Spectroscopic, structural and theoretical studies of novel, potentially cytotoxic 4-acridonecarboxamide imines

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F09%3A00021770" target="_blank" >RIV/60461373:22310/09:00021770 - isvavai.cz</a>

Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Spectroscopic, structural and theoretical studies of novel, potentially cytotoxic 4-acridonecarboxamide imines

Popis výsledku v původním jazyce

Ten novel, potentially intercalating 4-acridonecarboxamide azomethines and ketimines have been prepared by the condensation reaction of 9-oxo-9,10-dihydroacridine-4-carboxylic acid hydrazide with Various aldehydes and ketones. The structures of the compounds were characterized spectroscopically by NMR (H-1, C-13, N-15 nuclei and 2D experiments), UV-vis, IR and fluorescence methods and by quantum chemical calculations using DFT at the B3LYP/6-311+G(d,p) level of theory and semiempirical ZINDO and AMI methods. NMR chemical shift variations for C-4' were assessed due to changes in the polarizability of the imine C-4'=N-3' bond rather than direct inductive effects arising from the C-4' substituents. In concert with this was the reversed order observed forthe N-3' chemical shifts with DFT-calculated atomic charges confirming the bond polarization. Both intra- and intermolecular hydrogen bonds between the acridone NH hydrogen and the amidic carbonyl oxygen were found to exist by FT

Název v anglickém jazyce

Spectroscopic, structural and theoretical studies of novel, potentially cytotoxic 4-acridonecarboxamide imines

Popis výsledku anglicky

Ten novel, potentially intercalating 4-acridonecarboxamide azomethines and ketimines have been prepared by the condensation reaction of 9-oxo-9,10-dihydroacridine-4-carboxylic acid hydrazide with Various aldehydes and ketones. The structures of the compounds were characterized spectroscopically by NMR (H-1, C-13, N-15 nuclei and 2D experiments), UV-vis, IR and fluorescence methods and by quantum chemical calculations using DFT at the B3LYP/6-311+G(d,p) level of theory and semiempirical ZINDO and AMI methods. NMR chemical shift variations for C-4' were assessed due to changes in the polarizability of the imine C-4'=N-3' bond rather than direct inductive effects arising from the C-4' substituents. In concert with this was the reversed order observed forthe N-3' chemical shifts with DFT-calculated atomic charges confirming the bond polarization. Both intra- and intermolecular hydrogen bonds between the acridone NH hydrogen and the amidic carbonyl oxygen were found to exist by FT

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2009

Kód důvěrnosti údajů

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

Název periodika

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy

ISSN

1386-1425

e-ISSN

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Svazek periodika

73

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

11

Strana od-do

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Kód UT WoS článku

000266429700004

EID výsledku v databázi Scopus

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