Heterocyclic isosters of antimycobacterial salicylanilides

Matyk, Josef; Waisser, Karel; Drazkova, Katerina; Kuneš, Jiřı́; Klimešová, Věra; Palát, Karel; Kaustová, Jarmila

doi:10.1016/j.farmac.2005.02.002

Cited by 22 publications

(13 citation statements)

References 8 publications

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“…The development of new antituberculotic agents is the principal goal of our group. We have recently studied a number of structurally different compounds, such as the derivatives of pyridine [1,2], alkoxyphenylcarbamic acids [3], tetrazoles [4,5], dihydroindolethiones [6] and other heterocycles [7,8].…”

Section: Introductionmentioning

confidence: 99%

The Oriented Development of Antituberculotics: Salicylanilides

Waisser

Matyk

Divišová

et al. 2006

Archiv der Pharmazie

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On the basis of our previous results 22 salicylanilides were synthesized. The compounds were tested for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium kansasii, and Mycobacterium avium. The Free-Wilson method was used to evaluate structure-antimycobacterial activity relationships. 4-Chloro-N-(4-propylphenyl)salicylamide and 5-chloro-N-(4-propylphenyl)salicylamide were selected for preclinical studies.

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Section: Introductionmentioning

confidence: 99%

The Oriented Development of Antituberculotics: Salicylanilides

Waisser

Matyk

Divišová

et al. 2006

Archiv der Pharmazie

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“…The spin-trapping behavior of carbamoyl substituted derivatives toward different oxygen-and carbon-centered radicals has been reported. [18] Kinetics and mechanism for the reactions of N-methyl-N-phenylcarbamoyl chlorides with benzylamines in acetonitrile were reported by Koh et al [19] Matyk et al [20] reported the synthesis of a series of 64 derivatives of substituted heterocyclic analogues of salicylanilides, and the compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis, M. avium and two strains of M. kansasii. Methylene group modifications of the N-(isothiazol-5-yl)phenylacetamides synthesis and insecticidal activity were reported by Samaritoni et al [21] Several works have reported on the antimycobacterial benzylsalicylamides, [22,23] and the activity of isoesters of salicylanilides: 2-sulfanylbenzanilides, N-benzylsulfanylbenzamides 3-hydroxy picolinanilides, N-benzyl-3-hydroxypicolinamides.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic investigations and computational study of 2‐[acetyl(4‐bromophenyl)carbamoyl]‐4‐chlorophenyl acetate

Panicker¹,

Varghese

Mariamma³

et al. 2009

J Raman Spectroscopy

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The Fourier transform Raman (FT-Raman) and Fourier transform infrared (FT-IR) spectra of 2-[acetyl(4-bromophenyl)carbamoyl]-4-chlorophenyl acetate were studied. The vibrational wavenumbers were examined theoretically using the Gaussian03 set of quantum chemistry codes, and the normal modes were assigned by potential energy distribution (PED) calculations. The simultaneous Raman and infrared (IR) activations of the C O stretching mode in the carbamoyl moiety show a charge transfer interaction through a π-conjugated path. From the optimized structure, it is clear that the hydrogen bonding decreases the double bond character of the C O bond and increases the double bond character of the C-N bonds. The first hyperpolarizability and predicted IR intensities are reported. The calculated first hyperpolarizability is comparable with the reported values of similar structures, which makes this compound an attractive object for future studies of nonlinear optics. Optimized geometrical parameters of the compound are in agreement with similar reported structures.

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“…The development of new antituberculotic agents is the principal goal of our group. Lately, we have studied a number of structurally different compounds, such as the derivatives of salicylamides [1], pyridine [2,3], alkoxyphenylcarbamic acids [4], tetrazoles [5,6], dihydroindolethiones [7], and other heterocycles [8,9]. Our research was strongly oriented to collaborate with German institutes like Technical University Dresden, Friedrich Schiller University Jena, Hans Knöll Institute Jena, and Maxmilian University in Munich.…”

Section: Introductionmentioning

confidence: 97%

The Oriented Development of Antituberculotics (Part II): Halogenated 3‐(4‐Alkylphenyl)‐1,3‐benzoxazine‐2,4‐(3H)‐diones

Waisser¹,

Matyk

Divišová

et al. 2007

Archiv der Pharmazie

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Based on our previous studies, 21 new halogenated 3-(4-alkylphenyl)-1,3-benzoxazine-2,4-(3H)-diones were synthesized by the reaction of salicylanilides and methyl-chloroformate. All compounds were screened in vitro against three different strains of mycobacterium, and Free-Wilson method was used to establish structure-activity relationships. 6-Bromo-3-(4-butylphenyl)-1,3-benzoxazine-2,4-(3H)-dione 3b proved to be the most active compound of the series.

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Heterocyclic isosters of antimycobacterial salicylanilides

Cited by 22 publications

References 8 publications

The Oriented Development of Antituberculotics: Salicylanilides

The Oriented Development of Antituberculotics: Salicylanilides

Spectroscopic investigations and computational study of 2‐[acetyl(4‐bromophenyl)carbamoyl]‐4‐chlorophenyl acetate

The Oriented Development of Antituberculotics (Part II): Halogenated 3‐(4‐Alkylphenyl)‐1,3‐benzoxazine‐2,4‐(3H)‐diones

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