Synthesis, Antibacterial Evaluation and QSAR of  α-Substituted-N4-Acetamides of Ciprofloxacin and Norfloxacin

Qandil, Amjad M.; Al-Zoubi, Lorca O.; Al‐Bakri, Amal G.; Amawi, Haneen; Al-Balas, Qosay; Alkatheri, Abdulmalik; Albekairy, Abdulkareem M

doi:10.3390/antibiotics3030244

Cited by 13 publications

(7 citation statements)

References 31 publications

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“…The analogues (Series 1) were synthesized as shown in Scheme 4 starting from the commercially available, CPX. The carboxylic acid sub‐series was obtained in single amidation reaction of CPX at its N‐15 with acyl/carbamoyl/sulfonyl chloride or cholesteryl chloroformate utilizing literature reported method (Qandil et al., ) to afford analogues 9–12 . The nucleophile substitution S N 2 using propargyl bromide at the N‐15 resulted in 13 .…”

Section: Resultsmentioning

confidence: 99%

“…It is noteworthy indicating that following the procedure described by Qandil et al. (), synthesis of the alkyne intermediate 13 was optimized by changing the solvent system from dry dichloromethane to monoglyme‐DMSO mixture (5:1) upon reflux to improve solubility of the reagents which beneficially resulted in an increase in its yield from 54% to 66%.…”

Section: Resultsmentioning

confidence: 99%

“…These were evidence of the presence of the fluoroquinolone pharmacophore. The former doublet is ascribed to the coupling of H‐5 with F in position 6 in the aromatic system (Qandil et al., ). This distinctive splitting pattern was also seen in the 13 C NMR spectra where C‐F coupling constants ( J ) for C‐5, C‐6, and C‐7 were 23, 248, and 10 Hz which is in accordance with previous findings (Qandil et al., ) and further confirms the presence of the fluoroquinolone pharmacophore in the synthesized compounds.…”

Section: Resultsmentioning

confidence: 99%

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Design, synthesis, and antimycobacterial activity of novel ciprofloxacin derivatives

et al. 2019

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Tuberculosis is the deadliest infectious disease affecting humankind with a death toll of approximately 1.7 million people in 2016. The increasing prevalence of multidrug‐resistant strains of the causative pathogen, Mycobacterium tuberculosis (Mtb) which results in reduced effectiveness of the current therapies, underscores the urgent need for the development of new antitubercular drugs. In the search for such drugs, we investigated two series of ciprofloxacin (CPX) derivatives (analogues and hybrids). We herein report the design, synthesis, and biological activity of these series against the human virulent Mtb H37Rv strain in vitro. The small propionyl analogue 11 (MIC90 1.6 μM; SI > 61) and the large cholesteryl hybrid 32 (MIC90 2.0 μM; SI > 6) were the most active derivatives, comparable to CPX (MIC90 1.8 μM). However, the slightly less active but non‐cytotoxic para‐fluorobenzyl hybrid 28 (MIC90 3.7 μM; SI 27) was more selective toward bacteria than 32. Thus, the CPX derivatives 11 and 28 were identified as preferred antitubercular hits for further investigation including distribution, metabolism and pharmacokinetic parameters determination and in vivo activity assessment in animal models.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Design, synthesis, and antimycobacterial activity of novel ciprofloxacin derivatives

et al. 2019

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“…7-(4-(2-Chloroacetyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ( 2 ) was already reported in the literature and was re-synthesized by our group using the previously reported protocol [45,46]. Light yellow-brown solid; mp = 257–258 °C (lit.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents

et al. 2019

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In an effort to improve the antimicrobial activity of norfloxacin, a series of hybrid norfloxacin–thiazolidinedione molecules were synthesized and screened for their direct antimicrobial activity and their anti-biofilm properties. The new hybrids were intended to have a new binding mode to DNA gyrase, that will allow for a more potent antibacterial effect, and for activity against current quinolone-resistant bacterial strains. Moreover, the thiazolidinedione moiety aimed to include additional anti-pathogenicity by preventing biofilm formation. The resulting compounds showed promising direct activity against Gram-negative strains, and anti-biofilm activity against Gram-positive strains. Docking studies and ADMET were also used in order to explain the biological properties and revealed some potential advantages over the parent molecule norfloxacin.

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“…The reaction was filtered and resulting solid was dissolved in dichloromethane, which was given the washings of saturated solution of sodium chloride (3 × 30 mL). The organic layer collected and dried over anhydrous sodium sulphate, pure sample was obtained after the removal of solvent as shown in Scheme …”

Section: Methodsmentioning

confidence: 99%

Theoretical molecular predictions and antimicrobial activities of newly synthesized molecular hybrids of norfloxacin and ciprofloxacin

Kaur

Sharad

et al. 2019

Journal of Heterocyclic Chem

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Antibiotics such as norfloxacin and ciprofloxacin are used to treat numerous bacterial infections. The present research work involves the molecular prediction, synthesis, characterization and in vitro antimicrobial activities of molecular hybrids of norfloxacin and ciprofloxacin. First set of compounds involve the substitutions of various amines at third position of ciprofloxacin and norfloxacin. On the other hand, second set of molecular hybrids include the substitution of different amines at seventh position along with linker (─COCH 2 ─). These synthesized compounds were identified by TLC technique and well characterized by various spectroscopic techniques such as IR, NMR,and ESI-MS. Molecular prediction of these newly synthesized compounds have been carried out using the SwissADME, ADMETLab software. Their cytotoxic-

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Synthesis, Antibacterial Evaluation and QSAR of α-Substituted-N4-Acetamides of Ciprofloxacin and Norfloxacin

Cited by 13 publications

References 31 publications

Design, synthesis, and antimycobacterial activity of novel ciprofloxacin derivatives

Design, synthesis, and antimycobacterial activity of novel ciprofloxacin derivatives

Design, Synthesis and Biological Evaluation of New Piperazin-4-yl-(acetyl-thiazolidine-2,4-dione) Norfloxacin Analogues as Antimicrobial Agents

Theoretical molecular predictions and antimicrobial activities of newly synthesized molecular hybrids of norfloxacin and ciprofloxacin

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