Synthesis and antibacterial activity of N-[2-(5-bromothiophen-2-yl)-2-oxoethyl] and N-[(2-5-bromothiophen-2-yl)-2-oximinoethyl] derivatives of piperazinyl quinolones

Foroumadi, Alireza; Emami, Saeed; Mehni, Massood; Moshafi, Mohammad Hassan; Shafiee, Abbas

doi:10.1016/j.bmcl.2005.07.005

Cited by 71 publications

(32 citation statements)

References 18 publications

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“…Similarly, the O-methyloxime ethers 8b and O-benzyloxime ethers 8c were synthesized by reaction of compound 7 with methoxyamine hydrochloride and O-benzylhydroxylamine hydrochloride, respectively. [10][11][12] Reaction of 7-piperazinylquinolones (1, 2 or 3) with 3-(bromoacetyl)thiophene 7 or a-bromooxime derivatives 8a-c in DMF, in the presence of NaHCO 3 at room temperature afforded corresponding ketones 5a-c and oxime derivatives 5d-l, respectively. [10][11][12] Accordingly, enoxacin 3 and ciprofloxacin 2 reacted with abromooxime 8a to give exclusively (E)-5d and (E)-5f.…”

Section: Resultsmentioning

confidence: 99%

“…1) solely by the linkage of various 2-(thiophen-2-yl)ethyl groups to the piperazinyl residue at C-7 of the parent drug and explored their antibacterial activities. [10][11][12] By considering the considerable activity of N- [2-(thiophen-2-yl)ethyl] piperazinyl quinolone derivatives 4 against Gram-negative and Grampositive bacteria, a new series of N- [2-(thiophen-3-yl)ethyl] derivatives of piperazinyl quinolone (5, Fig. 1) were also synthesized and evaluated for antibacterial activity as positional isomers of 4.…”

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confidence: 99%

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Synthesis and Antibacterial Activity of New N-[2-(Thiophen-3-yl)ethyl] Piperazinyl Quinolones

Letafat

Emami

Mohammadhosseini

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Synthesis and Antibacterial Activity of New N-[2-(Thiophen-3-yl)ethyl] Piperazinyl Quinolones

Letafat

Emami

Mohammadhosseini

et al. 2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Yields are of purified products and were not optimized. NOR (1), CIPRO (2) and PI-PEM (3) were purchased from Fluka (SigmaAldrich ChemieGmbh Munich, Germany). [(Benzoylamino) methyl]triethylammonium salts 4a-d were prepared as [(3-chlorobenzoylamino) methyl] triethylammonium chloride, as reported in BreznicaSelmani et al [19].…”

Section: Methodsmentioning

confidence: 99%

“…The SAR studies revealed that the fluorine atom and the 1-alkyl, 1,4-dihydro-4-oxo-quinolone-3-carboxylic acid skeleton of fluoroquinolone are responsible for potency, represented in binding not only to DNA gyrase, but also to type-II-isomerase and topoisomerase IV [2]. The quinolones were further enhanced by the addition of corresponding groups to the N-1, C-5 and C-7 positions of their respective basic molecule.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

Breznica-Selmani

Mladenovska

Dräger

et al. 2016

Maced. J. Chem. Chem. Eng.

