Preparation and Biological Properties of Ring-Substituted
Naphthalene-1-Carboxanilides

J 2014

Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides

GONEC, Tomas; Jiri KOS; Eoghan NEVIN; Rodney GOVENDER; Matus PESKO et. al.

Základní údaje

Originální název

Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides

Autoři

GONEC, Tomas; Jiri KOS; Eoghan NEVIN; Rodney GOVENDER; Matus PESKO; Jan TENGLER a Ivan KUSHKEVYCH

Vydání

Molecules, Basel, Mayer und Muller, 2014, 1420-3049

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10606 Microbiology

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 2.416

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.3390/molecules190710386

UT WoS

000340036200104

EID Scopus

2-s2.0-84904786341

Klíčová slova anglicky

naphthalene; lipophilicity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; spinach chloroplasts

Štítky

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 21. 10. 2019 09:27, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

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.

Citovat

GONEC, Tomas; Jiri KOS; Eoghan NEVIN; Rodney GOVENDER; Matus PESKO; Jan TENGLER a Ivan KUSHKEVYCH. Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides. Molecules. Basel: Mayer und Muller, 2014, roč. 19, č. 7, s. 10386-10409. ISSN 1420-3049. Dostupné z: https://doi.org/10.3390/molecules190710386.

@article{1413050,
   author = {Gonec, Tomas and Kos, Jiri and Nevin, Eoghan and Govender, Rodney and Pesko, Matus and Tengler, Jan and Kushkevych, Ivan},
   article_location = {Basel},
   article_number = {7},
   doi = {https://doi.org/10.3390/molecules190710386},
   keywords = {naphthalene; lipophilicity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; spinach chloroplasts},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   note = {žádný z autorů nemá na WoS afiliaci na MU, nelze tedy výsledek přenášet do RIV!},
   title = {Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides},
   url = {http://apps.webofknowledge.com/full_record.do?product=WOS&search_mode=GeneralSearch&qid=1&SID=F1crF62WD2aQBykkCNF&page=1&doc=10},
   volume = {19},
   year = {2014}
}

TY  - JOUR
ID  - 1413050
AU  - Gonec, Tomas - Kos, Jiri - Nevin, Eoghan - Govender, Rodney - Pesko, Matus - Tengler, Jan - Kushkevych, Ivan
PY  - 2014
TI  - Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides
JF  - Molecules
VL  - 19
IS  - 7
SP  - 10386-10409
EP  - 10386-10409
PB  - Mayer und Muller
SN  - 14203049
N1  - žádný z autorů nemá na WoS afiliaci na MU, nelze tedy výsledek přenášet do RIV!
KW  - naphthalene
KW  - lipophilicity
KW  - in vitro antimycobacterial activity
KW  - in vitro cytotoxicity
KW  - photosynthetic electron transport inhibition
KW  - spinach chloroplasts
UR  - http://apps.webofknowledge.com/full_record.do?product=WOS&search_mode=GeneralSearch&qid=1&SID=F1crF62WD2aQBykkCNF&page=1&doc=10
N2  - 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.
ER  -

GONEC, Tomas; Jiri KOS; Eoghan NEVIN; Rodney GOVENDER; Matus PESKO; Jan TENGLER a Ivan KUSHKEVYCH. Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides. \textit{Molecules}. Basel: Mayer und Muller, 2014, roč.~19, č.~7, s.~10386-10409. ISSN~1420-3049. Dostupné z: https://doi.org/10.3390/molecules190710386.

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