1. ST. XAVIERS COLLEGE
(AUTONOMOUS)
Name:- Sunny Patel (21-PCH-032)
 Aayush Patel (21-PCH-031)
Class:- M.Sc. (Organic Chemistry)
Semester:-III
Seminar Topic:- Synthesis ,Antioxidant and Antibacterial activities of Quinoline
incorporated 2,4,5-trisubstituted imidazole derivatives.

2.  Introduction:-
Quinoline:-
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N.It is a
colourless hygroscopic liquid with a strong odur.
It is slightly soluble cold water but dissolve readily in hot
water and most organic solvents.
The Quinoline is found in many naturally occupiying alkaloids.
Quinoline is an antimalerial drug and has been isolated from the bark of cinchona trees.
Many synthetic druges used for the treatment of malaria such as chloroquine,plasmoquin, atebrin
containing quinoline as an essential component.
Quinoline derivative have been found to possess other biological activites such as antibacterial,
antifungal, anticacer, anti-inflammatory, antihypertensive ,antiviral , inhibitits the enzymes such as
alpha-amylase glucosidase.

3. Imidazole:-
Now here we introduced the imidazole ring and how imidazole as essential part of many natural
compounds such as histidine and histamine.
Imidazole and its derivative have occupied a unique place in the field of medicinal and
agrochemical industries.
Imidazole containing molecules i.e.,
Tioconazole, sertaconazole, clotrimazole and bifonazole are effective antifungal drugs.
Imidazoles derivative found to possess various Pharmacological properties such as antioxidant,
anticancer anti-inflammatory antiviral, antitubercular.

4. Synthesis of Quinoline, Hydroquinoline and their Derivatives:-
N-phenylacetamide
2- Chloroquinine-3-carbaldehyde
3-[4-(4-Chlorophenyl)-5-phenyl-
1H-imidazole-2-yl] quinine-2-ol
OH

5. Mechanism:-
Step:1
Dimethyl formamide
(DMF)
Phosphorus chloride
Oxide
Vilsmeier Haack Reagent

6. Step:-2
N-phenylacetamide Vilsmeier Haack Reagent
2- Chloroquinine-3-carbaldehyde
2- Chloroquinine-3-carbaldehyde
3-[4-(4-Chlorophenyl)-5-phenyl-1H-
imidazole-2-yl] quinine-2-ol
Cl
OH

7. Anti-Oxidant activity:-
 The antioxidant activity study of our synthesized
compound were carried out by using DPPH
method.
 The different cocenteration of stock solution ( 10
, 50 and 100 ug/ml ) of synthesized compound
were prepared by using methanol.
 0.1 N 1,1 diphenyl hydrazyl (DPPH) in methanol
added to the above stock solutions and mixed
uniform .
 The resulting solution was kept in dark for 20
min at room temperature .
 Then the absorbunce of the solution was
measured at 517 nm taking a refrence
BHA(Butylated Hydroxyanisole) .
 % Inhibition= ( Control OD – Sample OD)
Control OD
Figure-1; Antioxidant activity of compound and
their derivative.
* 100

8. Anti-bacterial Activity:-
Antibacterial activity on Escherichia coli , Bacillus subtilis megaterium and salmonella typhi was
perform for quinoline derivative by using agar well diffusion method described by pere et al.
taking ciprofloxacin as a standard. Initially the bacterial cultures were incubated at 37 degree for
18 hour in a media. The agar plates in the media were prepared and on each agar plate
Previously incubated culture was spread uniformly. Then plates were allowed to keep it for 20
min and wells were filled with 500 ug/ml concentration of synthesized compounds. The
diameter of zone inhibition was recorded after the plates were incubated at 37 degree for 24
hour.

9.  Application of Quinoline Derivative:-
Quinoline Derivative
Anti-Malarial
Anti-bacterial
Anti-Fungal
Anti-HIV
Anti-tubercular
Anti-inflammatory
Anticancer
Anti-Oxidant
Quinoline Derivative

10. Spectral Data:-
Molecular Formula:- C24H16ClN3O
Yield:- 84%
M.P:-221-223 degree
FT-IR (KBr): 1H-NMR [(500 MHz) , DMSO-d6]:
3418 c.m-1 (N-H)
3030.5 c.m-1 (Ar-H)
1617c.m-1 (C=C)
1573.6 c.m-1 (C=N)
1418.4 c.m -1 (C-O)
7.26 (m,6H) Ar-H
7.50(m,3H) Ar-H
7.58 (m,3H) Ar-H
7.94(m,1H) Ar-H
8.81(s,1H) Ar-H
12.368(s,1H) OH
12.42(s,1H) NH
OH

11.  Quinoline ring based derivative:-

12. Reference: Indian Journal of Chemistry , Section-B,
December 2021.