New ciprofloxacin–dithiocarbamate–benzyl hybrids: design, synthesis, antibacterial evaluation, and molecular modeling studies

Esfahani, Ensieh Nasli; Mohammadi-Khanaposhtani, Maryam; Rezaei, Zahra; Valizadeh, Yosef; Rajabnia, Ramazan; Hassankalhori, Mahdi; Bandarian, Fatemeh; Faramarzi, Mohammad Ali; Samadi, Nasrin; Amini, Mohammad Reza; Mahdavi, Mohammad; Larijani, Bagher

doi:10.1007/s11164-018-3598-3

Cited by 10 publications

(8 citation statements)

References 21 publications

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“…The MIC values were used to evaluate their antibacterial activity and results were compared with the standard. The lower the MIC values the higher will be the antibacterial potential . The results based on the MICs obtained show that the free ligands have lower antimicrobial activities against the six bacterial strains when compared to ciprofloxacin with the exception of DTL3 and DTL5 which are more active against K. pneumoniae than ciprofloxacin.…”

Section: Resultsmentioning

confidence: 97%

“…The lower the MIC values the higher will be the antibacterial potential. [70][71][72][73] The results based on the MICs obtained show that the free ligands have lower antimicrobial activities against the six bacterial strains when compared to ciprofloxacin with the exception of DTL3 and DTL5 which are more active against K. pneumoniae than ciprofloxacin. In contrast to the parent ligands, the complexes show moderate to excellent antimicrobial activity compared to the reference drug, most especially towards Gram-negative bacteria.…”

Section: Antimicrobial Studiesmentioning

confidence: 96%

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Co(III) N,N′‐diarylformamidine dithiocarbamate complexes: Synthesis, characterization, crystal structures and biological studies

Oladipo

Omondi

Mocktar

2020

Applied Organom Chemis

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Three symmetric N,N‐diarylformamidine dithiocarbamates, N,N′‐bis(2,6‐dimethylphenyl)formamidine dithiocarbamate (DTL1), N,N′‐bis(2,6‐disopropylphenyl)formamidine dithiocarbamate (DTL2) and N,N′‐dimesitylformamidine dithiocarbamate (DTL3), and three unsymmetric ones, N′‐(2,6‐dichlorophenyl‐N‐(2,6‐dimethylphenyl)formamidine dithiocarbamate (DTL4), N′‐(2,6‐dichlorophenyl)‐N‐(2,6‐diisopropylphenyl)formamidine dithiocarbamate (DTL5) and N′‐(2,6‐dichlorophenyl)‐N‐mesitylformamidine dithiocarbamate (DLT6), were reacted with chloridocobalt(III) in water to give Co‐(DTL1)3 (1), Co‐(DTL2)3 (2), Co‐(DTL3)3 (3), Co‐(DTL4)3 (4), Co‐(DTL5)3 (5) and Co‐(DTL6)3 (6). All the dithiocarbamates and complexes were characterized using 1H NMR, 13C NMR, Fourier transform infrared, UV–visible and mass spectra and the purity confirmed by elemental analysis. In addition, crystal structures of complexes 1, 2, 4 and 5 were determined, confirming the formation of mononuclear species in which the Co(III) centers coordinated to six sulfur atoms from three dithiocarbamate ligands resulting in distorted octahedral geometries. All complexes showed moderate to good antibacterial activities against Gram‐negative bacteria Escherichia coli, Salmonella typhimurium, Klebsiella pneumoniae and Pseudomonas aeruginosa even at low concentrations. None of the six were active against Gram‐positive bacterium methicillin‐resistant Staphylococcus aureus and only active against S. aureus at high concentrations. Complexes 5 and 6 were found to be more active than ciprofloxacin against S. typhimurium, E. coli, P. aeruginosa and K. pneumoniae and complexes with chloro‐substituted ligands generally had enhanced activities. Antioxidant activities of the dithiocarbamate salts and their Co(III) complexes were also investigated using DPPH assay and the complexes were found to be more efficient. Complex 2 with an IC50 value of 2.84 × 10−4 mM displayed the highest activity of all compounds tested, even outdoing ascorbic acid. The radical scavenging ability of the complexes followed the order 2 > 1 > ascorbic acid >3 > 4 > 6 > 5.

