SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF SUBSTITUTED 1,3,4-OXADIAZOLE DERIVATIVE: DERIVED FROM CIPROFLOXACIN
DOI:
https://doi.org/10.22159/ajpcr.2019.v12i9.34712Keywords:
1,3,4-Oxadiazole, Ciprofloxacin, AntimicrobialAbstract
Objective: The purpose of this research is synthesized and evaluates different derivatives of oxadiazole.
Methods: A novel series of substituted 1,3,4-oxadiazole derivative were synthesized by condensing different amine with 1-cyclopropyl-6-fluoro-7- (piperazin-1-yl)-3-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)quinolin-4(1H)-one (III) in the presence of formaldehyde. The structure of these novel synthesized compounds was characterized on the bases of physicochemical and spectral analysis. The title compounds (IVa-h) were screened for antibacterial activity by disc diffusion method.
Results: Substituted 1,3,4-oxadiazole derivative was synthesized, characterized, and evaluated for antibacterial activity. Compounds IVa, IVd, IVe, IVf, and IV h showed enhance activities then ciprofloxacin against all Gram-positive and Gram-negative organisms. Compound IVe showed the highest activity against Staphylococcus aureus and compound IV showed the highest activity against Escherichia coli.
Conclusion: The present study demonstrates the synthesis and characterization of 1,3,4-oxadiazole derivatives derived from ciprofloxacin. These compounds were evaluated for antibacterial activity against different Gram-positive and Gram-negative organism. In some cases, antibacterial activity is found to be enhanced as compared to standard drug ciprofloxacin.
Downloads
References
Patel K, Jayachandran E, Shah R, Javali V, Sreenivasa GM. Synthesis, characterization and anthelmintic activity (perituma posthuma) of new oxadiazole incorporated with imidazole and pyrazole. Int J Pharm Bio Sci 2010;1:1-13.
Shivarama BH, Poojary KN, Bhat KS, Mithun A, Poojary B. Synthesis and anticancer activity studies on some 2-chloro-1, 4-bis-(5-substituted- 1,3,4-oxadiazol-2-ylmethyleneoxy) phenylene derivatives. Indian J Chem 2005;44B:1669-73.
Chandrakantha B, Shetty P, Nambiyar V, Isloor N, Isloor AM. Synthesis, characterization and biological activity of some new 1,3,4-oxadiazole bearing 2-flouro-4-methoxy phenyl moiety. Eur J Med Chem 2010;45:1206-10.
Mistry BD, Desai KR, Intwala SM. Comparative studies of novel oxadiazole derivative having chiral center and their anti-microbial activities. Int J Pharm Pharm Sci 2014;7:195-9.
Upadhyay PK, Mishra P. Design, synthesis and antifungal evaluation of novel substituted 1, 3, 4-oxadiazoles, and 1, 3, 4-thiadiazoles. Int J Pharm Pharm Sci 2015;9:467-70.
El-Emam AA, Al-Deeb OA, Al-Omara M, Lehmann J. Synthesis, antimicrobial and anti-HIV-1 activity of certain 5-(1-adamantyl)-2- substituted thio-1,3,4-oxadiazoles and 5-(1-adamantyl)-3-substituted aminomethyl-1,3,4-oxadiazoline-2-thiones. Bioorg Med Chem 2004;12:5107-13.
Manjunath SY, Biradar R, Basawaraj. Synthesis and anthelminitic activity of triheterocycles: [5(5-substituted-3-phenylindol-2-yl)1, 3, 4-oxadiazole-2-yl thiomethyl] benzimidazols. Indian J Heterocycl Chem 2009;18:321-4.
Almasirad A, Tabatabai SA, Faizi M, Kebriaeezadeh A, Mehrabi N, Dalvandi A, et al. Synthesis and anticonvulsant activity of new 2-substituted-5- [2-(2-fluorophenoxy)phenyl]-1,3,4-oxadiazoles and 1,2,4-triazoles. Bioorg Med Chem Lett 2004;14:6057-9.
Hassan GS, El-Emam AA, Gad LM, Barghash AE. Synthesis, antimicrobial and antiviral testing of some new 1-adamantyl analogues. Saudi Pharm J 2010;18:123-8.
Zareef M, Iqbal R, De Dominguez NG, Rodrigues J, Zaidi JH, Arfan M, et al. Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1, 3, 4-oxadiazole moieties. J Enzyme Inhib Med Chem 2007;22:301-8.
Girges MM. Synthesis and pharmacological evaluation of novel series of sulfonate ester-containing 1,3,4-oxadiazole derivatives with anticipated hypoglycemic activity. Arzneimittelforschung 1994;44:490-5.
Palkar MB, Singhai AS, Ronad PM, Vishwanathswamy AH, Boreddy TS, Veerapur VP, et al. Synthesis, pharmacological screening and in silico studies of new class of diclofenac analogues as a promising anti-inflammatory agents. Bioorg Med Chem 2014;22:2855-66.
Panda J, Patro VJ, Panda CS, Mishra J. Synthesis, characterization, antibacterial and analgesic evaluation of some 1,3,4-oxadiazole derivatives. Der Pharm Chemic 2011;3:485-90.
Siddiqui AA, Islam M, Kumar S. Synthesis and antituberculostic activity of 5-{3’-oxo-6’(substituted phenyl)-2’,3’,4’,5’-tetrahydropyridazin- 2’-yl}methyl-2-substituted 1,3,4-oxadiazole. Der Pharm Lett 2010;2:319-27.
Kataria AK, Khan SA, Alam MM, Husain A, Akhtar M, Khanna S, et al. Synthesis of some new 2-(substituted-phenyl)-5-(N,N-diphenylaminomethyl)-1,3,4-oxadiazoles: A safer anti-inflammatory and analgesic agents. Acta Pol Pharm 2011;68:381-6.
Zhanel GG, Walkty A, Vercaigne L, Karlowsky JA, Embil J, Gin AS, et al. The new fluoroquinolones: A critical review. Can J Infect Dis 1999;10:207-38.
Chourasia A, Agrawal S. Development and evaluation of ciprofloxacin hydrochloride loaded ocular insert by using “Plantago ovata” as natural polymer. Int J Curr Pharm Res 2018;10:79-88.
Hooper DC, Wolfson JS. Fluoroquinolone antimicrobial agents. N Engl J Med 1991;324:384-94.
Ludlam HA, Barton I, White L, McMullin C, King A, Phillips I, et al. Intraperitoneal ciprofloxacin for the treatment of peritonitis in patients receiving continuous ambulatory peritoneal dialysis (CAPD). J Antimicrob Chemother 1990;25:843-51.
Yamashita Y, Ashizawa T, Morimoto M, Hosomi J, Nakano H. Antitumor quinolones with mammalian topoisomerase II mediated DNA cleavage activity. Cancer Res 1992;52:2818-22.
Furniss B, Hannaford AH, Smith PW, Tachell AR. Vogel’s Text Book of Practical Organic Chemistry. 5th ed. London: Prentice Hall; 1998. p. 1077.
Robbert DS. Clinical Analysis, Microbiology, Remington’s Pharmaceutical Sciences. 18th ed. Peninisilvenia: Mack Publishing Company; 1991. p. 524-7.
Tortora GJ, Funke BR, Case CL. Microbiology: An Introduction. 9th ed. San Francisco: Person Education Inc.; 2008. p. 601-2.
Pelczar M, Reid R, Cohn E. Antibiotics and other chemotherapeutic agents. In: Microbiology. TMH ed. Noida: TATA-McGraw-Hill Publishing House; 1989. p. 466-93.
Published
How to Cite
Issue
Section
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.