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Herein we report the synthesis of different derivatives of (fluoro)quinolones norfloxacin, ciprofloxacin and pipemidic acid, by incorporating (benzoylamino)methyl on the free nitrogen of the pyperazinyl moiety. The compounds were structurally characterized by 1D and 2D NMR, FTIR and highresolution mass spectroscopy. In addition, their physicochemical properties were a matter of interest to be correlated with their structure and antimicrobial activity in vitro. Their antimicrobial activities were screened against Gram-positive, Gram-negative bacteria and C. albicans. Higher distribution coefficients and consequently lower water solubility were determined for all synthesized compounds than the ones of the corresponding leading compounds. Inconsequential correlations between the lipophilicity of the compounds and MIC were observed, suggesting that passive diffusion is not the only mechanism for their penetration into bacterial cells. Further studies are needed to determine how substitutions in the (fluoro)quinolone moiety affect the primary target(s), substrate behavior in respect to bacterial transporters and overall bioavailability.Keywords: (benzoylamino)methyl; quinolones; structure; physicochemical properties; antimicrobial activity СИНТЕЗА, ФИЗИЧКОХЕМИСКА КАРАКТЕРИЗАЦИЈА И АНТИБАКТЕРИСКА АКТИВНОСТ НА НОВИ (БЕНЗОИЛАМИНО)МЕТИЛНИ ДЕРИВАТИ НА ХИНОЛОНИВо трудот е прикажана синтеза на различни деривати на (флуоро)хинолони со инкорпорирање на (бензоиламино)метилна група на слободниот азот од пиперазинскиот фрагмент кај норфлоксацинот, ципрофлоксацинот и пипемидинската киселина како водечки соединенија. Синтетизираните соединенија беа структурно карактеризирани со помош на 1D и 2D NMR, FTIR и масена спектрометрија со висока резолуција. Дополнително беа определени физичкохемиските особини на новосинтетизираните соединенија и корелирани со нивната структура и антимикро- 179-197 (2016) 180 бната активност in vitro. Антимикробната активност на новите соединенија беше испитувана на Gram-позитивни и Gram-негативни бактерии и на C. albicans. Сите новосинтетизирани соеди-ненија покажаа повисок коефициент на распределба и соодветно пониска растворливост во вода во однос на водечките соединенија. Корелациите меѓу липофилноста на синтетизираните соединенија и минималната инхибиторна концентрација (MIC) не беа статистички значајни, што укажува на тоа дека пасивната дифузија не е единствениот механизам со кој тие пенетрираат во бактериските клетки. Потребни се понатамошни истражувања за да се испита како супституциите во (флуоро)хинолонското јадро влијаат врз примарната цел(и), супстратното однесување во однос на бактериските транспортери и севкупната биорасположливост.

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“…Imidazole derivatives are found to have diverse activities, such as anti-inflammatory, antimicrobial (Divya et al, 2013), antibacterial, anticancer, antifungal, analgesic, anti-HIV and antituberculosis (Verma et al, 2013). The presence of a 5-bromothiophen-2-yl unit is found to enhance the antibacterial activity of piperazinyl quinolones (Foroumadi et al, 2005) and antimicrobial activity in pyrazoline derivatives (Sasikala et al, 2012).…”

Section: Structure Descriptionmentioning

confidence: 99%

2-(5-Bromothiophen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

Kavitha¹,

Mayakrishnan

Perumal

et al. 2017

IUCr Data

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In the title molecule, C25H15BrN2S, the phenanthrene system is slightly skewed, with a dihedral angle of 8.94 (16)° between the outer benzene rings. The imidazole ring makes dihedral angles of 15.18 (16), 2.94 (15) and 88.46 (16)°, respectively, with the thiophene ring, the central benzene ring of the phenanthrene unit and the phenyl ring attached to the latter unit. In the molecule, there are two C—H...π interactions present involving the phenyl ring. In the crystal, molecules are linked by C—H...N and C—H...Br hydrogen bonds, forming zigzag chains along theaaxis. The chains are linked by C—H...π interactions, forming a three-dimensional supramolecular structure.

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Synthesis and antibacterial activity of N-[2-(5-bromothiophen-2-yl)-2-oxoethyl] and N-[(2-5-bromothiophen-2-yl)-2-oximinoethyl] derivatives of piperazinyl quinolones

Cited by 71 publications

References 18 publications

Synthesis and Antibacterial Activity of New N-[2-(Thiophen-3-yl)ethyl] Piperazinyl Quinolones

Synthesis and Antibacterial Activity of New N-[2-(Thiophen-3-yl)ethyl] Piperazinyl Quinolones

Synthesis, physicochemical characterization and antibacterial activity of novel (benzoylamino)methyl derivatives of quinolones

2-(5-Bromothiophen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

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