The document summarizes the synthesis and characterization of novel Cinnoline derivatives. Several students synthesized Cinnoline derivatives using Aniline as the starting material. The compounds were characterized using melting point, TLC, molecular formula determination, NMR and thin layer chromatography. The %yield of the compounds ranged from 82-93%. The compounds were further evaluated for their in-vitro antioxidant and antimicrobial activity. Pharmacological screening showed potential for treatment of fungal diseases.

1. k.Tharangini k.Priyanka v.Hareeshkumar
(16Q01R0091) (16Q01R0059) (16Q01R0022)
S.Varunkumar J.Manjula M.Sunanda
(16Q01R0093) (16Q01R0040) (16Q01R0084)
M.Chandrasekhar M.Madhu sudhana
(16Q01R0014) (16Q01R0037)
Under the guidance of
DR.P.R.Logesh
kumar,M.pharm,Ph.D..,
Associate Professor
Department of pharmaceutical chemistry.
SRI KRISHNA CHAITHANYA
COLLEGE OF
PHARMACY,MADANAPALLE.
Synthesis Experiments and pharmacological
screening of some novel Cinnoline derivatives
Presented by

2. Cinnoline is also known as 1,2-diazanaphthalene or
benzo-1,2-diazene
Cinnoline itself is toxic.The starting compound of
cinnoline is Anilineand Sodium nitrite.
It is a pale yellow solid of geranium like odour.
NUCLEUS INTRODUCTION
CINNOLINE
other name:Benzopyridazine
Molecular formula C8H6N2
Molecular weight 130gm
Melting point 38oC
Boiling point 0.351140mmHg
Solubility Ethanol,Methanol,DMSO,DM
F

3. Aniline and its ring-substituted derivatives react with
nitrousacid to form diazonium salts
Its main use in the manufacture of precursors to polyurethane and other
industrial chemicals.
IN this reaction primary aromatic amine reacts with sodium nitrite and
with 2mloes of HCL as major product and water and sodium chloride.
INTRODUCTION TO STARTING MATERIAL
ANILINE
Other names:Phenylamine,Aminobenzene,Benzamine
Molecular formula C6H7N
Molecular weight 93.129gm
Melting point -6.3oC
Boiling point 184.13oC

4. S . Hurmath Unnisa* Et.al , Synthesis and screening of pyrazole based
cinnoline derivatives for its anti tubercular and anti fungal activity was
synthesized .
Sony . S* Et.al , A concise review on cinnoline and its biological
activities .
LITERATURE REVIEW

5. Literature servey reveals that,the derivatives of Cinnoline have high
potential biological activity,processing a wide range of anti fungal
activity.Biological derivatives Cinnoline like anti-inflammatory,anti-
bacterial,anti-fungal.
Collected literature from various journals Synthesized of Cinnoline
derivatives
1) Melting point
2) Boiling point
3) Solubility
Characterised the synthesis compounds of spectral methods.
Evaluated the biological activity of newly synthesized compounds
PLAN OF WORK

6. STEP-1:
1-chloro-2-phenyl diazene is prepare by dissolving sodium nitrite(0.1 mole)
in 26ml of water and added drop wise to a solution of amine(10ml in 1N
HCL) at 0oc under stirring for about 30mins and reflux for 1hr.
Then orange coloured precipitate is collect by filtration and dried.
Ethanol,1Hr
STEP-2:
To a solution of compound(0.2 mole) in ethanol,pentane 2,4dione(0.2 mole)
is added.
The mixture is refluxed for 5 hours.
The solvent is evaporated and the solid obtained is recrystalized from
petroleum ether.
Ethanol,pentane-2,4-dione
EXPERIMENTAL WORK

7. STEP-3:
Compound 2 (0.1 mole) in ethanol (10ml),20ml of poly phosphoric acid is
added.
The mixture is maintained under reflux for 6 hours.
After cooling,the mixture is poured on ice and the solid formed is collected by
filtration,washed with cold water and recrystalized from ethanol.
Polyphosphoric acid,6H
STEP-4:
Compound 3(0.1 mole) in 30ml of ethanol and 30ml of formaldehyde.
The mixture is maintained under reflux for 6 hours.
The solvent is evaporated and the solid obtained is recrystalized from
petroleum ether.
Ethanol,formaldehyde,6H

8. MATERIALS AND INSTRUMENTS
 INSTRUMENTS
 VEEGO Digital melting point
apparatus.
 Perkin elmer spectrum
version 10.03.07.IR
spectrometer
 JEOL GC mate mass
spectrometer
 UV spectroscopy
 Hot air oven,Thermometer
 Single pan electronic
balance
 Heating mantle,Incubator
 Ultra sonicator
 CHEMICALS
 Aniline
 Sodium nitrite
 Ethanol
 Pentane-2,4-dione
 Poly phosphoric acid
 Formaldehyde
 Sodium nitropruside
 Phosphate buffer
 Griess reagent

9. Melting point and appearance
PHYSICAL CHARACTERISATION
S.NO Compoun
d code
Melting
point
Appearan
ce
% of yield
1 compoun
d1
80 0c Pure
white
93%
2 compoun
d2
76 0c White 86%
3 compoun
d3
77 0c White 84%
4 compoun
d4
82 0c white 82%
5 A1 140 0c Colourles
s solid
powder
90%
6 A2 138 0c White
crystals
88%
7 A3 153 0c Colourles
s or white
91%

11. The purity of all synthesized compounds was monitored on TLC
THIN LAYER CHROMATOGRAPHY
S.NO Compound code Rf value
1 compound1 0.51
2 compound2 0.14
3 compound3 0.83
4 compound4 0.82
5 A1 0.82
6 A2 0.68
7 A3 0.84

