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Synthesis and pharmacological investigation of new N-hydroxyalkyl-2-aminophenothiazines exhibiting marked MDR inhibitory effect

Takács, Daniella and Egyed, Orsolya and Drahos, László and Szabó, Pál and Jemnitz, Katalin and Szabó, Mónika and Veres, Zsuzsa and Visy, Julia and Molnár, József and Riedl, Zsuzsanna and Hajós, György (2013) Synthesis and pharmacological investigation of new N-hydroxyalkyl-2-aminophenothiazines exhibiting marked MDR inhibitory effect. BIOORGANIC & MEDICINAL CHEMISTRY, 21 (13). pp. 3760-3779. ISSN 0968-0896

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Abstract

Novel N-hydroxyalkyl-2-aminophenothiazines implying a tetrazole moiety at the alkyl chain have been synthesized by hydroboration-oxidation of dienes followed by Buchwald-Hartwig cross-coupling reaction. Also, some sulfoxide and sulfone derivatives have been prepared by selective oxidations. MDR inhibition studies on rat hepatocyte cell culture revealed that some derivatives exhibit marked biological efficacy exceeding that of the standard verapamil (e.g. 3h, 4h, 16). Selected derivatives were subjected to chemical resolution to provide both enantiomers which were shown of similar activity on P-gp interaction measurements. The new compounds exhibited no toxicity

Item Type: Article
Uncontrolled Keywords: N-hydroxyalkyl-2-aminophenothiazines Sulfoxide and sulfone derivatives MDR inhibition Buchwald-Hartwig cross-coupling reaction Resolution of racemate
Subjects: Q Science / természettudomány > QD Chemistry / kémia
Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
R Medicine / orvostudomány > RS Pharmacy and materia medica / gyógyszerészet, gyógyászati eszközök
Depositing User: Dr. xAranka xPilbáth
Date Deposited: 04 Oct 2013 09:40
Last Modified: 05 Apr 2023 07:05
URI: http://real.mtak.hu/id/eprint/6839

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