Informace o publikaci
Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides
| Autoři | |
|---|---|
| Rok publikování | 2014 |
| Druh | Článek v odborném periodiku |
| Časopis / Zdroj | Molecules |
| Fakulta / Pracoviště MU | |
| Citace | |
| www | http://apps.webofknowledge.com/full_record.do?product=WOS&search_mode=GeneralSearch&qid=1&SID=F1crF62WD2aQBykkCNF&page=1&doc=10 |
| Doi | http://dx.doi.org/10.3390/molecules190710386 |
| Klíčová slova | naphthalene; lipophilicity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; spinach chloroplasts |
| Popis | In this study, a series of twenty-two ring-substituted naphthalene-1-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized carboxanilides was performed against Mycobacterium avium subsp. paratuberculosis. N-(2-Methoxyphenyl) naphthalene-1-carboxamide, N-(3-methoxyphenyl) naphthalene-1-carboxamide, N-(3-methylphenyl) naphthalene-1-carboxamide, N-(4-methylphenyl) naphthalene-1-carboxamide and N-(3-fluorophenyl) naphthalene-1-carboxamide showed against M. avium subsp. paratuberculosis two-fold higher activity than rifampicin and three-fold higher activity than ciprofloxacin. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The testing of biological activity of the compounds was completed with the study of photosynthetic electron transport (PET) inhibition in isolated spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity expressed by IC50 value of the most active compound N-[4-( trifluoromethyl) phenyl]naphthalene-1-carboxamide was 59 mu mol/L. The structure-activity relationships are discussed. |