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Synthesis And Anti-mycobacterial Activities Of Triazoloquinolones.
A. Carta, M. Palomba, I. Briguglio, P. Corona, S. Piras, D. Jabés, Paola Guglierame, P. Molicotti, S. Zanetti
Published 2011 · Chemistry, Medicine
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A number of quinolone derivatives have been reported to possess anti-mycobacterial activity. Generally. Mycobacterium tuberculosis isolates expressing resistance to both isoniazid and rifampin are susceptible to fluoroquinolones. Benzotriazole is a hetero-bicyclic aromatic ring endowed with interesting chemical and biological properties and pharmacological activities. In a preliminary study we have recently reported the activity of triazolo[4,5-h]quinolone-carboxylic acids, a new class of benzotriazole derivatives active against multi-drug resistant M. tuberculosis (MDR-Mtb). In this study we confirm that this novel class of quinolones is endowed with a selective anti-mycobacterial activity, coupled with absence of cytotoxicity. The SAR analysis of the new derivatives in comparison with the previous series shows that the methyl group is the most effective substituent in both N-3 and N-9 positions of the ring system.
This paper references
Activity and molecular modeling of a new small molecule active against NNRTI-resistant HIV-1 mutants.
A. Carta (2009)
Synthesis and antiproliferative activity of 3-aryl-2-(1H-benzotriazol-1-yl)acrylonitriles. Part III.
A. Carta (2002)
1,2,3-triazolo[4,5-h]quinolines. III. Preparation and antimicrobial evaluation of 4-ethyl-4,7-dihydro-1(2)-R-1(2)H triazolo[4,5-h]quinolin-7-one-6-carboxylic acids as anti-infectives of the urinary tract.
P. Sanna (1992)
[1,2,3]Triazolo[4,5-h]quinolones. A new class of potent antitubercular agents against multidrug resistant Mycobacterium tuberculosis strains.
A. Carta (2007)
Synthesis of Two Novel Tricyclic Rings:Triazolo[4,5-g]quinolines and Pyrido[2,3-g]quinoxalines Derived from 6,7-Diaminoquinolines
P. Sanna (2000)
A novel addition–rearrangement of O-(1-benzotriazolylalkyl)oximes with organolithium reagents. Convenient non-oxidative conversions of aldehydes into amides
A. R. Katritzky (1992)
Anti-Mycobacterial Activity of Quinolones. Triazoloquinolones a New Class of Potent Anti-Mycobacterial Agents
A. Carta (2008)
[Preparation and pharmacologic activity of N-oxides of 4'-(benzotriazol-2-yl-phenylalkanoic and -phenoxyalkanoic acids].
A. Boido (1989)
Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)-benzotriazol-1(2)-yl]acrylonitriles variously substituted: Part 4.
A. Carta (2004)
Synthesis of substituted DL-3(5-benzazolyl)alanines as dopa and alpha-methyldopa analogs and their effects on dopamine beta-hydroxylase, tyrosinase and diphenoloxidase.
M. Loriga (1992)
A New synthesis of triazolo[4,5-g]quinolines and unexpected ring reduced products by treatment with hydrazine hydrate
A. Carta (2004)
Reactions of benzotriazoles with diethyl ethoxymethylenemalonate; ethylation and michael addition. Comparison with other esters and N-heterocycles
P. Sanna (1997)
305. Quinoline compounds containing arsenic. Part V. Synthesis of 7 : 8-triazolquinoline-5-arsonic acid
R. H. Slater (1932)
Synthesis and antimycobacterial activity of 3-aryl-, 3-cyclohexyl- and 3-heteroaryl- substituted-2-(1H(2H)-benzotriazol-1(2)-yl)prop-2-enenitriles, prop-2-enamides and propenoic acids. II.
P. Sanna (2002)
Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically : approved standard
M. Ferraro (2000)
Synthesis and antitubercular activity of 3-aryl substituted-2-[1H(2H)benzotriazol-1(2)-yl]acrylonitriles.
