Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives

Kód výsledku v IS VaVaI

RIV/61989592:15310/12:33141460 - isvavai.cz

Výsledek na webu

http://dx.doi.org/10.1021/co300124q

DOI - Digital Object Identifier

10.1021/co300124q

Jazyk výsledku

angličtina

Název v původním jazyce

Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives

Popis výsledku v původním jazyce

Solid-phase synthesis of 3,4-dihydro-benzo[e][1,4]diazepin-5-ones with three diversity positions is described. Various primary amines were used as the starting material and immobilized on the polystyrene resin equipped with different acid-labile linkers.Polymer supported amines were converted to ?-aminoketones with the use of their sulfonylation with the 4-nitrobenzensulfonylchoride (4-Nos-Cl) and subsequent alkylation with alfa-bromoketones. After the cleavage of the 4-Nos group the corresponding -aminoketones were acylated with various o-nitrobenzoic acids. Reduction of the nitro group followed by spontaneous on-resin ring closure gave the target immobilized benzodiazepines. After acid-mediated cleavage the products were obtained in very good, crudepurity and satisfactory yields which makes the developed method applicable for simple library synthesis of the corresponding derivatives in a combinatorial fashion.

Název v anglickém jazyce

Solid-Phase Synthesis of Trisubstituted Benzo[1,4]-Diazepin-5-one Derivatives

Popis výsledku anglicky

Solid-phase synthesis of 3,4-dihydro-benzo[e][1,4]diazepin-5-ones with three diversity positions is described. Various primary amines were used as the starting material and immobilized on the polystyrene resin equipped with different acid-labile linkers.Polymer supported amines were converted to ?-aminoketones with the use of their sulfonylation with the 4-nitrobenzensulfonylchoride (4-Nos-Cl) and subsequent alkylation with alfa-bromoketones. After the cleavage of the 4-Nos group the corresponding -aminoketones were acylated with various o-nitrobenzoic acids. Reduction of the nitro group followed by spontaneous on-resin ring closure gave the target immobilized benzodiazepines. After acid-mediated cleavage the products were obtained in very good, crudepurity and satisfactory yields which makes the developed method applicable for simple library synthesis of the corresponding derivatives in a combinatorial fashion.

Druh

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

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

ED0030/01/01: Biomedicína pro regionální rozvoj a lidské zdroje

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2012

Kód důvěrnosti údajů

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

Název periodika

ACS Combinatorial Science

ISSN

2156-8952

e-ISSN

—

Svazek periodika

14

Číslo periodika v rámci svazku

12

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

6

Strana od-do

651-656

Kód UT WoS článku

000312122500004

EID výsledku v databázi Scopus

—