-
Je něco špatně v tomto záznamu ?
Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide
M. Krátký, S. Bősze, Z. Baranyai, J. Stolaříková, J. Vinšová,
Jazyk angličtina Země Velká Británie
Typ dokumentu časopisecké články, práce podpořená grantem
- MeSH
- antiinfekční látky chemická syntéza farmakologie toxicita MeSH
- buněčné linie MeSH
- buňky Hep G2 MeSH
- Candida glabrata účinky léků MeSH
- hydrazony chemie farmakologie toxicita MeSH
- lidé MeSH
- mikrobiální testy citlivosti MeSH
- Mycobacterium avium komplex účinky léků MeSH
- Mycobacterium kansasii účinky léků MeSH
- Mycobacterium tuberculosis účinky léků MeSH
- myši MeSH
- viabilita buněk účinky léků MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
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 µM, while N'-(4-chlorobenzylidene)-4-(trifluoromethyl)benzohydrazide was found to be superior against M. kansasii (MIC = 16 µM). 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 µM. 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, BMMΦ) up to the concentration of 100 µM, but it affected the growth of MonoMac6 cells.
Citace poskytuje Crossref.org
- 000
- 00000naa a2200000 a 4500
- 001
- bmc18016248
- 003
- CZ-PrNML
- 005
- 20180517091716.0
- 007
- ta
- 008
- 180515s2017 xxk f 000 0|eng||
- 009
- AR
- 024 7_
- $a 10.1016/j.bmcl.2017.10.050 $2 doi
- 035 __
- $a (PubMed)29097168
- 040 __
- $a ABA008 $b cze $d ABA008 $e AACR2
- 041 0_
- $a eng
- 044 __
- $a xxk
- 100 1_
- $a Krátký, Martin $u Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. Electronic address: martin.kratky@faf.cuni.cz.
- 245 10
- $a Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide / $c M. Krátký, S. Bősze, Z. Baranyai, J. Stolaříková, J. Vinšová,
- 520 9_
- $a 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 µM, while N'-(4-chlorobenzylidene)-4-(trifluoromethyl)benzohydrazide was found to be superior against M. kansasii (MIC = 16 µM). 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 µM. 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, BMMΦ) up to the concentration of 100 µM, but it affected the growth of MonoMac6 cells.
- 650 _2
- $a zvířata $7 D000818
- 650 _2
- $a antiinfekční látky $x chemická syntéza $x farmakologie $x toxicita $7 D000890
- 650 _2
- $a Candida glabrata $x účinky léků $7 D041221
- 650 _2
- $a buněčné linie $7 D002460
- 650 _2
- $a viabilita buněk $x účinky léků $7 D002470
- 650 _2
- $a buňky Hep G2 $7 D056945
- 650 _2
- $a lidé $7 D006801
- 650 _2
- $a hydrazony $x chemie $x farmakologie $x toxicita $7 D006835
- 650 _2
- $a myši $7 D051379
- 650 _2
- $a mikrobiální testy citlivosti $7 D008826
- 650 _2
- $a Mycobacterium avium komplex $x účinky léků $7 D015269
- 650 _2
- $a Mycobacterium kansasii $x účinky léků $7 D019909
- 650 _2
- $a Mycobacterium tuberculosis $x účinky léků $7 D009169
- 655 _2
- $a časopisecké články $7 D016428
- 655 _2
- $a práce podpořená grantem $7 D013485
- 700 1_
- $a Bősze, Szilvia $u MTA-ELTE Research Group of Peptide Chemistry, Eötvös Loránd University, Pázmány Péter Sétány 1/A, Budapest, H-1117, P.O. Box 32, 1518 Budapest 112, Hungary.
- 700 1_
- $a Baranyai, Zsuzsa $u MTA-ELTE Research Group of Peptide Chemistry, Eötvös Loránd University, Pázmány Péter Sétány 1/A, Budapest, H-1117, P.O. Box 32, 1518 Budapest 112, Hungary.
- 700 1_
- $a Stolaříková, Jiřina $u Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské náměstí 7, 702 00 Ostrava, Czech Republic.
- 700 1_
- $a Vinšová, Jarmila $u Department of Organic and Bioorganic Chemistry, Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic.
- 773 0_
- $w MED00000770 $t Bioorganic & medicinal chemistry letters $x 1464-3405 $g Roč. 27, č. 23 (2017), s. 5185-5189
- 856 41
- $u https://pubmed.ncbi.nlm.nih.gov/29097168 $y Pubmed
- 910 __
- $a ABA008 $b sig $c sign $y a $z 0
- 990 __
- $a 20180515 $b ABA008
- 991 __
- $a 20180517091852 $b ABA008
- 999 __
- $a ok $b bmc $g 1299872 $s 1013088
- BAS __
- $a 3
- BAS __
- $a PreBMC
- BMC __
- $a 2017 $b 27 $c 23 $d 5185-5189 $e 20171021 $i 1464-3405 $m Bioorganic & medicinal chemistry letters $n Bioorg Med Chem Lett $x MED00000770
- LZP __
- $a Pubmed-20180515
