Publication detail

Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres

Year: 2012

Type of publication: článek v odborném periodiku

Name of source: Molecules

Publisher name: Molecular Diversity Preservation International

Place: Basel

Page from-to: 613-644

Titles:

Language	Name	Abstract	Keywords
cze	Zkoumání spektra biologické aktivity substituovaných chinolin-2-carboxamidů a jejich isosterů	V této studii byla připravena a charakterizována série 35 substituovaných chinolin-2-karboxamidů a 33 substituovaných naftalen-2-karboxamidů. Tyto látky byly testovány na aktivitu spojenou s inhibicí elektronového transportu při fotosyntéze (PET) v chloroplastech špenátu (Spinacia oleracea L.). Primární in vitro screening připravených sloučenin byl rovněž proveden proti 4 mykobakteriálním druhům. N-Cykloheptylchinolin-2-karboxamid, N-cyklohexylchinolin-2-karboxamid a N-(2-fenylethyl)chinolin-2-karboxamid vykázaly vyšší aktivitu proti M. tuberculosis než standardy isoniazid nebo pyrazinamid a 2-(pyrrolidin-1-ylkarbonyl)chinolin a 1-(2-naftoyl)pyrrolidin ukázal vyšší aktivitu proti M. kansasii a M. avium paratuberculosis než standardy isoniazid nebo pyrazinamid. Njefektivnější antimykobakteriální sloučenina vykazuje nevýznamnou toxicitu vůči THP-1 buňkám lidské monocytické leukemie. PET-inhibice vyjádřená IC50 hodnotou byla u nejaktivnějšího N-benzyl-2-naftamidu 7.5 mu mol/L. U všech sloučenin byly diskutovány vztahy struktura-aktivita.	biologická aktivita; chinolin-2-carboxamidy; salicylanilidy
eng	Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres	In this study, a series of thirty-five substituted quinoline-2-carboxamides and thirty-three substituted naphthalene-2-carboxamides were prepared and characterized. They were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial species. N-Cycloheptylquinoline-2-carboxamide, N-cyclohexylquinoline-2-carboxamide and N-(2-phenylethyl)quinoline-2-carboxamide showed higher activity against M. tuberculosis than the standards isoniazid or pyrazinamide and 2-(pyrrolidin-1-ylcarbonyl)quinoline and 1-(2-naphthoyl)pyrrolidine expressed higher activity against M. kansasii and M. avium paratuberculosis than the standards isoniazid or pyrazinamide. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound N-benzyl-2-naphthamide was 7.5 mu mol/L. For all compounds, the structure-activity relationships are discussed.	QUINOLINE ANALOGS; PYRAZINECARBOXAMIDES; SALICYLANILIDES; ANTIFUNGAL; HERBICIDE; quinolines; naphthalene; lipophilicity; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro antimycobacterial activity; in vitro cytotoxicity

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