New derivatives of 7-chloroquinolin-4-amine with antiprotozoal activity

被引：6

作者：

Faist, Johanna ^{[1
]}

Hinteregger, Clemens ^{[1
]}

Seebacher, Werner ^{[1
]}

Saf, Robert ^{[2
]}

Maser, Pascal ^{[3
,4
]}

Kaiser, Marcel ^{[3
,4
]}

Weis, Robert ^{[1
]}

机构：

[1] Graz Univ, Pharmaceut Chem, Inst Pharmaceut Sci, A-8010 Graz, Austria

[2] Graz Univ Technol, Inst Chem & Technol Mat, A-8010 Graz, Austria

[3] Swiss Trop & Publ Hlth Inst, Basel, Switzerland

[4] Univ Basel, CH-4003 Basel, Switzerland

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2017年 / 25卷 / 03期

关键词：

Amines; Antiplasmodial activity; Heterocycles; NMR spectroscopy; Nucleophilic substitutions; Quinoline; PLASMODIUM-FALCIPARUM; TRYPANOSOMA-BRUCEI; DRUG-RESISTANCE; ASSAY; SUSCEPTIBILITY; SENSITIVITY; RHODESIENSE; INVITRO;

D O I：

10.1016/j.bmc.2016.12.006

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Novel co-aminoacyl and -alkyl derivatives of 7-chloroquinolin-4-amine were prepared and their structures confirmed by NMR spectroscopy. Their antiprotozoal activities were examined in vitro against the sensitive NF54 strain as well as against the multiresistant K-1 strain of Plasmodium falciparum and against Trypanosoma brucei rhodesiense (STIB 900). The results were compared with the activities of clinically used drugs. Their antitypanosomal activities were only moderate whereas their antiplasmodial activities looked very promising. Some were equal or slightly more active than chloroquine against the sensitive strain. However, in comparison to chloroquine, the activity of the new compounds was decreased much less in the resistant strain. Several possessed activity against both strains in low nanomolar concentration. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：941 / 948

页数：8

共 24 条

[1] A NEW RAPID AND SIMPLE NONRADIOACTIVE ASSAY TO MONITOR AND DETERMINE THE PROLIFERATION OF LYMPHOCYTES - AN ALTERNATIVE TO [H-3] THYMIDINE INCORPORATION ASSAY [J].

AHMED, SA ;

GOGAL, RM ;

WALSH, JE .

JOURNAL OF IMMUNOLOGICAL METHODS, 1994, 170 (02) :211-224

[2] CULTIVATION IN A SEMI-DEFINED MEDIUM OF ANIMAL INFECTIVE FORMS OF TRYPANOSOMA-BRUCEI, TRYPANOSOMA-EQUIPERDUM, TRYPANOSOMA-EVANSI, TRYPANOSOMA-RHODESIENSE AND T-GAMBIENSE [J].

BALTZ, T ;

BALTZ, D ;

GIROUD, C ;

CROCKETT, J .

EMBO JOURNAL, 1985, 4 (05) :1273-1277

[3] Design, synthesis and antitrypanosomal activities of 2,6-disubstituted-4,5,7-trifluorobenzothiophenes [J].

Bhambra, Avninder S. ;

Edgar, Mark ;

Elsegood, Mark R. J. ;

Li, Yuqi ;

Weaver, George W. ;

Arroo, Randolph R. J. ;

Yardley, Vanessa ;

Burrell-Saward, Hollie ;

Krystof, Vladimir .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 108 :347-353

[4] Synthesis and in vitro antitubercular activity of a series of quinoline derivatives [J].

de Souza, Marcus V. N. ;

Pais, Karla C. ;

Kaiser, Carlos R. ;

Peralta, Monica A. ;

Ferreira, Marcelle de L. ;

Lourenco, Maria C. S. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (04) :1474-1480

[5] Uptake and mode of action of drugs used against sleeping sickness [J].

Denise, H ;

Barrett, MP .

BIOCHEMICAL PHARMACOLOGY, 2001, 61 (01) :1-5

[6] QUANTITATIVE ASSESSMENT OF ANTI-MALARIAL ACTIVITY INVITRO BY A SEMIAUTOMATED MICRODILUTION TECHNIQUE [J].

DESJARDINS, RE ;

CANFIELD, CJ ;

HAYNES, JD ;

CHULAY, JD .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 16 (06) :710-718

[7] 4-Aminoquinolines Active against Chloroquine-Resistant Plasmodium falciparum: Basis of Antiparasite Activity and Quantitative Structure-Activity Relationship Analyses [J].

Hocart, Simon J. ;

Liu, Huayin ;

Deng, Haiyan ;

De, Dibyendu ;

Krogstad, Frances M. ;

Krogstad, Donald J. .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2011, 55 (05) :2233-2244

[8] A COMPARISON OF 3 METHODS OF ESTIMATING EC(50) IN STUDIES OF DRUG-RESISTANCE OF MALARIA PARASITES [J].

HUBER, W ;

KOELLA, JC .

ACTA TROPICA, 1993, 55 (04) :257-261

[9] Synthesis and antimalarial activity of new chloroquine analogues carrying a multifunctional linear side chain [J].

Iwaniuk, Daniel P. ;

Whetmore, Eric D. ;

Rosa, Nicholas ;

Ekoue-Kovi, Kekeli ;

Alumasa, John ;

de Dios, Angel C. ;

Roepe, Paul D. ;

Wolf, Christian .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (18) :6560-6566

[10] Human African trypanosomiasis of the CNS: current issues and challenges [J].

Kennedy, PGE .

JOURNAL OF CLINICAL INVESTIGATION, 2004, 113 (04) :496-504

← 1 2 3 →