 Electronic absorption spectral data
of the Schiff base and copper
complex
SL.NO COMPOUND ABSORPTI- BAND GEOMETRY
ON ASSIGNMENT

1. H2C4AAPAA 353, 275 INCT -

2. [Cu(C4AAPAA)] 575, 545 2B

1g  2B2g Square planar
UV SPECTRUM OF SCHIFF BASE
AND COPPER COMPLEX
IR SPECTRA OF SCHIFF BASE AND ITS
Cu (II) AND Ni (II) COMPLEXES
Metal Complexes

Functional group Schiff Base

Cu Ni complex
complex
COOH group of Strong broad band at Disappeare Disappeare
Anthranilic acid and 2360 cm-1 and d d
Enolic OH group 3402 cm-1
-C=N 1652 cm-1 1605 cm-1 1614 cm-1

-C=O 1629 cm-1 1553 cm-1 1593 cm-1

M-O - 510 cm-1 502 cm-1

M-N - 495 cm-1 450cm-1

IR SPECTRA FOR SCHIFF BASE AND
Cu, Ni METAL COMPLEXES
PROTON NMR FOR SCHIFF BASE
AND ZINC COMPLEX
ANALGESIC ACTIVITY
Basal reaction time after drug
Sl. No Drug and dosage Body weight administration (sec)

1hr 2hr 3hr 4hr

H- 130 2 1 1 1
1 Control B- 120 3 2 1 2
T- 130 2 3 2 1
C- 130 1 2 3 3
Standard H- 120 6 8 4 7
2 Diclofenac sodium 10mg/kg B- 140 5 7 5 5
T- 130 5 6 7 6
C- 150 4 5 8 7
H- 130 3 5 4 5
3 Schiff base B- 120 3 4 6 7
400mg/kg T- 150 2 4 5 6
p.o. C- 140 3 3 4 5
CNS DEPRESSANT ACTIVITY
Drug Dose Before After % Change in
Treatment (mg/kg) Treatment Treatment activity
Caffeine 30 mg/kg 58 ± 2.9439 96 ± 2.1602 65.85
(i.p)
Chlorpromaz 3mg/kg (i.p) 57.25 ± 3.8622 23.25 ± 3.4034 59.33
ine
H2C4AAPA 400 mg/kg 55.25 ± 3.5118 26 ± 3.1622 53.23
(p.o)
ANTIMICROBIAL ACTIVITY FOR
SCHIFF BASE
 Organisms Concentration of extract & zone of inhibition (mm)

SB 1 100 µl SB 2 100 µl

Klebisella SP 8 19

Pseudomonas SP 4 21

Condida SP 7 23

Achremonium SP - 18
 CONCLUSION
 Neutral complexes of Cu(II), Ni(II) and Zn(II) have been
also synthesized from the Schiff bases derived from
Curcumino- 4-amino antipyrine and Anthranilic acid.
 All the complexes were characterized by spectral and
analytical data .
 From the spectral and stoichiometric analysis, a square-
planar geometry was assigned for the monomeric metal
complexes.
 The antimicrobial activity of the ligand and its complexes
confirmed, all the metal chelates have higher antimicrobial
activity than the free ligand.