Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents.

Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Research Abstract Details 

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Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Abstract Text:

Simone C B Gnoatto,Sophie Susplugas,Luciana Dalla Vechia,Thais B Ferreira,Alexandra Dassonville-Klimpt,Karine R Zimmer,Catherine Demailly,Sophie Da Nascimento,Jean Guillon,Philippe Grellier,Hugo Verli,Grace Gosmann,Pascal Sonnet,Simone C B Gnoatto,Sophie Susplugas,Luciana Dalla Vechia,Thais B Ferreira,Alexandra Dassonville-Klimpt,Karine R Zimmer,Catherine Demailly,Sophie Da Nascimento,Jean Guillon,Philippe Grellier,Hugo Verli,Grace Gosmann,Pascal Sonnet,

A series of new piperazine derivatives of ursolic acid was synthesized and tested against Plasmodium falciparum strains. They were also tested on their cytotoxicity effects upon MRC-5 cells. Seven new piperazinyl analogues showed significant activity in the nanomolar range (IC(50)=78-167nM) against Plasmodium falciparum CQ-resistant strain FcB1. A possible mechanism of interaction implicating binding of these compounds to beta-hematin was supported by in vitro tests. Moreover, the importance of the hydrophilic framework attached at the terminal nitrogen atom of the bis-(3-aminopropyl)piperazine joined to the triterpene ring was also explored through molecular dynamic simulations.

Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Publishing Authors By Initials

SC Gnoatto,S Susplugas,L Dalla Vechia,TB Ferreira,A Dassonville-Klimpt,KR Zimmer,C Demailly,S Da Nascimento,J Guillon,P Grellier,H Verli,G Gosmann,P Sonnet,SC Gnoatto,S Susplugas,L Dalla Vechia,TB Ferreira,A Dassonville-Klimpt,KR Zimmer,C Demailly,S Da Nascimento,J Guillon,P Grellier,H Verli,G Gosmann,P Sonnet,

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Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Bioorganic & medicinal chemistry

VOLUME: 16

Page Numbers: 771-82

Journal Abbreviation: Bioorg. Med. Chem.

ISSN: 1464-3391

DAY: 14

MONTH: 10

YEAR: 2007

Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Information

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LANGUAGE: eng

NlmUniqueID: 9413298

Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents. Keywords Mesh Terms:

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Grant and Affiliation Information for Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents.

AFFILIATION: Faculdade de Farmácia, Universidade Federal do Rio Grande do Sul (UFRGS), Av. Ipiranga, 2752, Porto Alegre 90610-000, RS, Brazil.

Country: England

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MEDLINETA: Bioorg Med Chem

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