P. Sanna (2000)
Synthesis and Biological Evaluation of Triazolo[4,5- g ]quinolines, Imidazo[4,5- g ]quinolines and Pyrido[2,3- g ]quinoxaline. Part II
A. Carta (2003)
13C-NMR as useful tool for unambiguous identification of ring substituted N1(2)(3)-alkylbenzotriazole isomers
A. Carta (2001)
Synthesis and characterization of some N-Mannich bases of [1,2,3]triazoloquinolines
M. Ferlin (2002)
Triazolo[4,5-f]quinolines Derived from 5-Amino-(1H- and 2-methyl-2H)-benzotriazoles with b-Diketones and 3-Buten-2-one
P. Sanna (1999)
Untersuchungen in der Reihe des Azimidobenzols und des N-Methyl-azimidobenzols
K. Fries (1934)
Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds.
R. Pauwels (1988)
Preparation and local anaesthetic activity of N-[2-(tert-amino)ethyl]- and N-(lupinyl)-benzotriazol-1/2-ylacetamides.
I. Vazzana (1997)
Structural Elucidation of Isomeric Methyl (E)-3-[5-Aminobenzotriazol-1(2)(3)-yl]propenoates by NMR Spectroscopy
A. Carta (1997)
Synthesis of E/Z 3-(1H-Benzotriazol-1-yl)-3-(pyridin-4-yl)acrylonitriles and E/Z 2-(3-Imino-2-benzofuran-1(3H)-ylidene)acetonitriles. An Unusual Case of Displacement of the Benzotriazole Ring
A. Carta (2002)
Benzotriazole: A novel synthetic auxiliary
A. Katritzky (1991)
Triazolo[4,5-f]quinolines. Part VI. Synthesis and evaluation of 9-aminoalkyl(aryl)-2-methyl-2H-[4,5-f]quinolines as anticancer agents. Preliminary results of in vitro screening.
P. Sanna (1995)
Choleretic activity of 3-[ring substituted benzotriazol-1(2)-yl]alkanoic and alkenoic acids.
G. Paglietti (1994)
This paper is referenced by
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A. Kumar (2015)
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Anilkumar Ambala (2020)
Quinolone–Triazole Hybrids and their Biological Activities
J. Xu (2018)
Drug development pipeline for the treatment of tuberculosis : Needs , challenges , success and opportunities for the future
N. Anand (2015)
Making endo-cyclizations favorable again: a conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides.
A. A. Ageshina (2019)
Design, synthesis and antimicrobial activities of 1,2,3-triazole derivatives
X. Zhao (2012)
Molecular iodine catalyzed synthesis of tetrazolo[1,5-a]-quinoline based imidazoles as a new class of antimicrobial and antituberculosis agents
Divyesh C. Mungra (2012)
Mannich bases of 7-piperazinylquinolones and kojic acid derivatives: synthesis, in vitro antibacterial activity and in silico study.
S. Emami (2013)
Pharmacophore insights into rpoB gene mutations in Mycobacterium tuberculosis rifampicin resistant isolates.
R. Figueiredo (2012)
In vitro evaluation of new 2-phenoxy-benzo[g][1,2,4]triazolo[1,5-a]quinazoline derivatives as antimicrobial agents.
Hatem A. Abuelizz (2018)
A Brief Overview on Recent Advances in the Development of Anti-Tubercular Compounds Containing Different Heterocyclic Ring Systems
M. Asif (2016)
Synthèse et activité antituberculeuse de quelques dérivés de la 1,10-phénanthrolinone
Songuigama Coulibaly (2018)
Synthesis and Antimicrobial Activities of Novel Aminoalkylated 2H-benzotriazoles
Bharti Bhardwaj (2014)
Application of 9-ethyl[1,2,5]selenadiazolo[3,4-h]quinolones in the synthesis of tricyclic azoloquinolones
M. Bella (2014)
Design, synthesis and antitubercular activity of 4-alkoxy-triazoloquinolones able to inhibit the M. tuberculosis DNA gyrase.
A. Carta (2019)
Benzotriazole: An overview on its versatile biological behavior
I. Briguglio (2015)
An overview of new antitubercular drugs, drug candidates, and their targets
Aparna Bahuguna (2019)
Fluoroquinolone derivatives and their anti-tubercular activities.
Yi-lei Fan (2018)
Recent Advances on Diversity Oriented Heterocycle Synthesis of Fused Quinolines and Its Biological Evaluation
Mohamed Abass (2020)
Quinoline and quinolones: promising scaffolds for future antimycobacterial agents
S. Singh (2015)
Quinoline Derivatives with Potential Activity Against Multidrug‐resistant Tuberculosis
Bi Liu (2018)