2. 2
SR. N0. NAME OF CHAPTER
1 TITLE.
2 INTRODUCTION
3
AIM AND OBJECTIVE:
4
PLAN OF WORK
5 EXPERIMENTAL WORK
6
PROPOSED WORK IN FUTURE
7
REFERENCES
CONTENTS
3. INTRODUCTION:
3
•Triazoles
Triazole refers to either one pair of isomeric chemical compound having membered
ring of two carbon atom and three nitrogen atoms. The two isomers are (Fig:1)
NH
N
N
1,2,3 triazol
NH
N
N
1,2,4 triazol
The derivatization of Triazole ring is based on the phenomenon of bioisosterism in
whichreplacement of oxygen of oxadiazole nucleus with nitrogen triazole analogue. Out of the
twotriazoles 1, 2, 4- triazole has wide variety of activity.Triazole moiety is an important
andfrequent insecticide, agrochemical structure feature of many biological active compound as
cyto chrome p450 enzyme inhibitors and peptide analog inhibitor. The azole class of
antifungalagent is chemical either an imidazole or a triazole group joined to an asymmetric
carbon atom astheir functional pharmacophore treatment for these infection azole like
antifungal agent are Ketoconazole, Fluconazole , Voriconazole and Ptraconazole 1, 2, 4-triazole
are as analgesic antiasthmatic, antibacterial, anticholinergic activity.
4. Triazole is heterocyclic ring in which In the past years, some azoles derivatives were developed as
new antimicrobial agents, for instance, linezolid and eperezolide are currently used for the treatment
of multidrug-resistant gram-positive infections. There are number of antimicrobial compound
containing a 1, 2, 4-triazole ring in their structures such as fluconazole, itraconazole, ravuconazole
CHEMISTRY OF TRIAZOLE
Triazole refers to either one of a pair of iso mericchemical compounds with molecular
formula C2H3N3, having a five-membered ring of two carbon atoms and three nitrogen
atoms.1,2,4-Triazole is one of a pair of isomericchemical compounds with molecular
formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms
and three nitrogen atoms. 1,2,4-Triazole is a basic aromaticheterocycle. 1,2,4-Triazole
derivatives find use in a wide variety of applications, most notably as antifungals such as
fluconazole and itraconazole.[
The ring structure appears in certain N-heterocyclic carbenes.
The two isomers are:
N
N
H
N
5
1
2
3
4 N
N
H
N
5
1
2
3
4
1,2,3-Triazole 1,2,4-Triazole
6. 6
Sr.NO. Property Value
1 Molecular formula C2H3N3
2 Molar mass 69.065
3 Nature white solid
4 melting point 120-21 o C
5 boiling point 260oC
6 Solubility soluble in water
7 Acidicity at PH 2.2
8 Basicity at 10.3 PH
9 Flash point 140
7. 7
REVIEW OF LITERAURE:
1) Birsen Tozkoparan, Nisren Gokhan, Goknur Aktay, Hacettepe University, Turkey in the year
2000 has synthesized 6-Binzylidenethiazole-triazole substituted with Ibuprofen. 4
N
N
N
N
N
S
Ar
Ar=(a)-C 6H5,
(b) -C6H4-Cl(0)
(c) -C6H3-(Cl) 2(0,P)
2) Dave T. P., Purohit D. H., Akbari J. D., Purohit D. H., Joshi H. S. University of Rajkot in the
year 2006, have synthesized thiazolidinones and Mannich bases of 4-amino-3-mercapto-5-pyridine-
yl-[1, 2, 4]-triazole for their pharmacological action.
