Synthesis and Antibacterial Activity of New 7‐Piperazinyl‐quinolones Containing a Functionalized 2‐(Furan‐3‐yl)ethyl Moiety

Foroumadi, Alireza; Mohammadhosseini, Negar; Emami, Saeed; Letafat, Bahram; Faramarzi, Mohammad Ali; Samadi, Nasrin; Shafiee, Abbas

doi:10.1002/ardp.200600169

Cited by 25 publications

(11 citation statements)

References 20 publications

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“…The introduction of the following 4,5,6-membered nitrogencontaining heterocycles is favorable: piperazinyl [3], bicycles [13,97], pyrrolidinyl, piperidinyl [55,60,112], piperazinyl [60]. They, in turn, can contain various bulky substituents (2-(2-furyl)-and 2-(3-thienyl)-2-oxoethyl, hydroxyiminoethyl [102,116], 1,3,4-thiadiazol-2-yl [103][104][105]). Compounds with cyclopropyl, 1-aminocyclopropyl, vinyl, aminomethyl [80], and amino-tert-butyl [64] substituents exhibit excellent activity [13].…”

Section: Methodsmentioning

confidence: 99%

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

107

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Data on methods for the construction of the 4-quinolone skeleton and modification of the substituents around it are reviewed. The "structure-activity" relationships of 4-quinolones are examined with respect to antibacterial and antitumor activity.Keywords: 4-quinolones, biological activity. 4-Quinolones have been a subject of research for many scientific teams, and this is reflected in the numerous reviews and monographs devoted to various aspects of the subject. One of the early reviews [1] concerns aspects of the synthesis of individual representatives of the group of 4-quinolones and comparative characterization of their antimicrobial activity. Basic approaches to construction of the fluoroquinolone skeleton and also variation of the substituents at various positions of the ring were examined in the review [2]. The relationship between the structure and antibacterial activity is discussed in [3], and methods for the synthesis of polycyclic derivatives of 4-quinolones based on the annelation of rings to the various faces of the quinoline skeleton are discussed in the review [4]. The reviews [5, 6] were devoted to identification of the structural modifications of 4-quinolones responsible for their conversion from antibacterial agents to antitumor agents. The molecular and biological aspects of the antibacterial action of 4-quinolone-3-carboxylic acids are examined in [7], and issues concerned with the clinical application of 4-quinolones are discussed in the reviews [8][9][10][11][12] and in the monograph [13]. The synthesis and the "structure-activity" relationships of the bioisosteres of 4-quinolones -2-pyridones -are examined in the review [14].The aim of the present review was to classify existing methods for the synthesis not only of fluoroquinolones but also of any 4-quinolones, to demonstrate the effects of modification of the molecule at all positions, to summarize data on the various types of activity, and to examine the "structure-activity" relationship with respect to antibacterial and antitumor activity.

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Section: Methodsmentioning

confidence: 99%

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

107

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“…1 H-NMR spectroscopy is generally used to assign the (E)-and (Z)-geometry of oximes [20,21]. Surveying similar oximes (chroman-4-one oxime systems) suggests that the proximity of the C-5 proton to the oxygen of the oxime in the a-syn configuration will deshield the proton [22,23].…”

Section: Chemistrymentioning

confidence: 99%

Conformationally Constrained Analogs of N‐Substituted Piperazinylquinolones: Synthesis and Antibacterial Activity of N‐(2,3‐Dihydro‐4‐hydroxyimino‐4H‐1‐benzopyran‐3‐yl)‐piperazinylquinolones

Emami

Foroumadi

Samadi

et al. 2009

Archiv der Pharmazie

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A series of novel quinolone agents bearing a particular bulky and conformationally constrained bicyclic substituent (2,3-dihydro-4-hydroxyimino-4H-1-benzopyran-3-yl- moiety) on the piperazine ring of 7-piperazinyl quinolones (norfloxacin, enoxacin, ciprofloxacin, and levofloxacin) were synthesized and evaluated against a panel of Gram-positive and Gram-negative bacteria. Among these derivatives, ciprofloxacin counterpart 9c, highly inhibited the tested Gram-positive bacteria, superior to that of the reference drugs, and displayed antibacterial activity at non-cytotoxic concentrations.

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“…have found widespread use [124][125][126]. Derivatives of the oximes of pyridazine [127,128], pyrazine [129], quinoxaline [130,131], piperazine [132][133][134][135][136][137][138][139][140][141], 1,2,4-triazine [142,143], 1,4-oxathiane [144], and 1,3,4-thiadiazine [145] also exhibit high antibacterial activity.…”

Section: Bactericidal Anticancer and Antiviral Activitymentioning

confidence: 99%

Oximes of six-membered heterocyclic compounds with two and three heteroatoms. II.* Reactions and biological activity (review)

Абеле

Golomba

et al. 2010

Chem Heterocycl Comp

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Data on the reactions of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes and their derivatives are reviewed. The synthesis of new heterocycles based on the oximes of six-membered heterocyclic compounds with two and three heteroatoms is considered separately. The principal results of research into the biological activity of these oximes and their ethers are also presented.The oximes of six-membered heterocyclic compounds with two and three heteroatoms are widely used as intermediates in fine organic synthesis. Their production methods and structural features were examined in the review [1]. In this article we discuss the reactions of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes and their derivatives. Methods for the synthesis of new heterocyclic systems from the derivatives of these oximes are considered in a separate section. In the last section some results from investigation of the biological activity of the ethers of these oximes are considered.

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Synthesis and Antibacterial Activity of New 7‐Piperazinyl‐quinolones Containing a Functionalized 2‐(Furan‐3‐yl)ethyl Moiety

Cited by 25 publications

References 20 publications

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Conformationally Constrained Analogs of N‐Substituted Piperazinylquinolones: Synthesis and Antibacterial Activity of N‐(2,3‐Dihydro‐4‐hydroxyimino‐4H‐1‐benzopyran‐3‐yl)‐piperazinylquinolones

Oximes of six-membered heterocyclic compounds with two and three heteroatoms. II.* Reactions and biological activity (review)

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