Ultrasound-assisted green bromination of N-cinnamoyl amino acid amides - Structural characterization and antimicrobial evaluation

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F17%3A10367816" target="_blank" >RIV/00216208:11310/17:10367816 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.molstruc.2017.01.056" target="_blank" >http://dx.doi.org/10.1016/j.molstruc.2017.01.056</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2017.01.056" target="_blank" >10.1016/j.molstruc.2017.01.056</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Ultrasound-assisted green bromination of N-cinnamoyl amino acid amides - Structural characterization and antimicrobial evaluation

Popis výsledku v původním jazyce

N-phenylpropenoyl amino acid amides have been brominated using two alternative sonochemically activated green chemistry procedures. The first synthetic procedure has involved an ultrasound assisted bromination in an aqueous medium using ionic liquid as a catalyst of the reaction, whereas in the second one an in situ formation of Br-2 via oxidation of HBr by H2O2 has been used. For comparison, the conventional bromination procedure was also used. The newly brominated compounds were characterized by appropriate analytical techniques. A detailed NMR spectroscopic analysis and quantum chemical calculations using Density Functional Theory (DFT) methods have been used to define the stereochemistry of the products. The results confirmed the physicochemical identity and similar yields of the products obtained by the three synthetic procedures employed, and reveal the co-existence of two diastereoisomeric forms of the newly synthesized products. The antibacterial and antifungal activities of the dibrominated amides were evaluated.

Název v anglickém jazyce

Ultrasound-assisted green bromination of N-cinnamoyl amino acid amides - Structural characterization and antimicrobial evaluation

Popis výsledku anglicky

N-phenylpropenoyl amino acid amides have been brominated using two alternative sonochemically activated green chemistry procedures. The first synthetic procedure has involved an ultrasound assisted bromination in an aqueous medium using ionic liquid as a catalyst of the reaction, whereas in the second one an in situ formation of Br-2 via oxidation of HBr by H2O2 has been used. For comparison, the conventional bromination procedure was also used. The newly brominated compounds were characterized by appropriate analytical techniques. A detailed NMR spectroscopic analysis and quantum chemical calculations using Density Functional Theory (DFT) methods have been used to define the stereochemistry of the products. The results confirmed the physicochemical identity and similar yields of the products obtained by the three synthetic procedures employed, and reveal the co-existence of two diastereoisomeric forms of the newly synthesized products. The antibacterial and antifungal activities of the dibrominated amides were evaluated.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10608 - Biochemistry and molecular biology

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

—

Svazek periodika

1135

Číslo periodika v rámci svazku

May

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

9

Strana od-do

144-152

Kód UT WoS článku

000395604700017

EID výsledku v databázi Scopus

2-s2.0-85010638178