Synthesis of 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives as potential antimicrobial agents

Rameshkumar, Natesh; Ashokkumar, Mohan; Subramanian, Ekambaram Harihara; Ilavarasan, R.; Sridhar, S.

doi:10.1016/s0223-5234(03)00151-x

Cited by 40 publications

(20 citation statements)

References 12 publications

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“…The minimal inhibitory concentration (MIC in lg/mL) was determined (Table 1) using an adaptation of agar streak dilution method based on radial diffusion. 9,10 Suspensions of the microorganism were prepared to contain approximately 10 8 cfu/mL and the plates were inoculated. A stock solution of the synthesized compound (1000 lg/mL) in DMSO was prepared and graded dilutions of the tested compounds were incorporated in a cavity (depth 3 mm, diameter 4 mm) made in the center of the petridish (nutrient agar for antibacterial activity and sabouraud dextrose agar medium for antifungal activity).…”

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confidence: 99%

Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Ferreira

Calhelha

Estevinho

et al. 2004

Bioorganic & Medicinal Chemistry Letters

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Abstract-Gram positive (Bacillus cereus, B. subtilis), Gram negative (Pseudomonas aeruginosa, Escherichia coli) bacteria, and Candida albicans as a representative of fungi were used for screening the in vitro antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo [b]thiophene series bearing different substituents, synthesized by us using the palladium-catalyzed C-N coupling methodology. The minimal inhibitory concentration (MIC) and structure-activity relationships (SARs) were evaluated. Ó 2004 Elsevier Ltd. All rights reserved.The enhance prevalence of infectious diseases is becoming a world wide problem. Additionally, the resistance problem demands that a renewed effort should be made to seek antimicrobial agents effective against pathogenic microorganisms resistant to current treatment. Benzo[b]thiophenes are important heterocycles as biological active molecules. 1-5 Recently we have been interested in the palladium-catalyzed aryl amination of benzo [b]thiophenes either in the benzene or in the thiophene ring to obtain the corresponding diarylamines and in some cases the tetracyclic aromatic compounds resulting from intramolecular cyclizations. 6,7 We have been able to establish that under the same C-N coupling conditions [Pd(OAc) 2 (3 mol %), Cs 2 CO 3 (1.4 equiv), and BINAP (4 mol %) in toluene] it was possible to obtain either primary amines 8 or diarylamines 7,8 in the benzene ring of the benzo[b]thiophene moiety.Herein, we describe the structure-activity relationship of a novel series of diarylamines as antimicrobial agents. Differently substituted diarylamines derivatives of 2,3,5-trimethylbenzo[b]thiophene 1 were obtained by C-N palladium-catalyzed cross-couplings in good to high yields (50%-quantitative yield) using either the bromo compound 2 or the amino derivative 3 as coupling components. 8 The latter was prepared from compound 2 using also a C-N palladium-catalyzed cross-coupling with benzophenone imine, followed by acidic hydrolysis in a 60% overall yield (Scheme 1). 8 A screening of antibacterial activities using two Gram negative (Escherichia coli and Pseudomonas aeruginosa) and two Gram positive bacteria (Bacillus subtilis and B. cereus) and antifungal using Candida albicans was performed for the diarylamines 4-8 and for their benzo[b]thiophene precursors 1-3, to determine the importance of the diarylamine skeleton in this series. The minimal inhibitory concentration (MIC in lg/mL) was determined (Table 1) using an adaptation of agar streak dilution method based on radial diffusion. 9,10 Suspensions of the microorganism were prepared to contain approximately 10 8 cfu/mL and the plates were inoculated. A stock solution of the synthesized compound (1000 lg/mL) in DMSO was prepared and graded dilutions of the tested compounds were incorporated in a cavity (depth 3 mm, diameter 4 mm) made in the center of the petridish (nutrient agar for antibacterial activity and sabouraud dextrose agar medium for antifungal activity). The plates were incubated at 37°C (bacteria) or 30°C (fungi) for ...

