Presented by:7.
Deepak Bhosale,
27.Prerana Ghuli,28.Sachin Giri,
42.Shruti Kamble, 74.Omkar Patil
Guide: Ms. A. S. Patil
Annasaheb Dange College of B.
Pharmacy, Ashta (2024-25) 1.
• Heterocyclic compounds are organic molecules containing rings with nitrogen, oxygen, or sulphur atoms, essential in
pharmaceuticals and agriculture.
• 1,3,4-Oxadiazole derivatives are a key class of heterocycles known for diverse biological activities: Antibacterial,
antifungal, anti-inflammatory, anticancer, antitubercular, antiviral properties.
• Oxadiazoles act as bio isosteres of amides and esters, offering: Improved hydrolytic and metabolic stability, enhanced
pharmacokinetics and in vivo performance.
• The oxadiazole ring is present in several marketed drugs (e.g., Isradipine - Ca++ channel blocker).
• These compounds are targets in drug discovery programs for: Tyrosine kinase inhibitors, Histamine H3 receptor
antagonists, Antimicrobial and anticancer agents.
• Need for new antimicrobial agents arises due to increasing drug resistance among pathogens. Microwave-assisted
synthesis offers several advantages: Faster reaction rates (minutes instead of hours), higher product yields with fewer
impurities, eco-friendly, energy-efficient, and scalable method. 2.
• Somani. R. R. et al 1, a review on oxadiazole; a biologically important heterocycle.
• Srivastav sachit, et al 8, Studies on Synthesis and biological evaluation of 1,3,4 Oxadiazole derivatives.
3.
1. Nitrogen heterocyclic compounds play a vital role in the metabolism of all living cells, which are widely distributed in
nature and essential to life. The essential amino acids, pyrimidine and purine bases of genetic materials, DNA, proline,
oxygen transporting pigments, hemoglobin are some of the important biomolecule which incorporate nitrogen
heterocyclic system in their structures.
2. Azole nucleus shows various pharmacological activity.
3. In view of the above mentioned facts and in continuation of our interest in the synthesis of heterocycles containing
1,3,4-oxadiazole moiety to identify new candidate that may be value in designing new, potent, selective and less toxic
antimicrobial agents.
4. Microwave assisted organic synthesis as a green synthetic approach is powerful technique. The technique offers
simple, clean, fast, efficient, and economic for the synthesis of a large number of organic molecules.
4.
1. Synthesis of 2, 5 disubstituted 1,3,4 oxadiazole derivatives.
2. Determination of melting point, percentage yield.
3. Characterization of synthesized compounds by TLC, IR, 1H-NMR & MS.
4. Screening of synthesized compounds for anti- microbial activities etc.
5.
• Methods- By Conventional Method and Microwave Technique (Catalyst).
• Step 1st: Synthesis of ethyl 1- hydroxy naphthalene- 2-carboxylate. (compound 1)
Step 2nd: Synthesis of 1 hydroxynaphthalene-2-carboyhydrazide. (compound 2)
Step 3rd: Synthesis of 2(5amino-1,3,4 oxadiazole 2yl) naphthalene1- ol. (compound 3)
Step 4th: Synthesis of 2-{5-[(E)- substituted benzylidene amino)]1,3,4 oxadiazole-2–yl} napthalene-1-ol by
using different aldehydes. (compound 4a1to 4a5)
• TLC used for monitoring reactions.
6.
7
Compound 3: 2-(5-amino-1,3,4-oxadiazol-2-yl)
naphthalen-1-ol
OH N N
NH2
O
Sr. No. Functional gr. Std. Range (cm-1)
1. ( -OH ) Str 3200-3600
2. (C-O-C ) 1050-1150
3. C- H aromatic Str 3000-3100
4. (C=C) Str 1500-1430
5. N – H bend 1550-1650
6. (C=N) Str 1620-1680
7. ( C-H ) aromatic bend 690-900
2-{5-[(2-hydroxybenzylidene)amino]-1,3,4-
oxadiazol-2-yl}naphthalen-1-ol
HO
OH N N
N CH
O
Sr. No. Functional gr. Std. Range (cm-1)
1. ( -OH ) Str 3200-3600
2. (C-O-C ) 1050-1150
3. ( C- N) ) Str 3000-3100
4. (C=C) Str 1500-1430
5. Ar Str 1550-1650
6. (C=N) Str 1620-1680
7. ( C-0) Str 690-900
2-{5-[(3,4,5-trimethoxybenzylidene)amino]-
1,3,4-oxadiazol-2-yl}naphthalen-1ol
OCH3
OH N N
N CH OCH3
O
OCH3
Sr. No. Functional gr. Std. Range (cm-1)
1. ( -OH ) Str 3200-3600
2. (C-O-C ) 1050-1150
3. ( C- N) ) Str 3000-3100
4. (C=C) Str 1500-1430
5. Ar Str 1550-1650
6. (C=N) Str 1620-1680
7. ( C-0) Str 690-900
2-{5-[(4-methoxybenzylidene)amino]-1,3,4-
oxadiazol-2-yl}naphthalen-1-ol
OH N N
N CH OCH3
O
Sr. No. Functional gr. Std. Range (cm-1)
1. ( -OH ) Str 3200-3600
2. (C-O-C ) 1050-1150
3. C- H aromatic Str 3000-3100
4. (C=C) Str 1500-1430
5. N – H bend 1550-1650
6. (C=N) Str 1620-1680
7. ( C-H ) aromatic bend 690-900
2-{5-[(4-bromobenzylidene)amino]-1,3,4-oxadiazol-2-
yl}naphthalen-1-ol
OH N N
N CH Br
O
Sr. No. Functional gr. Std. Range (cm-1)
1. ( -OH ) Str 3200-3600
2. (C-O-C ) 1050-1150
3. C- H aromatic Str 3000-3100
4. (C=C) Str 1500-1430
5. N – H bend 1550-1650
6. (C=N) Str 1620-1680
11.