12. The molecular formula and molecular weight of all the synthesized
compounds are given
MOLECULAR FORMULA AND MOLECULAR WEIGHT
S.NO Compound
code
Molecular
formula
Molecular
weight(gm)
1 compound1 C6H5ClN2 146.5gm/mol
e
2 compound2 C11H12N2O
2
204gm/mole
3 compound3 C11H12N2O 188gm/mole
4 compound4 C13H17N2O 217gm/mole
5 A1 C7H6O2 122.12gm/m
ole
6 A2 C7H6O3 138.12gm/m
ole
7 A3 C6H8O7 192.12gm/m
ole

13. INTRODUCTION
NMR spectroscopy is powerful analytical technique used to charaterised
organic molecules by identified carbon-hydrogen frame works with in molecules
To common types of NMR spectroscopy are used to charaterised organic
structure 1 H NMR is used to determine the type and number of H atoms in a
molecule 13C NMR is used to determine the type of carbon atoms in the
molecule
Source of energy in NMR is radio waves which have long wavelength and thus
low energy and frequency
When low energy radio waves interact with a molecule, they can change the
nuclear spins of some elements including 1H and13C.
PRINCIPLE OF NMR SPECTROSCOPY
Nuclei of all elements carry a charge. When the spins of the protons and
neutrons comprising these nuclei are not paired, the overall spin of the charged
nucleus generates a magnetic dipole along the spin axis, and the intrinsic
magnitude of this dipole is a fundamental nuclear property called the nuclear
magnetic moment, µ. The symmetry of the charge distribution in the nucleus is
a function of its internal structure and if this is spherical (ie analogous to the
symmetry of a 1s hydrogen orbital), it is said to have a corresponding spin
angular momentum number of I=1/2, of which examples
are 1H, 13C, 15N, 19F, 31P etc. Nuclei which have a non-spherical charge
STRUCTURAL CONFIRMATION

14. USES OF NMR SPECTROSCOPY
NMR used in biology to study the biofluids,cell,perfused organs and
biomacromolecules such as nucleic acid (DNA , RNA) carbohydrates ,
proteins and peptides . And also labeling studies in laboratory.
NMR is used in physics and chemistry to study high pressure diffusion ,liquid
crystals ,liquid crystals solution ,membrane ,rigid solids.
NMR is used in food science.
APPLICATIONS OF NMR
NMR spectroscopy is a non destructive analytical technique that is used to
probe the nature and characteristic of molecular structure .A simple NMR
experiment produces information in the form of a spectrum ,which is able to
provide details about;
The type of atoms present in the sample
The relative amount of atoms present in a sample
The specific environments of atoms with in a molecule
The purity and composition of a sample
Structure information about a molecule ,including constructional and
conformational isomerisation.

15. INTRODUCTION
Chromatographic theory describes the physicochemical relationships
governing separations.
Usually, semiempirical models of the chromatographic process that have a
relatively simple thermodynamic background and give a bulk picture of the
physical or chemical phenomena are involved. Macroscopic models of the
chromatographic process cannot mirror the respective separation
mechanisms in any other way. Exceptions to this rule, if any exist, are rather
negligible. It is important to keep in mind two facts. First, one always has to
be aware of the complexity of chromatographic processes, and consequently
of limitations of the existing semiempirical models.
BASIC PRINCIPLE
chromatography works on the principle that different compounds will have
different solubilities and adsorption to the two phases between which they
are to be partitioned. Thin Layer Chromatography (TLC) is a solid-liquid
technique in which the two phases are a solid (stationary phase) and a liquid
(moving phase
THIN LAYER CHROMATOGRAPHY

16. PROCEDURE
With a pencil, a thin mark is made at the bottom of the plate to apply the sample
spots.
Then, samples solutions are applied on the spots marked on the line in equal
distances.
The mobile phase is poured into the TLC chamber to a leveled few centimeters
above the chamber bottom. A moistened filter paper in the mobile phase is placed
on the inner wall of the chamber to maintain equal humidity (and also thereby
avoids edge effect this way).
Now, the plate prepared with sample spotting is placed in the TLC chamber so
that the side of the plate with the sample line is facing the mobile phase. Then the
chamber is closed with a lid.
The plate is then immersed, such that the sample spots are well above the level of
mobile phase (but not immersed in the solvent — as shown in the picture) for
development.
Applications
To check the purity of the given samples.
Identification of compounds like acids, alcohols, proteins, alkaloids, amines,
antibiotics, and more.

23. In-vitro antioxidantactivity :
All the compounds were subjected to in-vitro antioxidant
RESULTS AND DISCUSSION

27. Pharmacology
pharmacology is a separate discipline in the health
sciences. Pharmacology is the study of how a drug affects a
biological system and how the body responds to the drug.
The discipline encompasses the sources, chemical properties,
biological effects and therapeutic uses of drugs.
Pharmacology has two major branches:
Pharmacokinetics, which refers to the absorption,
distribution, metabolism, and excretion of drugs.
Pharmacodynamics, which refers to the molecular,
biochemical, and physiological effects of drugs, including
drug mechanism of action.
PHARMACOLOGY

28. Chemotherapy of fungal diseases
CHEMOTHERAP
Y OF
FUNGAL
DISEASES

51. THANK
YOU

52. Presented By:
SEMINAR ON CHEMOTHERAPY OF
FUNGAL
M.Madhu sudhana(16Q01R0037)
4Th Year B.Pharmacy
Sri Krishna Chaithanya College Of Pharmacy
Madanapalle