Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide
The result's identifiers
Result code in 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>
Alternative codes found
RIV/71009396:_____/17:N0000011
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Synthesis and biological evolution of hydrazones derived from 4-(trifluoromethyl)benzohydrazide
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
30104 - Pharmacology and pharmacy
Result continuities
Project
<a href="/en/project/GJ17-27514Y" target="_blank" >GJ17-27514Y: Peptide Drug Delivery Systems Targeting Macrophages for Antimycobacterial Active Compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Bioorganic and Medicinal Chemistry Letters
ISSN
0960-894X
e-ISSN
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Volume of the periodical
27
Issue of the periodical within the volume
23
Country of publishing house
GB - UNITED KINGDOM
Number of pages
5
Pages from-to
5185-5189
UT code for WoS article
000415643400019
EID of the result in the Scopus database
2-s2.0-85032725839