7. ( C-H ) aromatic bend 690-900
2-{5-[(4-chlorobenzylidene)amino]-1,3,4-oxadiazol-2-
yl}naphthalen-1-ol
OH N N
N CH Cl
O
Sr. No. Functional gr. Std. Range (cm-1)
1. ( -OH ) Str 3200-3600
2. (C-O-C ) 1050-1150
3. C- H aromatic Str 3000-3100
4. (C=C) Str 1500-1430
5. N – H bend 1550-1650
6. (C=N) Str 1620-1680
11.
7. ( C-H ) aromatic bend 690-900
Antibacterial screening results of synthesized compounds measuring the zone of
inhibition in millimeter
14.
Antifungal screening results of synthesized compounds measuring the zone of
inhibition in millimeter.
15.
• IR spectra of synthesized compounds were recorded using JASCO FTIR 4100.
• The IR spectra of synthesized compounds were presented above.
• The H1- NMR Spectra of all synthesized compounds were obtained in DMSO solution with TMS as an internal standard.
• The NMR spectra of synthesized compounds were presented above.
• The structural elucidation of the synthesized compounds was done by the interpretation of the IR, NMR.
• MS analysis confirmed the satisfactory characteristics of the synthesized compound.
• The entire synthesized compounds were screened for anti-microbial activities.
• E. coli, it was observed that the compound 4a1,4a2,4a5, shown high antibacterial activity. For B.substilis compound 4a1,4a2
shown high activity. For S.typhi compound, 4a1 shown high activity which was compared with standard drug ciprofloxacin.
• For C. albicans 4a1, 4a5, shown high antifungal activity.
16.
• Successfully synthesized 2,5-disubstituted 1,3,4-oxadiazole derivatives.
• Microwave-assisted synthesis proved to be an effective and eco-friendly method
• Structural confirmation of synthesized compounds was done through: Melting Point analysis, TLC, IR, NMR, MS.
• The synthesized oxadiazole derivatives exhibited promising antimicrobial activity against: Gram-positive bacteria
(e.g., Staphylococcus aureus, Bacillus subtilis), Gram-negative bacteria (e.g., Escherichia coli, Salmonella typhi).
• Among all compounds, derivatives 4a1 and 4a5 showed the highest antimicrobial activity, comparable to standard
Ciprofloxacin.
• The study highlights the potential of oxadiazole scaffolds as lead structures for developing novel antimicrobial agents.
• Microwave-assisted synthesis can be considered a viable alternative to conventional methods for rapid and efficient
drug synthesis.
• The findings support further optimization and SAR (Structure-Activity Relationship) studies to enhance biological
activity. 17.
1) Rakesh R. Somani et al , Oxadiazole: A biologically important heterocycle. Der Pharma Chemica ,1 (1),2009,130-140.
2) Ashtekar, et al, QSAR study on 2, 5-disubstituted 1,3,4 oxadiazole as antifungal agents. International Journal of Research
in Pharmacy and Chemistry, 4(1), 2014, 26-33.
3) Laxmi Kant Sharma et al, Green synthesis of 2-amino-5-substituted-1,3,4 Oxadiazole at the platinum anode in acetic
acid, Indian Journal Of Chemistry, 50(B),2011,110-114.
4) Savita et al, Green revolution in chemistry by microwave assisted synthesis; a review. modern chemistry, Science
Publishing Group, 1(3), 2013, 22-25.
5) Santhya Saigal et al, A Facile ring transformation of 5-oxazolone derivative of new 1,3,4 oxa (thia) diazolo (3,2-a)
pyrimidin-5-one. Indian Journal of Chemistry 34,1995 500-503.
6) K. Reddy et al. Cyclization by dehydrosulphurization of 1-(-aminobenzoyl)-4-aryl-3 thiosemicarbazide, formation of
1,3,4- benzotriazepinones, 1,3,4- thiadiazol & 1,3,4 oxadiazoles. Indian Journal of Heterocyclic Chemistry, 7,1997,17-20.
