ISSN: 2410-9649 Deeba et al / Chemistry International 4(4) (2018) 206-215 iscientic.org.
206
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Article type:
Research article
Article history:
Received February 2018
Accepted June 2018
October 2018 Issue
Keywords:
1,3,4-oxadiazole
Hydrazones
Copper complexes
Antibacterial
Antifungal activities
A series of novel 1, 3, 4-oxadiazole analogues was synthesized from cyclization of
hydrazones of substituted 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-
naphthyridine-3-carbohydrazides were prepared from nalidixic acid. The
structures of synthesized oxadiazole derivatives and their copper complexes
were elucidated on the basis of FTIR, elemental analyses,
1
H-NMR and atomic
absorption spectral analysis. It was observed from spectral data that metal ligand
ratio was 1:1 in all copper complexes and they were bidentate, coordination was
found to be done through oxygen of 4-oxo group and nitrogen of oxadiazole ring.
The synthesized compounds were further evaluated with biological activities and
compared with parent hydrazones. Copper complexes possess antibacterial and
antifungal activities better than the oxadiazoles while they have better
antioxidant activity then copper complexes. Parent hydrazones were better in all
biological activities than synthesized oxadiazoles.
© 2018 International Scientific Organization: All rights reserved.
Capsule Summary: A series of novel 1,3,4-oxadiazole analogues was synthesized from cyclization of hydrazone. The
synthesized compounds showed considerable biological activities than synthesized oxadiazoles.
Cite This Article As: F. Deeba, N. Abbas, M. T. Butt, R. A. Khan, M. M. Ahsan and M. A. Khan. Synthesis, characterization and
biological activities of 1,3,4-oxadiazole derivatives of nalidixic acid and their copper complexes. Chemistry International 4(4)
(2018) 206-215.
INTRODUCTION
Nalidixic acid (1-ethyl-7-methy-1,8-naphthyridine-4-one-3-
carboxylate, C12H12N2O3,) was the first developed compound
of the family of quinolone and 1,8-naphthyridines. It was
described by Lesher and his coworkers in (Lesher et al.,
1962) and since then it has been used extensively in therapy
(Aggarwal et al., 2010; Cotton et al., 1999; Miessler and Tarr,
1999). 1, 8-naphthyridine derivatives have been investigated
for a long period of time to report complexation properties
and medicinal uses e.g., possess antibacterial, anti-
inflammatory, anti-hypertensive and anti-platelet activities.
After the discovery of first quinolone, nalidixic acid,
medicinal and industrial chemists have made numerous
structural modification and new quinolones (Chen et al.,
2001; Roma et al., 2000) have continually been made, in the
hope of incremental microbiological advantages over
Nalidixic acid which displays remarkable potency against
gram negative as well as gram positive and anaerobic
organisms (Das, 1990).
Chemistry International 4(4) (2018) 206-215
Synthesis, characterization and biological activities of 1,3,4-oxadiazole derivatives
of nalidixic acid and their copper complexes
Farah Deeba
1
, Naeem Abbas
1,*
, Muhammad Tahir Butt
1
, Rauf Ahmad Khan
1
, Muhammad Muneeb
Ahsan
2
and Misbahul Ain Khan
3
1
Center for environmental protection studies, PCSIR Laboratories Complex, Lahore Pakistan.
2
ICET, Institute of Chemical Engineering and Technology, University of the Punjab, Lahore, Pakistan
3
Professor Emeritus, Institute of Chemistry, Islamia University Bhawalpur, Pakistan
*Corresponding author’s E. mail: naeemchemist@gmail.com
ARTICLE INFO ABSTRACT