Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain

Daniel P. Iwaniuk; Eric D. Whetmore; Nicholas Rosa; Kekeli Ekoue-Kovi; John Alumasa; Angel C. de Dios; Paul D. Roepe; Christian Wolf

doi:10.1016/j.bmc.2009.08.003

Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain

Daniel P. Iwaniuk
, Eric D. Whetmore
, Nicholas Rosa
, Kekeli Ekoue-Kovi
, John Alumasa
, Angel C. de Dios
, Paul D. Roepe
, Christian Wolf

Biochemistry & Molecular Biology

Research output: Contribution to journal › Article › peer-review

44 Scopus citations

Abstract

We report the synthesis and in vitro antimalarial activity of several new 4-amino- and 4-alkoxy-7-chloroquinolines carrying a linear dibasic side chain. Many of these chloroquine analogues have submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strain of Plasmodium falciparum) and low resistance indices were obtained in most cases. Importantly, compounds 11-15 and 24 proved to be more potent against Dd2 than chloroquine. Branching of the side chain structure proved detrimental to the activity against the CQR strain.

Original language	English (US)
Pages (from-to)	6560-6566
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	18
DOIs	https://doi.org/10.1016/j.bmc.2009.08.003
State	Published - Sep 15 2009

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmc.2009.08.003

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title = "Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain",

abstract = "We report the synthesis and in vitro antimalarial activity of several new 4-amino- and 4-alkoxy-7-chloroquinolines carrying a linear dibasic side chain. Many of these chloroquine analogues have submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strain of Plasmodium falciparum) and low resistance indices were obtained in most cases. Importantly, compounds 11-15 and 24 proved to be more potent against Dd2 than chloroquine. Branching of the side chain structure proved detrimental to the activity against the CQR strain.",

author = "Iwaniuk, \{Daniel P.\} and Whetmore, \{Eric D.\} and Nicholas Rosa and Kekeli Ekoue-Kovi and John Alumasa and \{de Dios\}, \{Angel C.\} and Roepe, \{Paul D.\} and Christian Wolf",

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AU - Iwaniuk, Daniel P.

AU - Whetmore, Eric D.

AU - Rosa, Nicholas

AU - Ekoue-Kovi, Kekeli

AU - Alumasa, John

AU - de Dios, Angel C.

AU - Roepe, Paul D.

AU - Wolf, Christian

PY - 2009/9/15

Y1 - 2009/9/15

N2 - We report the synthesis and in vitro antimalarial activity of several new 4-amino- and 4-alkoxy-7-chloroquinolines carrying a linear dibasic side chain. Many of these chloroquine analogues have submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strain of Plasmodium falciparum) and low resistance indices were obtained in most cases. Importantly, compounds 11-15 and 24 proved to be more potent against Dd2 than chloroquine. Branching of the side chain structure proved detrimental to the activity against the CQR strain.

AB - We report the synthesis and in vitro antimalarial activity of several new 4-amino- and 4-alkoxy-7-chloroquinolines carrying a linear dibasic side chain. Many of these chloroquine analogues have submicromolar antimalarial activity versus HB3 (chloroquine sensitive) and Dd2 (chloroquine resistant strain of Plasmodium falciparum) and low resistance indices were obtained in most cases. Importantly, compounds 11-15 and 24 proved to be more potent against Dd2 than chloroquine. Branching of the side chain structure proved detrimental to the activity against the CQR strain.

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ER -

Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain

Abstract

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