N
N
N
N
N
S
SH
O
R
N
N
N
NH2
S
N
CH3
R=4-Cl-C6H5.2-Cl-C6H5,
2-OH-C6H5
8. Ravi T.K., Raj Kennan at Coimbatore, in the year 2003. Synthesized 1, 2, 4-triazole derivative from
salicylic acid and anthranilic acid for their antimicrobial potency.6
N
N
N
SH
R
OH
N
N
+
O
N
N
N
NH2
SH
R
Udupi R.H., Kulkarni V.M., Sudheendra S, at Raichur, in the year 2002, synthesized 1, 2, 4-triazoles
from Isoniazid and he got moderately active anti-inflammatory as well as antimicrobial agent.7
N
N
N
N
N
S
Ar
Ar=(a)-C 6H5,
(b) -C6H4-Cl(0)
(c) -C6H3-(Cl) 2(0,P)
9. 9
SCHEME OF RESEARCH WORK
COOH
NH2
P-Amino Benzoic Acid
1
NH2
COOCH 3
H2SO4
Ethanol
Benzocaine
2
ethanol
hydrazine hydrate
NH2
COO
-
NH
-
NH2
4-Amino Hydrazide Ester
3
KOH
CS2
reflus 20 hrs
N
H2
O
N N
SH
5(4-Amino Phenyl)1,3,4-Oxidazole,2-Thiol
4
ethanol
N
S
NH2
Substituted 2-amino benzothiazole
N
N N
SH
N S
R
4
R
3
R
2
R
1
N
H2
5-(4-aminophenyl)-4-(1,3-benzothiazole-2-yl)-4H-1,2,4-triazole-3-thiol
5
10. 10
AIM AND OBJECTIVE:
To establish the scheme of proposed compound on the basis of literature survey.
To achieve synthesis of Para amino benzoic acid derivities.
To achieve the synthesis of series of Synthesis of derivative as per the scheme.
To establish the structure of synthesized compounds by IR, 1H-NMR, CHN and MASS
spectroscopy.
Biological screening of title compounds for Anti fungal and Anti-bacterial activity, Anti
inflammatory activity and analgesic activity, and other activities if possible like Anti depressant
activity, Anti TB/ Anti diabetic activity/Anti cancer activity.
QSAR study of synthesized compounds and prediction of ADMET parameter.
11. 11
PLAN OF WORK:
To carry out the literature survey and review of imidazole derivatives.
Procurement of chemicals required for synthesis.
Procurement of apparatus.
To establish the scheme of proposed compound on the basis of literature survey.
To achieve synthesis of 1,2,4 trisubstituted imidazol-5-one as per the scheme.
To achieve the synthesis of series of Synthesis of derivative as per the scheme.
To carry out the preliminary characterization such as physical constant determination and to
check purity by TLC.
To confirm the structure of synthesized compounds by IR, 1H-NMR, CHN and MASS
spectroscopy.
The synthesized compounds will be screened for Anti-fungal and Anti-bacterial activity, Anti
inflammatory and analgesic activity, Anti depressant activity, Anti TB/ Anti diabetic activity/Anti
cancer activity.
12. 12
PROPOSED WORK IN FUTURE
1.Spectral characterization :
The targeted compounds will be synthesized and characterized by FT-IR
,1HNMR and MASS spectra's.
2.Biological Screening:
The synthesized compounds will be screened for antimicrobial activity.
Screening of synthesized compounds for other possible activity.
Anti-Cancer activity.
Impurity Profile of compound.
3.QSAR studies of synthesized compounds and prediction of ADMET parameters.
4.Molecular Docking
5.Models for Antimicrobial activity.
14. 14
1. Willams, D. A., Lemke,T.L., 2002. Foye’s, Principle of medicinal chemistry. 1112.
2. Kumari, Shalini., Sharma, Pramod Kumar., Kumar Nitin.,2010. Pelagia Research Library. 1,
36-47.
3. Theresa, M. Tallon., Synthesis Of Triazole Schiff Base Ligands, Their Silver(I) Complexes
And Their Activities Against Candida Albicans,A Thesis Submitted To The National
University Of Ireland In Fulfilment Of The Requirement For The Degree Of Doctor Of
Philosophy Department of Chemistry, The National University of Ireland, Maynooth.
4. Asghar, Davood., Eskandar, Alipour., Abbas, Shafiee., 2008. Turk J Chem. 32, 389 – 395.
5. Bhatnagar, A., Sharma, P. K., Kumar, N., 2011. International Journal of PharmTech
Research. 3, 268-282.
6. Chawla, Anshul., Sharma, Ashu., 2012. Scholars Research Library. 4, 116-140.
7. Block, John H., Beale, John M., 2002.Wilson and gisvold’s textbook of organic medicinal and
pharmaceutical chemistry,Lippincott Williams and Wilkins. 217-279.
8. Roman, G., Riley, J.G., Vlahakis, J. Z., Kinobe, R.T., 2007. Bioorg. Med. Chem. 15, 3225–
3234.
REFERENCES:
