• Je něco špatně v tomto záznamu ?

Synthesis, antimycobacterial, antifungal and photosynthesis-inhibiting activity of chlorinated N-phenylpyrazine-2-carboxamides

M. Dolezal, J. Zitko, Z. Osicka, J. Kunes, M. Vejsova, V. Buchta, J. Dohnal, J. Jampilek, K. Kralova

. 2010 ; 15 (12) : 8567-8581. [pub] 20101126

Jazyk angličtina Země Švýcarsko

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/bmc12026610

Grantová podpora
NS10367 MZ0 CEP - Centrální evidence projektů

A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal activity, and for their ability to inhibit photosynthetic electron transport (PET). 6-Chloro-N-(4-chlorophenyl)pyrazine-2-carboxamide manifested the highest activity against Mycobacterium tuberculosis strain H37Rv (65% inhibition at 6.25 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 6-chloro-5-tert-butyl-N-(3,4-dichlorophenyl)pyrazine-2-carboxamide (MIC=62.5 μmol/L). 6-chloro-5-tert-butyl-N-(4-chlorophenyl)pyrazine-2-carboxamide showed the highest PET inhibition in spinach chloroplasts (Spinacia oleracea L.) chloroplasts (IC50=43.0 μmol/L). 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.

Citace poskytuje Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc12026610
003      
CZ-PrNML
005      
20160301060012.0
007      
ta
008      
120816s2010 sz f 000 0#eng||
009      
AR
024    7_
$a 10.3390/molecules15128567 $2 doi
035    __
$a (PubMed)21116226
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a sz
100    1_
$a Doležal, Martin, $7 jn19981000714 $u Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Hradec Kralove, Czech Republic. martin.dolezal@faf.cuni.cz $d 1961-
245    10
$a Synthesis, antimycobacterial, antifungal and photosynthesis-inhibiting activity of chlorinated N-phenylpyrazine-2-carboxamides / $c M. Dolezal, J. Zitko, Z. Osicka, J. Kunes, M. Vejsova, V. Buchta, J. Dohnal, J. Jampilek, K. Kralova
520    9_
$a A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal activity, and for their ability to inhibit photosynthetic electron transport (PET). 6-Chloro-N-(4-chlorophenyl)pyrazine-2-carboxamide manifested the highest activity against Mycobacterium tuberculosis strain H37Rv (65% inhibition at 6.25 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 6-chloro-5-tert-butyl-N-(3,4-dichlorophenyl)pyrazine-2-carboxamide (MIC=62.5 μmol/L). 6-chloro-5-tert-butyl-N-(4-chlorophenyl)pyrazine-2-carboxamide showed the highest PET inhibition in spinach chloroplasts (Spinacia oleracea L.) chloroplasts (IC50=43.0 μmol/L). 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.
650    _2
$a antibakteriální látky $x chemická syntéza $x chemie $x farmakologie $7 D000900
650    _2
$a antifungální látky $x chemická syntéza $x chemie $x farmakologie $7 D000935
650    _2
$a chloroplasty $x metabolismus $7 D002736
650    _2
$a chlorované uhlovodíky $x chemická syntéza $x chemie $x farmakologie $7 D006843
650    _2
$a molekulární struktura $7 D015394
650    _2
$a Mycobacterium tuberculosis $x růst a vývoj $7 D009169
650    _2
$a fotosyntéza $x účinky léků $7 D010788
650    _2
$a pyrazinamid $x analogy a deriváty $x chemická syntéza $x chemie $x farmakologie $7 D011718
650    _2
$a Spinacia oleracea $x metabolismus $7 D018724
650    _2
$a vztahy mezi strukturou a aktivitou $7 D013329
650    _2
$a Trichophyton $x růst a vývoj $7 D014249
655    _2
$a časopisecké články $7 D016428
655    _2
$a práce podpořená grantem $7 D013485
700    1_
$a Zitko, Jan $7 xx0230408 $u Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Hradec Kralove, Czech Republic
700    1_
$a Osicka, Zdenek $u Bioveta a.s., Ivanovice na Hane, Czech Republic
700    1_
$a Kuneš, Jiří, $d 1965- $7 xx0105105 $u Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Hradec Kralove, Czech Republic
700    1_
$a Vejsová, Marcela $7 xx0106227 $u Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Hradec Kralove, Czech Republic
700    1_
$a Buchta, Vladimír, $d 1960- $7 mzk2002156768 $u Department of Clinical Microbiology, Faculty of Medicine and University Hospital, Charles University in Prague, Hradec Kralove, Czech Republic
700    1_
$a Dohnal, Jiří, $d 1955- $7 xx0063747 $u Zentiva k.s., Prague, Czech Republic; Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno, Czech Republic
700    1_
$a Jampílek, Josef $7 xx0027075 $u Zentiva k.s., Prague, Czech Republic; Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno, Czech Republic
700    1_
$a Kralova, Katarina $u Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Bratislava, Slovak Republic
773    0_
$w MED00180394 $t Molecules (Basel, Switzerland) $x 1420-3049 $g Roč. 15, č. 12 (2010), s. 8567-8581
856    41
$u https://pubmed.ncbi.nlm.nih.gov/21116226 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y m $z 0
990    __
$a 20120816 $b ABA008
991    __
$a 20160301060025 $b ABA008
999    __
$a ok $b bmc $g 948652 $s 783956
BAS    __
$a 3
BAS    __
$a PreBMC
BMC    __
$a 2010 $b 15 $c 12 $d 8567-8581 $e 20101126 $i 1420-3049 $m Molecules $n Molecules $x MED00180394
GRA    __
$a NS10367 $p MZ0
LZP    __
$b NLK122 $a Pubmed-20120816/11/01

Najít záznam

Citační ukazatele

Možnosti archivace