905927-80-2Relevant academic research and scientific papers
Investigating spectrum of biological activity of 4- and 5-Chloro-2-hydroxy-N-[2-(arylamino)-1-alkyl-2-oxoethyl]benzamides
Imramovsky, Ales,Pesko, Matus,Kralova, Katarina,Vejsova, Marcela,Stolarikova, Jirina,Vinsova, Jarmila,Jampilek, Josef
scheme or table, p. 2414 - 2430 (2011/05/05)
In this study, a series of twenty-two 5-chloro-2-hydroxy-N-[2-(arylamino)- 1- alkyl-2-oxoethyl]benzamides and ten 4-chloro-2-hydroxy-N-[2-(arylamino)-1- alkyl-2- oxoethyl]benzamides is described. The compounds were analyzed using RP-HPLC to determine lipophilicity. Primary in vitro screening of the synthesized compounds was performed against mycobacterial, bacterial and fungal strains. They were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The compounds showed biological activity comparable with or higher than the standards isoniazid, fluconazole, penicillin G or ciprofloxacin. For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed.
Salicylanilide esters of N-protected amino acids as novel antimicrobial agents
Imramovsky, Ales,Vinsova, Jarmila,Ferriz, Juana Monreal,Buchta, Vladimir,Jampilek, Josef
, p. 348 - 351 (2011/03/18)
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.
Salicylanilide esterification: unexpected formation of novel seven-membered rings
Imramovsky, Ale?,Vin?ová, Jarmila,Férriz, Juana Monreal,Kune?, Ji?í,Pour, Milan,Dole?al, Martin
, p. 5007 - 5011 (2007/10/03)
Novel benzoxazepines were prepared upon esterification of biologically active salicylanilides with some N-protected amino acids. While the desired conjugates of the salicylanilides with the amino acids were obtained when sterically more demanding amino acids were used, benzoxazepines were formed as a result of a seven-exo-trig cyclization in the case of N-protected glycine and alanine. The structures of the products were confirmed by 2D NMR methods, and further transformations of the acyclic conjugates provided additional support for the proposed mechanism of cyclization.