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confidence: 99%

Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Ferreira

Calhelha

Estevinho

et al. 2004

Bioorganic & Medicinal Chemistry Letters

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“…Receptor Grid Generation program was used to prepare 4BMO Grid and all ligands were optimized by LigPrep program by using OPLS-2005 force field to generate lowest energy state of ligands. (7)(8)(9)(10)(11)(12) Piperdin-4-one (0.01 mol) and triethylamine (0.01 mol) in 30 mL of dry benzene, benzoylchloride (0.01 mol) in 20 mL of benzene was added dropwise through the separating funnel for about half an hour. Stirring was continued with (0˚C) a magnetic stirrer.…”

Section: Ligand Structure Preparationmentioning

confidence: 99%

“…Piperidin-4-one nucleus are interested to study because of their broad spectrum of biological activities such as antibacterial and antifungal [2][3] local anesthetic [4] antiviral [5] antitumor [6]. The utility of substituent's at second, third and sixth positions, particularly aromatic substituent at second and/or sixth positions with regard to its biological activity have well documented by many workers [7][8]. Hydrazone derivatives have been claimed to exhibit appreciable antimicrobial [9][10][11][12] antitubercular [13] anticonvulsant [14] antiviral [15] and anti-inflammatory [16] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation and Docking Studies of some Novel (E)-(4-(2-(Benzo[d]Thiazol-2-yl)Hydrazono)Methyl-2,6-Diphenylpiperidin-1-yl)(Phenyl)Methanone Derivatives

Rajaraman

Sundararajan

Krishnasamy

2015

ILCPA

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ABSTRACT.A series of biologically active some novel (E)-(4-(2-(benzo [d] thiazol-2-yl)hydrazono)-3-methyl-2,6-diphenylpiperidin-1-yl)(phenyl)methanone derivatives (14-19) were synthesized and characterized by IR, 1 H NMR, 13C NMR and HSQC spectral analysis. Molecular docking studies were also carried out for compounds 14-19 using the crystal structure of Ribonucleotide Reductase to disclose the binding mode and orientation of target molecule into the active site of respective receptors. The synthesized compounds were also screened for their antimicrobial activity against selected panel strains Antimicrobial studies revealed that the synthesized compound 14 exhibited noticeable activity against B.cerus whereas compounds17 and 18 displayed appreciable activity against K.pneumoniae. Bromo substituted phenyl group at C-2 and C-6 of piperidine ring showed excellent antibacterial activity against K.pneumoniae and B.cerus at MIC of 25μg/ml. The antifungal studies revealed that compounds 17, 18 and 19 exposed significant antifungal activity against the pathogenic strains used in this study. In particular compound 19 are showed excellent antifungal activity against C.albicans and A.niger.

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“…Further growth was arrested by the addition of lactophenol aniline blue to each of the wells. The minimal inhibitory concentration (MIC, in mg mL -1 ) was determined using an adaptation of the agar streak dilution method based on radial diffusion (9,10). Under the same conditions, ampicillin (antibacterial) and cycloheximide (antifungal) were used as standards.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Synthesis of progesterone heterocyclic derivatives of potential antimicrobial activity

Mohareb

Hana²

2008

Acta Pharmaceutica

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Progesterone is one of the most important hormones of the steroidal pregnane series, secreted by corpus luteum and by placenta, which can be regarded as a hormonal balancer, particularly of estrogens. It also helps to create a balance of all other steroids and has intrinsic calming and diuretic properties. It is important in women and its importance in men for the maintenance of prostate health is appreciated. Moreover, progesterone has a neuroprotective effect (1, 2). Thus, due to the importance of progesterones to the human body and in continuation of our previous work on heterocyclic synthesis (3-5), we would like to report here on the formation and characterization of new promising steroidal heterocyclic derivatives derived from progesterone. Detection of many emerging chemicals of concern, including antimicrobials and steroid hormones, in the environment was increased in the past decade with the advancement of analytical techniques. All compounds produced in this work are novel and their synthetic pathways are also novel. Therefore, the in vitro antimicrobial activity of the new steroidal derivatives should be tested against Gram positive and negative bacteria, and fungi. The aim of this work was to synthesize steroidal heterocycles and to elucidate the potential role of these compounds as antimicrobial agents. The synthesis of steroidal heterocycles containing the pyrazole, isoxazole, thiazole, pyrane, pyridine, pyridazine, or benzopyrane ring attached to the pregnene nucleus is reported. Progesterone (1) reacts with dimethyl formamide dimethyl acetal to form enamine 2. Heterocyclization of 2 with hydrazines, hydroxylamine, glycine, ethyl acetoacetate or cyanomethylene afforded novel steroidal heterocyclic derivatives. The in vitro antimicrobial evaluation showed that all synthesized compounds show activity against the used strains of Gram positive bacteria and fungi.

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Synthesis of 6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid derivatives as potential antimicrobial agents

Cited by 40 publications

References 12 publications

Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study

Synthesis, Biological Evaluation and Docking Studies of some Novel (E)-(4-(2-(Benzo[d]Thiazol-2-yl)Hydrazono)Methyl-2,6-Diphenylpiperidin-1-yl)(Phenyl)Methanone Derivatives

Synthesis of progesterone heterocyclic derivatives of potential antimicrobial activity

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