Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide
Identifikátory výsledku
Kód výsledku v IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F17%3A10365385" target="_blank" >RIV/00216208:11160/17:10365385 - isvavai.cz</a>
Nalezeny alternativní kódy
RIV/71009396:_____/17:N0000011
Výsledek na webu
<a href="http://www.sciencedirect.com/science/article/pii/S0960894X17310442" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0960894X17310442</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.bmcl.2017.10.050" target="_blank" >10.1016/j.bmcl.2017.10.050</a>
Alternativní jazyky
Jazyk výsledku
angličtina
Název v původním jazyce
Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide
Popis výsledku v původním jazyce
Reflecting the known biological activity of isoniazid-based hydrazones, seventeen hydrazones of 4-(trifluoromethyl) benzohydrazide as their bioisosters were synthesized from various benzaldehydes and aliphatic ketones. The compounds were screened for their in vitro activity against Mycobacterium tuberculosis, nontuberculous mycobacteria (M. avium, M. kansasii), bacterial and fungal strains. The most antimicrobial potent derivatives were also investigated for their cytostatic and cytotoxic properties against three cell lines. Camphor-based molecule, 4-(trifluoromethyl)-N'-(1,7,7-trimethylbicyclo[2.2.1] heptan-2-ylidene) benzohydrazide, exhibited the highest and selective inhibition of M. tuberculosis with the minimum inhibitory concentration (MIC) of 4 mu M, while N'-(4-chlorobenzylidene)-4-(trifluoromethyl) benzohydrazide was found to be superior against M. kansasii (MIC = 16 mu M). N'-(5-Chloro-2-hydroxybenzylidene)-4-(trifluoromethyl) benzohydrazide showed the lowest MIC values for gram-positive bacteria including methicillin-resistant Staphylococcus aureus as well as against two fungal strains of Candida glabrata and Trichophyton mentagrophytes within the range of <= 0.49-3.9 mu M. The convenient substitution of benzylidene moiety at the position 4 or the presence of 5-chloro-2-hydroxybenzylidene scaffold concomitantly with a sufficient lipophilicity are essential for the noticeable antimicrobial activity. This 5-chlorosalicylidene derivative avoided any cytotoxicity on two mammalian cell cultures (HepG2, BMM Phi) up to the concentration of 100 mu M, but it affected the growth of MonoMac6 cells.
Název v anglickém jazyce
Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide
Popis výsledku anglicky
Reflecting the known biological activity of isoniazid-based hydrazones, seventeen hydrazones of 4-(trifluoromethyl) benzohydrazide as their bioisosters were synthesized from various benzaldehydes and aliphatic ketones. The compounds were screened for their in vitro activity against Mycobacterium tuberculosis, nontuberculous mycobacteria (M. avium, M. kansasii), bacterial and fungal strains. The most antimicrobial potent derivatives were also investigated for their cytostatic and cytotoxic properties against three cell lines. Camphor-based molecule, 4-(trifluoromethyl)-N'-(1,7,7-trimethylbicyclo[2.2.1] heptan-2-ylidene) benzohydrazide, exhibited the highest and selective inhibition of M. tuberculosis with the minimum inhibitory concentration (MIC) of 4 mu M, while N'-(4-chlorobenzylidene)-4-(trifluoromethyl) benzohydrazide was found to be superior against M. kansasii (MIC = 16 mu M). N'-(5-Chloro-2-hydroxybenzylidene)-4-(trifluoromethyl) benzohydrazide showed the lowest MIC values for gram-positive bacteria including methicillin-resistant Staphylococcus aureus as well as against two fungal strains of Candida glabrata and Trichophyton mentagrophytes within the range of <= 0.49-3.9 mu M. The convenient substitution of benzylidene moiety at the position 4 or the presence of 5-chloro-2-hydroxybenzylidene scaffold concomitantly with a sufficient lipophilicity are essential for the noticeable antimicrobial activity. This 5-chlorosalicylidene derivative avoided any cytotoxicity on two mammalian cell cultures (HepG2, BMM Phi) up to the concentration of 100 mu M, but it affected the growth of MonoMac6 cells.
Klasifikace
Druh
J<sub>imp</sub> - Článek v periodiku v databázi Web of Science
CEP obor
—
OECD FORD obor
30104 - Pharmacology and pharmacy
Návaznosti výsledku
Projekt
<a href="/cs/project/GJ17-27514Y" target="_blank" >GJ17-27514Y: Peptidové drug delivery systémy směrované do makrofágů pro antimykobakteriálně aktivní sloučeniny</a><br>
Návaznosti
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Ostatní
Rok uplatnění
2017
Kód důvěrnosti údajů
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Údaje specifické pro druh výsledku
Název periodika
Bioorganic and Medicinal Chemistry Letters
ISSN
0960-894X
e-ISSN
—
Svazek periodika
27
Číslo periodika v rámci svazku
23
Stát vydavatele periodika
GB - Spojené království Velké Británie a Severního Irska
Počet stran výsledku
5
Strana od-do
5185-5189
Kód UT WoS článku
000415643400019
EID výsledku v databázi Scopus
2-s2.0-85032725839