Methylace of akridin-9-ylthiomočovin. Struktura, fluorescence and biologické vlastnosti produktů

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F04%3A00011335" target="_blank" >RIV/60461373:22310/04:00011335 - isvavai.cz</a>

Výsledek na webu

—

DOI - Digital Object Identifier

—

Jazyk výsledku

angličtina

Název v původním jazyce

Methylation of Akridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products

Popis výsledku v původním jazyce

The structure, fluorescence, biological properties and S(N)-methylation reactions of ten 1,1-alkyl/aryl-disubstituted 3-(acridin-9-yl)thioureas 4 have been studied. Various reaction conditions allowed to obtain corresponding S-methyl 5 and S,N-dimethyl derivatives 6 in good yields. Structure and stereochemistry of the synthesized products are demonstrated by ab initio quantum chemical calculations and NMR techniques including PDQF-COSY, selective INEPT and NOE-difference experiments. Remarkable upfield13C shifts of resonance signals of carbons C-4a, C-10a adjacent to acridine N-10 are characteristic of hydroiodides in contrast to free bases. Z configuration in isothioureas 7 with secondary amino rest in relation to E configuration of isothioureas withprimary amino rest is discussed. Of the obtained products, some isothiourea salts 6 exhibit more than 2 orders of magnitude higher intensity of fluorescence, using 9-isothiocyanatoacridine as a standard. The obtained isothiourea hydroiod

Název v anglickém jazyce

Methylation of Akridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products

Popis výsledku anglicky

The structure, fluorescence, biological properties and S(N)-methylation reactions of ten 1,1-alkyl/aryl-disubstituted 3-(acridin-9-yl)thioureas 4 have been studied. Various reaction conditions allowed to obtain corresponding S-methyl 5 and S,N-dimethyl derivatives 6 in good yields. Structure and stereochemistry of the synthesized products are demonstrated by ab initio quantum chemical calculations and NMR techniques including PDQF-COSY, selective INEPT and NOE-difference experiments. Remarkable upfield13C shifts of resonance signals of carbons C-4a, C-10a adjacent to acridine N-10 are characteristic of hydroiodides in contrast to free bases. Z configuration in isothioureas 7 with secondary amino rest in relation to E configuration of isothioureas withprimary amino rest is discussed. Of the obtained products, some isothiourea salts 6 exhibit more than 2 orders of magnitude higher intensity of fluorescence, using 9-isothiocyanatoacridine as a standard. The obtained isothiourea hydroiod

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

—

Návaznosti

Z - Vyzkumny zamer (s odkazem do CEZ)

Rok uplatnění

2004

Kód důvěrnosti údajů

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

Název periodika

Collection of Czechoslovak Chemical Communications

ISSN

0010-0765

e-ISSN

—

Svazek periodika

69

Číslo periodika v rámci svazku

4

Stát vydavatele periodika

CZ - Česká republika

Počet stran výsledku

7

Strana od-do

833-849

Kód UT WoS článku

—

EID výsledku v databázi Scopus

—