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Section: Resultsmentioning

confidence: 97%

Section: Antimicrobial Studiesmentioning

confidence: 96%

Co(III) N,N′‐diarylformamidine dithiocarbamate complexes: Synthesis, characterization, crystal structures and biological studies

Oladipo

Omondi

Mocktar

2020

Applied Organom Chemis

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“…SARs reveals that a nitro substituent at the 4-position of the benzyl ring improved the antimicrobial activities compared to the rest of the synthesized derivatives. A molecular docking study of compound B against E. coli showed that the sulfur atom of the dithiocarbamate participated in two interactions with residues Asn46 and Val120, and the ciprofloxacin group also interacted with residues Arg76, Ile78, Pro79, Ile90, and Arg136 in the active site of DNA gyrase 29 . Along the same line, the urease inhibitory and antibacterial activities of the ciprofloxacin-piperazinyl derivatives were proved (Fig.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of new N-thioacylated ciprofloxacin derivatives as urease inhibitors with potential antibacterial activity

Pedrood

Azizian

Montazer

et al. 2022

Sci Rep

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A new series of N-thioacylated ciprofloxacin 3a–n were designed and synthesized based on Willgerodt–Kindler reaction. The results of in vitro urease inhibitory assay indicated that almost all the synthesized compounds 3a–n (IC50 = 2.05 ± 0.03–32.49 ± 0.32 μM) were more potent than standard inhibitors, hydroxyurea (IC50 = 100 ± 2.5 μM) and thiourea (IC50 = 23 ± 0.84 μM). The study of antibacterial activity against Gram-positive species (S. aureus and S. epidermidis) revealed that the majority of compounds were more active than ciprofloxacin as the standard drug, and 3h derivative bearing 3-fluoro group had the same effect as ciprofloxacin against Gram-negative bacteria (P. aeruginosa and E. coli). Based on molecular dynamic simulations, compound 3n exhibited pronounced interactions with the critical residues of the urease active site and mobile flap pocket so that the quinolone ring coordinated toward the metal bi-nickel center and the essential residues at the flap site like His593, His594, and Arg609. These interactions caused blocking the active site and stabilized the movement of the mobile flap at the entrance of the active site channel, which significantly reduced the catalytic activity of urease. Noteworthy, 3n also exhibited IC50 values of 5.59 ± 2.38 and 5.72 ± 1.312 µg/ml to inhibit urease enzyme against C. neoformans and P. vulgaris in the ureolytic assay.

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“…In many researches, designed CFX hybrids have been synthesized, and their structure-activity relationships have been reported. [45][46][47][48] Besides that, CFX is used for the treatment of tuberculosis mainly in cases involving resistance or intolerance to first-line anti-TB therapy as the second-generation FQ drug. [36] Moxifloxacin (MFX), which is a fourth-generation FQ drug, has good bactericidal activity and is used for the treatment of a variety of infections.…”

Section: Introductionmentioning

confidence: 99%

Novel fluoroquinolones containing 2‐arylamino‐2‐oxoethyl fragment: Design, synthesis, evaluation of antibacterial and antituberculosis activities and molecular modeling studies

Kulabaş

Türe

Bozdeveci

et al. 2022

Journal of Heterocyclic Chem

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Novel substituted fluoroquinolone derivatives, compounds 6-20 were designed, synthesized, and evaluated for antituberculosis and antibacterial activity. Antibacterial activities of the compounds were determined and compound 14 was found to be the most potent antimicrobial agent owing to minimal inhibitory concentration (MIC) value of <1.16 μg/μl for all tested bacteria. Further, compounds were tested in vitro for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Most of the compounds showed antimycobacterial effects with 1.56-25.00 μg/ml MIC values. Compounds 14 and 18 were found to be the most active derivatives due to their MIC at 1.56 μg/ml. Selected compounds 11, 14, 17, and 18 were tested for M. tuberculosis DNA supercoiling assay and they had IC 50 values within a range of 6.35-15 μM. Mechanism of binding to DNA gyrase enzymes was evaluated using in silico molecular modeling studies and it was shown that compounds 6-20 adopt a similar binding mode as already known for fluoroquinolone drugs.

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New ciprofloxacin–dithiocarbamate–benzyl hybrids: design, synthesis, antibacterial evaluation, and molecular modeling studies

Cited by 10 publications

References 21 publications

Co(III) N,N′‐diarylformamidine dithiocarbamate complexes: Synthesis, characterization, crystal structures and biological studies

Co(III) N,N′‐diarylformamidine dithiocarbamate complexes: Synthesis, characterization, crystal structures and biological studies

Design and synthesis of new N-thioacylated ciprofloxacin derivatives as urease inhibitors with potential antibacterial activity

Novel fluoroquinolones containing 2‐arylamino‐2‐oxoethyl fragment: Design, synthesis, evaluation of antibacterial and antituberculosis activities and molecular modeling studies

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