Synthesis and antibacterial activity of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones

Shafiee, Abbas; Emami, Saeed; Ghodsi, Shahram; Najjari, S.; Sorkhi, Maedeh; Samadi, Nasrin; Faramarzi, Mohammad Ali; Foroumadi, Alireza

doi:10.1007/bf03245841

Cited by 10 publications

(4 citation statements)

References 20 publications

(21 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthetic pathways for the synthesis of intermediates (2 g-r) , the target compounds (4a-x) and their physical data are shown in Table 1 . Compounds (2 g-r) were prepared by stirring the ketone analogues with excess amounts of hydroxylamine, O -methylhydroxylamine and O -benzylhydroxylamine hydrochloride salts in methanol at room temperature [ 20 – 22 ]. Then, the reaction of 3 with compounds (1a-f) and (2 g-r) in DMF in the presence of NaHCO 3 at 25 °C afforded corresponding N -[2-(aryl-3-yl) ethyl] piperazinyl quinolones (4a-x) which was purified by recrystallization from methanol-chloroform.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, different derivatives containing 2-oxoethyl or 2-oximinoethyl derivative attached to the piperazine ring at C-7 position were synthesized [ 13 ]. In addition, the attachment of thiophene [ 17 , 18 ], furan [ 19 ], substituted phenyl [ 20 ] and coumarin [ 21 , 22 ] to piperazine ring was also investigated by our research team. In continuation of our expertise in this field [ 23 – 25 ], we report some novel analogues of sarafloxacin 3 , possessing α-haloketones- (1a-f) , hydroxyimino- (2 g-l) , methoxyimino- (2 m-r) and benzyloxyimino (2 s-x) -functionalized piperazine as C-7 substituents and evaluate their antibacterial activity against Gram-positive and Gram-negative bacteria.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

N-substituted piperazinyl sarafloxacin derivatives: synthesis and in vitro antibacterial evaluation

et al. 2018

View full text Add to dashboard Cite

BackgroundFluoroquinolones (FQs) are compounds of major interest with broad antimicrobial activities against community and hospital-acquired infections such as respiratory tract infections (nosocomial pneumonia, chronic bronchitis and tuberculosis), skin and soft tissue infections, bone and joint infections, intra-abdominal infections and sexually transmitted diseases. This broad range of activities along with favorable pharmacokinetic and low toxicity introduced this class of compounds as important antimicrobial chemotherapy agents. The rapid increase in prevalence of FQs resistant microbes in environment motivated medicinal chemists to discover new quinolone-based compounds with potent activities against Gram-positive bacteria.MethodsThe designed compounds were prepared through the two-component reaction between aromatic α-haloketones or α-halooximes and sarafloxacin in the presence of NaHCO3 in DMF, affording the corresponding N-[2-(aryl-3-yl) ethyl] piperazinyl quinolone derivatives in good yields. All synthesized compounds were evaluated for antibacterial activities against Gram-positive [Staphylococcus aureus ATCC 6538p, Micrococcus luteus, ATCC 1110, Staphylococcus epidermidis ATCC 12228 and Bacillus subtilis ATCC 6633] and Gram-negative [Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 10031 Pseudomonas aeruginosa ATCC 9027 and Serratia marcescens PTCC 1111] bacteria.ResultsThe antibacterial activities of 24 new compounds were reported as MIC values in comparison to sarafloxacin. The most active compound, 4 g, exhibited similar inhibitory activity against Gram-positive bacteria including S. aureus, S. epidermidis and B. subtilis compared to positive control. Furthermore, benzyloxime incorporated derivatives (4 s-4x) showed poor activity against all tested strains, except 4x.ConclusionThe obtained results indicated that the synthesized compounds containing substituted piperazine moiety at the C-7 position displayed same or weak inhibitory activities compared to sarafloxacin. Graphical abstractᅟ

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

N-substituted piperazinyl sarafloxacin derivatives: synthesis and in vitro antibacterial evaluation

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Compound 2 was converted to 3- (bromoacetyl) coumarin oxime 2a by stirring with 3 equivalents of hydroxylamine hydrochloride in methanol at room temperature. Similarly, the 3-(bromoacetyl) coumarinoxime ethers 2b, 2c was obtained by reaction of compound 2 with methoxy amine hydrochloride or O - benzylhydroxylamine hydrochloride ( 22 - 23 ). Reaction of quinolones with α- bromo ketone 2 or α- bromo oxime derivatives 2a-c in DMF, at the presence of NaHCO 3 at room temperature gives related ketones and oxime derivatives 6a-6l, respectively ( Table 1 ) ( 22 - 23 ).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Some New Thiazolidinedione Derivatives Containing a Coumarin Moiety for their Antibacterial and Antifungal Activities

Valadbeigi¹,

Ghodsi²

2017

Med chem

View full text Add to dashboard Cite

Simple coumarins and analogues are large class of compounds that have attracted their interest for a long time due to their biological activities. They have shown to be useful as anti-tumoural, anti-HIV agents and as CNS active compounds. Furthermore, they have been reported to have multiple biological activities (anti-coagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics in this field of research. A new series of thiazolidinedione derivatives were synthesized by reacting with coumarin moiety and studied for their antibacterial and antifungal activities. The synthesis of compounds (6a-9c) was achieved through the versatile and efficient synthetic route that involved reaction of thiazolidinedione with appropriately α-bromo ketone or α-bromo oxime derivatives (2a, 5c). The structures of these compounds were established by means of IR, 1 H-NMR, 13 C-NMR Mass and elemental analysis.

show abstract

“…In addition, the resonance appeared in the range of δ 6.71-8.05 ppm as singlets, doublets, triplets and multiplates are attributed to the aromatic protons. The piperazine protons were resonated as multipletes at δ 2.60-3.67 ppm [25]. The dioxane ring protons were resonated in the region δ 4.11-5.22 ppm.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives

Mallesha

Mohana

2011

Eur. J. Chem.

View full text Add to dashboard Cite

Synthesis and antibacterial activity of N-[2-(2-naphthyl)ethyl]piperazinyl quinolones

Cited by 10 publications

References 20 publications

N-substituted piperazinyl sarafloxacin derivatives: synthesis and in vitro antibacterial evaluation

N-substituted piperazinyl sarafloxacin derivatives: synthesis and in vitro antibacterial evaluation

Synthesis and Characterization of Some New Thiazolidinedione Derivatives Containing a Coumarin Moiety for their Antibacterial and Antifungal Activities

Synthesis, antimicrobial and antioxidant activities of 1-(1,4-benzodioxane-2-carbonyl)piperazine derivatives

Contact Info

Product

Resources

About