Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety

Wang, Shuo; Jia, Xuedong; Liu, Mingliang; Lu, Yu; Guo, Hai‐Ming

doi:10.1016/j.bmcl.2012.07.040

Cited by 40 publications

(16 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…42−44 Further modulation of hydrophilic/lipophilic balance can be achieved by introducing different substituents to the distant N atom on the piperazine ring. 45 …”

Section: Introductionmentioning

confidence: 99%

Effect of the Piperazine Unit and Metal-Binding Site Position on the Solubility and Anti-Proliferative Activity of Ruthenium(II)- and Osmium(II)- Arene Complexes of Isomeric Indolo[3,2-c]quinoline—Piperazine Hybrids

et al. 2014

View full text Add to dashboard Cite

In this study, the indoloquinoline backbone and piperazine were combined to prepare indoloquinoline–piperazine hybrids and their ruthenium- and osmium-arene complexes in an effort to generate novel antitumor agents with improved aqueous solubility. In addition, the position of the metal-binding unit was varied, and the effect of these structural alterations on the aqueous solubility and antiproliferative activity of their ruthenium- and osmium-arene complexes was studied. The indoloquinoline–piperazine hybrids L1–3 were prepared in situ and isolated as six ruthenium and osmium complexes [(η6-p-cymene)M(L1–3)Cl]Cl, where L1 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo[3,2-c]quinolin-2-N-amine, M = Ru ([1a]Cl), Os ([1b]Cl), L2 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo[3,2-c]quinolin-4-N-amine, M = Ru ([2a]Cl), Os ([2b]Cl), L3 = 6-(4-methylpiperazin-1-yl)-N-(pyridin-2-yl-methylene)-11H-indolo[3,2-c]quinolin-8-N-amine, M = Ru ([3a]Cl), Os ([3b]Cl). The compounds were characterized by elemental analysis, one- and two-dimensional NMR spectroscopy, ESI mass spectrometry, IR and UV–vis spectroscopy, and single-crystal X-ray diffraction. The antiproliferative activity of the isomeric ruthenium and osmium complexes [1a,b]Cl–[3a,b]Cl was examined in vitro and showed the importance of the position of the metal-binding site for their cytotoxicity. Those complexes containing the metal-binding site located at the position 4 of the indoloquinoline scaffold ([2a]Cl and [2b]Cl) demonstrated the most potent antiproliferative activity. The results provide important insight into the structure–activity relationships of ruthenium- and osmium-arene complexes with indoloquinoline–piperazine hybrid ligands. These studies can be further utilized for the design and development of more potent chemotherapeutic agents.

show abstract

“…42−44 Further modulation of hydrophilic/lipophilic balance can be achieved by introducing different substituents to the distant N atom on the piperazine ring. 45 …”

Section: Introductionmentioning

confidence: 99%

Effect of the Piperazine Unit and Metal-Binding Site Position on the Solubility and Anti-Proliferative Activity of Ruthenium(II)- and Osmium(II)- Arene Complexes of Isomeric Indolo[3,2-c]quinoline—Piperazine Hybrids

et al. 2014

View full text Add to dashboard Cite

show abstract

“…In another study, 19 the ciprofloxacin derivative containing an N-chlorosubstituted phenylethyl residue was found to be more effective against gram-positive and gram-negative bacteria than the quinolone group reference drugs. Wang et al 20 demonstrated that new ciprofloxacin derivatives have 21 that some of the quinolone hydrazide derivatives and standard drugs like ciprofloxacin and ampicillin have similar antimicrobial activity. Also, aminothiazolyl norfloxacin analogs synthesized by Wang et al 22 demonstrated more efficient antimicrobial activity against K. pneumoniae and C. albicans than chloromycin and ciprofloxacin.…”

Section: Discussionmentioning

confidence: 99%

Investigation of Antimicrobial and Anti-Quorum Sensing Properties of Some Derivatives of Cephalosporanic Acid, Ciprofloxacin, Norfloxacin, and Penicillanic Acid

Hamidi

Tüfekci

Demirbaş

et al. 2020

Kocaeli Üniversitesi Sağlık Bilimleri Dergisi

View full text Add to dashboard Cite

Objective: The rapid increase of antibiotic resistance among bacteria is a serious public health problem. Studies have focused on the di scovery of new antibiotic molecules and the development of new therapeutic strategies to combat these resistant bacteria. Once it was known that pathogenic bacteria regulate synthesis of virulence factors by the quorum sensing (QS) mechanism, QS inhibition became an attractive tar get for antibacterial treatment. This study aimed to investigate the antimicrobial activities and anti-QS properties of 16 derivatives of cephalosporanic acid, ciprofloxacin, norfloxacin, and penicillanic acid. Methods: Antimicrobial activity of the derivatives was tested by the agar well diffusion method against various microorganisms. The mi nimum inhibitory concentration (MIC) of effective derivatives was assessed by the broth microdilution method. Anti-QS properties were investigated using the soft agar method, observing inhibition of violacein production in Chromobacterium violaceum. The data were compared statistically. Results: Six norfloxacin derivatives displayed antimicrobial activity against a number of organisms, three of which were more effective than control antibiotics (p<0.05) against some organisms. One ciprofloxacin derivative demonstrated antimicrobial activity against all tested bacteria and was more effective against some bacteria than control antibiotic (p<0.05). The MIC values of these six norfloxacin and one ciprofloxacin derivatives were between 0.04-6.25 µg/mL and 0.04-3.12 µg/mL, respectively. A cephalosporanic acid and a penicillanic acid derivative displayed anti-QS properties. Conclusion: This study shows that some new derivatives of cephalosporanic acid, ciprofloxacin, norfloxacin, and penicillanic acid may have potential for development of new antibacterial and anti-QS agents.

show abstract

“…The piperazine moiety has privileged position in medicinal chemistry with diverse biological activities [24] . Bisarylpiperazine derivatives exhibited activities such as anti-leishmanial [25] , anti-microbial [24] , [26] , [27] , anti-protozoal [28] , [29] , anti-cancer [30] , anti-tubercular [30] , [31] and anti-viral [32] ( Fig. 1 ).…”

Section: Introductionmentioning

confidence: 99%

Biological evaluation and structure activity relationship of 9-methyl-1-phenyl-9H-pyrido[3,4-b]indole derivatives as anti-leishmanial agents

Ashok

Chander

Smith

et al. 2019

Bioorganic Chemistry

View full text Add to dashboard Cite

show abstract

Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety

Cited by 40 publications

References 26 publications

Effect of the Piperazine Unit and Metal-Binding Site Position on the Solubility and Anti-Proliferative Activity of Ruthenium(II)- and Osmium(II)- Arene Complexes of Isomeric Indolo[3,2-c]quinoline—Piperazine Hybrids

Effect of the Piperazine Unit and Metal-Binding Site Position on the Solubility and Anti-Proliferative Activity of Ruthenium(II)- and Osmium(II)- Arene Complexes of Isomeric Indolo[3,2-c]quinoline—Piperazine Hybrids

Investigation of Antimicrobial and Anti-Quorum Sensing Properties of Some Derivatives of Cephalosporanic Acid, Ciprofloxacin, Norfloxacin, and Penicillanic Acid

Biological evaluation and structure activity relationship of 9-methyl-1-phenyl-9H-pyrido[3,4-b]indole derivatives as anti-leishmanial agents

Contact Info

Product

Resources

About