Synthesis, Identification, Theoretical Study, and Effect of the New Heterocyclic System from Ciprofloxacin Derivatives on the Activity of Some Liver Enzymes
DOI:
https://doi.org/10.21123/bsj.2022.7502Keywords:
Ciprofloxacin, Liver enzymes, Mannich reactions, Spectrum, SynthesisAbstract
The target of this study was to synthesize several new Ciprofloxacin drug analogs by providing a nucleophilic substitution procedure that provides new functionality at the carboxylic group location. The analogs were synthesized, designed, and characterized by 1HNMR, and FTIR. The synthetic path began from the reaction of ciprofloxacin drug with morpholine to give compound[B], ciprofloxacin derivative was linked with a variety of primary and secondary amines to give compounds[B1-B9]. The above-mentioned prepared compounds [B3 and B5] were applied to liver enzymes, and the increase in the activity of these enzymes was observed. In addition, a theoretical study was conducted to study the energies and properties of the prepared compounds.
Received 6/4/2022
Accepted 8/9/2022
Published Online First 25/11/2022
References
Rabbani MG, Islam MR. Synthesis and Characterization of Some NH-Analogues of Ciprofloxacin on Antibacterial, Antifungal, and Cytotoxic Activities. J Sci Res. 2020 May 1; 12(3): 349-62.
Kassab AE, Gedawy EM. Novel ciprofloxacin hybrids using biology oriented drug synthesis (BIODS) approach: Anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis, topoisomerase II inhibition, and antibacterial activity. Eur J Med. Chem. 2018 Apr 25; 150: 403-18.
Hernández-López H, Sánchez-Miranda G, Araujo-Huitrado JG, Granados-López AJ, López JA, Leyva-Ramos S, et al. Synthesis of hybrid fluoroquinolone-boron complexes and their evaluation in cervical cancer cell lines. J Chem.2019 Jan 20; 2019.
Xu Z, Zhang S, Feng LS, Li XN, Huang GC, Chai Y, et. al. Synthesis and in vitro antimycobacterial and antibacterial activity of 8-OMe ciprofloxacin-hydrozone/azole hybrids. Mol. 2017 Jul 13;22(7):1171.
Abass AM. Synthesis New Liquid Selective Electrodes of Ciprofloxacin Hydrochloride for Determination Ciprofloxacin in Pure form and Pharmaceuticals Preparation. Baghdad Sci J. 2017; 14(4): 787-792.
Zhang GF, Liu X, Zhang S, Pan B, Liu ML. Ciprofloxacin derivatives and their antibacterial activities Eur J Med Chem. 2018 Feb 25; 146: 599-612.
Hooper DC, Wolfson JS. Fluoroquinolone antimicrobial agents. N Engl J Med. 1991 Feb 7; 324(6): 384-94.
Fedorowicz J, Sączewski J. Modifications of quinolones and fluoroquinolones: hybrid compounds and dual-action molecules. Monatsh. Chem. 2018 Jul; 149(7): 1199-245.
Jafar NN, Majeed NS. Microwave-assisted synthesis and biological activity of ester, carbothioate and carbohydrazide derivative compounds of the drug Ciprofloxacin. J Chem Pharm Sci. 2017; 10: 515-21.
Wang R, Yin X, Zhang Y, Yan W. Design, synthesis and antimicrobial evaluation of propylene-tethered ciprofloxacin-isatin hybrids. Eur J Med Chem. 2018; 156: 580-586.
Cipurković A, Horozić E, Ljubijankić N, Odobašić A, Galijašević S, Saletović M. Synthesis and spectral characterization of Fe (II) and Mn (II) complexes with oral fluorouracil pro-drug Capecitibine. Rasayan J Chem. 2017; 10(4): 1381-90.
Pal TK, Alam MA, Hossen J, Paul S, Ahmad H, Sheikh MC. Spectral and Biological Studies on New Mixed Ligand Complexes. J Sci Res. 2018 Sep 1; 10(3): 291-302.
Ljubijankić N, Stanković M, Tešević V, Grgurić-Šipka S, Jadranin M, Begić S, et. al. Cytokinesis block micronucleus assay in human lymphocytes after exposure to Ru (III) thiosemicarbazone complexes in vitro. Rasayan J Chem. 2018; 11(2): 647-52.
Mohammed AA, Suaifan GA, Shehadeh MB, Okechukwu PN. Design, synthesis, and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives. Eur J Med Chem. 2020 Sep 15; 202: 112513.
Saeed AM, Salih ES. Indirect spectrofluorometric method for the determination of cefotaxime sodium, ciprofloxacin hydrochloride, and famotidine in pharmaceuticals using bromate-bromide and acriflavine dye. Baghdad Sci J.2020; 17(1): 66-77.
Ahamed MR, Narren SF, Sadiq AS. The Preparation of some New Mannich and Shiff bases derived from 2-Mercaptobenzimidazole. Baghdad Sci J. 2015; 12(3): 516-26
Sultana N, Arayne MS, Rizvi SB, Haroon U. Synthesis, characterization and biological evaluations of ciprofloxacin carboxamide analogs. Bull Korean Chem Soc. 2011; 32(2): 483-8.
Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc. 1934 Mar; 56(3): 658-66.
Khudhair ZT, Al-Tamimi EO. Synthesis, Identification, Theoretical Study and effect of 1, 3, 4-Oxadiazole Compounds Substituted on Creatinine ring on the activity of some Transfers Enzymes. Res J Pharm Technol. 2019; 12(8): 3581-8.
Satyanarayna, U. Biochemistry, second ed. Books and Allied (P) Ltd., India; 2003. p. 91. www.amazon.com/Biochemistry-Dr-U-Satyanarayana/dp/8187134801
Eddy NO, Ebenso EE. Quantum chemical studies on the inhibition potentials of some penicillin compounds for the corrosion of mild steel in 0.1 M HCl. J Mol Model. 2010 Jul; 16(7): 1291-306.
Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula as a function of the electron density. Phys Rev B. 1988 Jan 15; 37(2): 785.
Singh K, Barwa MS, Tyagi P. Synthesis and characterization of cobalt (II), nickel (II), copper (II), and zinc (II) complexes with Schiff base derived from 4-amino-3-mercapto-6-methyl-5-oxo-1, 2, 4-triazine. Eur J Med Chem. 2007 Mar 1; 42(3): 394-402
Downloads
Published
Issue
Section
License
Copyright (c) 2022 Baghdad Science Journal
This work is licensed under a Creative Commons Attribution 4.0 International License.
How to Cite
