Synthesis of variously substituted 1,8-naphthyridine derivatives and evaluation of their antimycobacterial activity

Badawneh, Muwaffag; Manera, Clementina; Mori, Claudio; Saccomanni, Giuseppe; Ferrarini, Pier Luigi

doi:10.1016/s0014-827x(02)01235-1

Cited by 17 publications

(10 citation statements)

References 10 publications

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“…Reaction of compound 4-methyl-(1H,3(2H))-benzo[b] [1,4]diazepin-2-one 1 [9] with POCl 3 gave 2-chloro-4methyl-3H-benzo[b] [1,4]diazepine 2 [10][11][12][13][14][15] (Scheme 1). The structure of 2 was established by IR, 1 H NMR, and mass spectra spectroscopic analysis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some New Benzo[b][1,4]diazepine Based Heterocycles

Azab

2013

Journal of Heterocyclic Chem

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Preparation of 4‐chloro‐3H‐benzo[b][1,4]diazepine‐2‐carbaldehyde 5, which is used as a key intermediate in the synthesis of chalcones derivatives, via its condensation with some aromatic acetophenone derivatives under ethanol piperidine condition was described. Also illustrated was the reaction of such chalcones with available nucleophilics and reagents of active methylene group to afford new series of fused and isolated pyrazoles, isoxazolines pyrimidines, pyridines, triazolo[1,5‐a]pyrimidines, benzo[1,4]oxa(thia)zepines, and pyrido[1,2‐a]benzimidazoles incorporating 4‐chloro‐3H‐benzo[b][1,4]diazepine moiety, which have a potential pharmaceutical interest. Furthermore, condensation reaction of 4‐chloro‐3H‐benzo[b][1,4]diazepine‐2‐carbaldehyde with aromatic amine derivatives to afford the Schiff's bases was described. The C═N double bond of the latter compounds has been reacted with chloroketene to give β‐lactams and with sulfanylacetic acid to give the 2‐(4‐oxo‐1,3‐thiazolidinyl)‐substituted derivative. The structures of the newly prepared compounds were established by elemental analysis, IR, MS, and 1H NMR spectral analysis.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Some New Benzo[b][1,4]diazepine Based Heterocycles

Azab

2013

Journal of Heterocyclic Chem

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“…These data were collected from the literature for the development of QSARs (Badawneh et al, 2002(Badawneh et al, , 2003. 6.25 lg/ml of compound was tested for antimycobacterial activity against M. tuberculosis H37Rv which is reported in terms of percentage inhibition.…”

Section: Methodsmentioning

confidence: 99%

QSAR studies on substituted 3- or 4-phenyl-1,8-naphthyridine derivatives as antimicrobial agents

2011

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Quantitative Structure Activity Relationship correlating the antitubercular and antibacterial (Staphylococcus aureus and Escherichia coli) activities with the structural descriptors of reported naphthyridine derivatives was developed. The data were divided into training and test sets. The former was used to develop the regression model and the latter was used to examine the predictive capability of these models. The statistical measures such as squared correlation coefficient (r 2 = 0.79-0.84), adjusted squared correlation coefficient (r 2 adj = 0.78-0.83) F-ratio (26.85-67.16), and cross-validation (q 2 = 0.74-0.79) were found to be satisfactory for all activities and the predictions were within the 99% confidence level. The models contained atom type, thermodynamic, structural, and electrotopological descriptors which emphasized the importance of the size, shape, and the lipophilicity of the molecule.

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“…The deriatives of 1,8-naphthyridine have been widely utilized in biochemistry and related fields. They can act as monodinucleating ligands (Gavrilova & Bosnich, 2004) for the preparation of multinuclear complexes, as molecular recognition receptors for urea, carboxylic acids and guanine (Goswami & Mukherjee, 1997;Nakatani et al, 2000), as medicines (Stuk et al, 2003;Ferrarini et al, 2004), and as antimycobacterial and antimicrobial agents (Badawneh et al, 2002;Badawneh et al, 2003). Recently, 1,8-naphthyridine derivatives have been reported to be excellent fluorescent markers of nucleic acids (Hoock et al, 1999) and probe molecules (Nakatani et al, 2001).…”

Section: Commentmentioning

confidence: 99%