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Salicylanilide esters of N-protected amino acids as novel antimicrobial agents
A Imramovsky, J Vinsova, JM Ferriz, V Buchta, J Jampilek
Language English Country Great Britain
NLK
ScienceDirect (archiv)
from 1993-01-01 to 2009-12-31
- MeSH
- Absidia drug effects MeSH
- Amino Acids chemistry MeSH
- Anti-Infective Agents pharmacology chemistry MeSH
- Aspergillus fumigatus drug effects MeSH
- Esters MeSH
- Financing, Organized MeSH
- Microbial Sensitivity Tests MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Salicylanilides pharmacology chemistry MeSH
- Trichophyton drug effects MeSH
A series of novel, highly antimicrobial salicylanilide esters of N-protected amino acids were synthesized and characterized. Their in vitro antimicrobial activity against eight fungal strains and Mycobacterium tuberculosis was determined. The compounds had the highest level of activity against Aspergillus fumigatus, Absidia corymbifera and Trichophyton mentagrophytes, and these levels were higher than that of the standard drug fluconazole. In addition, three compounds showed interesting antituberculosis activity, with inhibition ranging from 89% to 99%. (S)-4-Chloro-2-(4-trifluoromethylphenylcarbamoyl)-phenyl 2-benzyloxy-carbonylamino-propionate had the highest level of both antifungal and antimycobacterial activity. The structure-activity relationships of the new compounds are discussed.
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- $a eng
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- $a Imramovský, Aleš $7 xx0118877
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- $a Salicylanilide esters of N-protected amino acids as novel antimicrobial agents / $c A Imramovsky, J Vinsova, JM Ferriz, V Buchta, J Jampilek
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- $a Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic. ales.imramovsky@faf.cuni.cz
- 520 9_
- $a A series of novel, highly antimicrobial salicylanilide esters of N-protected amino acids were synthesized and characterized. Their in vitro antimicrobial activity against eight fungal strains and Mycobacterium tuberculosis was determined. The compounds had the highest level of activity against Aspergillus fumigatus, Absidia corymbifera and Trichophyton mentagrophytes, and these levels were higher than that of the standard drug fluconazole. In addition, three compounds showed interesting antituberculosis activity, with inhibition ranging from 89% to 99%. (S)-4-Chloro-2-(4-trifluoromethylphenylcarbamoyl)-phenyl 2-benzyloxy-carbonylamino-propionate had the highest level of both antifungal and antimycobacterial activity. The structure-activity relationships of the new compounds are discussed.
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- $a Absidia $x účinky léků $7 D020095
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- $a aminokyseliny $x chemie $7 D000596
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- $a antiinfekční látky $x farmakologie $x chemie $7 D000890
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- $a Aspergillus fumigatus $x účinky léků $7 D001232
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- $a salicylanilidy $x farmakologie $x chemie $7 D012458
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- $a Trichophyton $x účinky léků $7 D014249
- 650 _2
- $a financování organizované $7 D005381
- 700 1_
- $a Vinšová, Jarmila, $d 1951- $7 nlk19990073991
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- $a Ferriz, Juana Monreal
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- $a Buchta, Vladimír, $d 1960- $7 mzk2002156768
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- $a Jampílek, Josef $7 xx0027075
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- $t Bioorganic & Medicinal Chemistry Letters $w MED00000770 $g Roč. 19, č. 2 (2009), s. 348-351
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- $a 3
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- $a 2009 $b 19 $c 2 $d 348-351 $m Bioorganic & medicinal chemistry letters $n Bioorg Med Chem Lett $x MED00000770
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- $a 2011-1B09/dkme
