Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines

S. Vandekerckhove; C. Mueller; D. Vogt; C. Lategan; P.J. Smith; K. Chibale; N. Kimpe, de; M.W.A. D'hooghe

doi:10.1016/j.bmcl.2012.10.094

Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines

S. Vandekerckhove, C. Mueller, D. Vogt, C. Lategan, P.J. Smith, K. Chibale, N. Kimpe, de, M.W.A. D'hooghe

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Abstract

A variety of 5-, 6- and 8-(4-aminobutyloxy)quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of these new quinolines revealed micromolar potency for all representatives against a chloroquine-sensitive strain of Plasmodium falciparum, and three compounds showed submicromolar activity against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 150 and 680 nM.

Original language	English
Pages (from-to)	318-322
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	1
DOIs	https://doi.org/10.1016/j.bmcl.2012.10.094
Publication status	Published - 2013

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title = "Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines",

abstract = "A variety of 5-, 6- and 8-(4-aminobutyloxy)quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of these new quinolines revealed micromolar potency for all representatives against a chloroquine-sensitive strain of Plasmodium falciparum, and three compounds showed submicromolar activity against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 150 and 680 nM.",

author = "S. Vandekerckhove and C. Mueller and D. Vogt and C. Lategan and P.J. Smith and K. Chibale and {Kimpe, de}, N. and M.W.A. D'hooghe",

year = "2013",

doi = "10.1016/j.bmcl.2012.10.094",

language = "English",

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AU - Vandekerckhove, S.

AU - Mueller, C.

AU - Vogt, D.

AU - Lategan, C.

AU - Smith, P.J.

AU - Chibale, K.

AU - Kimpe, de, N.

AU - D'hooghe, M.W.A.

PY - 2013

Y1 - 2013

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AB - A variety of 5-, 6- and 8-(4-aminobutyloxy)quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of these new quinolines revealed micromolar potency for all representatives against a chloroquine-sensitive strain of Plasmodium falciparum, and three compounds showed submicromolar activity against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 150 and 680 nM.

U2 - 10.1016/j.bmcl.2012.10.094

DO - 10.1016/j.bmcl.2012.10.094

M3 - Article

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SN - 0960-894X

VL - 23

SP - 318

EP - 322

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 1

ER -

Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines

Abstract

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