Synthesis of Readily Available Fluorophenylalanine Derivatives and Investigation of Their Biological Activity

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F17%3A39910632" target="_blank" >RIV/00216275:25310/17:39910632 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11160/17:10365384 RIV/71009396:_____/17:N0000005

Result on the web

<a href="https://doi.org/10.1016/j.bioorg.2017.02.010" target="_blank" >https://doi.org/10.1016/j.bioorg.2017.02.010</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.bioorg.2017.02.010" target="_blank" >10.1016/j.bioorg.2017.02.010</a>

Result language

angličtina

Original language name

Synthesis of Readily Available Fluorophenylalanine Derivatives and Investigation of Their Biological Activity

Original language description

A series of thirty novel N-acetylated fluorophenylalanine-based aromatic amides and esters was synthesized using N-(3-dimethylaminopropyl)-N0-ethylcarbodiimide or phosphorus trichloride in pyridine. They were characterized by spectral methods and screened against various microbes (Mycobacterium tuberculosis, non-tuberculous mycobacteria, other bacteria, fungi), for their inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) and cytotoxicity. All amino acids derivatives revealed a moderate inhibition of both cholinesterases with IC50 values for AChE and BChE of 57.88–130.75 mM and 8.25–289.0 mM, respectively. Some derivatives were comparable or superior to rivastigmine, an established drug. Phenyl 2-acetamido-3-(4-fluorophenyl)propanoate was identified as the selective and most potent inhibitor of BChE. The esterification and amidation of parent acids led to an improved BChE inhibition. The esters are better inhibitors of BChE than the amides. The introduction of NO2 and CH3 groups into aniline ring and CF3 moiety in phenol is translated into lower IC50 values. Seven compounds showed selectivity index higher than 10 for at least one cholinesterase. Especially the esters exhibited a mild activity against Gram-positive bacteria, mycobacteria and several fungal strains with minimum inhibitory concentrations starting from 125 mM. The highest susceptibility was recorded for Trichophyton mentagrophytes fungus.

Czech name

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Czech description

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Type

J_imp - 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

Project

<a href="/en/project/GJ17-27514Y" target="_blank" >GJ17-27514Y: Peptide Drug Delivery Systems Targeting Macrophages for Antimycobacterial Active Compounds</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2017

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Bioorganic Chemistry

ISSN

0045-2068

e-ISSN

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Volume of the periodical

71

Issue of the periodical within the volume

April

Country of publishing house

US - UNITED STATES

Number of pages

13

Pages from-to

244-256

UT code for WoS article

000404534300025

EID of the result in the Scopus database

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